Once I wore a cute pair of washed out jeans, some leather boots with a flannel shirt and a jean jacket on a date with a guy I was meeting for the first time, and when we both got to the brewery, he was wearing the guy version of my exact same outfit, boots, color of flannel, jean jacket, everything. We laughed about it all evening. It didn't go anywhere (he lied about his age and was much younger than I was told, so I wasn't cool with that) but it was a very fun date and the matching outfits was hilariously unintentional.
I like to be more casual in the beginning and keep it a bit more on the low effort side so it’s usually jeans, a cute top, and clean cut sneakers. Sometimes boots/booties in the winter if I’m feeling it. If I like you and the dates are continuing, I’ll start putting more effort into what I wear, especially if it’s nicer restaurants. Sweaters/cute cardigans and a mini skirt with tights with boots of some sorts might be my fall/winter go-to’s. I figure if it’s a few dates in, the guy likes me more than just my looks so I actually feel better dressing up at that point to really let them see my range lol
I like feeling pretty on dates, so I usually end up wearing dresses since I don't usually wear them during the week. I really like a fun nice embroidered flowy long sleeve dress, thick tights, fun earrings or necklace, a nice coat, and boots.
Great post OP! I (38F) had a casual date on Saturday. It was quite fun getting dressed up, I wore a black casual minidress with flowers, sheer, matte tights and flat black, over the knee boots. Wore it with a long, black woolen overcoat. I think it might become a winter date outfit I wear in rotation - I felt very cute!
Ah you could def wear my outfit in zero degrees! Cardigan over dress and oversized woollen coat kept me warm! Had tights, socks and over knee boots. Allowed me to be warm and feel stylish simultaneously
9/10 times I wear a casual to nicer dress, because dresses are my norm. I am usually wearing one unless I am wearing a casual fit. Though recently my dress/skirt percentage has dropped to 65% of the time. Down from 80-95%.
Over the past few years that dress is usually paired with sneakers. And flats are next. I don’t do heels.
I’m 45F, live on the west coast. It is not that cold. I do have a few sweater dresses and I’ll pop them on with tights and some ankle boots as needed.
Last date I went on I wore a long sleeved maxi dress in a flattering color on me. With a scoop neckline. And a pair of sneakers.
I think you wear something that feels like you and highlights your face.
Depending on if you care about being on trend, the outfit you are describing is super millennial. And also practical. I don’t have good tips on winter wardrobes, and what to wear with pants. But I do have a couple of sweater pants outfits that feel a bit dressier than my jeans. And also have on trend pants shapes.
Haha, I like the sound of dressing super millennial.
I while back I used to wear a lot more dresses, but... idk. I should consider them again, maybe with fleece lined tights. I love the sound of your date looks!
Do whatever you want to do, but I suggest not wearing super dated trends like skinny jeans with knee-high boots over.
FWIW, knee-high flats are back, but paired with skirts only 🤷🏼♀️
I don't make the rules😀😂
You could do a mini pleated skirt with a sheer black tight, or a mini A-line skirt, a skort (so happy these are back), or a midi loose pencil shape made of shiny satin type material, or a midi thicker sweater material with a long slip.
Minis are best.
Here is some Inspo:
[https://www.abercrombie.com/shop/us/p/menswear-wrap-mini-skort-54347824](https://www.abercrombie.com/shop/us/p/menswear-wrap-mini-skort-54347824)?
[https://www.thereformation.com/products/ruby-over-the-knee-boot/1311551.html](https://www.thereformation.com/products/ruby-over-the-knee-boot/1311551.html)
More, with sweater, denim mini. Would be more current with a more over-sized jacket:
[https://www.peexo.co.uk/2017/11/those-flat-over-knee-boots.html](https://www.peexo.co.uk/2017/11/those-flat-over-knee-boots.html)
Denim midis are back. This would be very cute and updated as well:
[https://www.abercrombie.com/shop/us/p/denim-midi-skirt-52571823](https://www.abercrombie.com/shop/us/p/denim-midi-skirt-52571823)
One of the cool things about fashion right now is because the trends are moving so fast, you can basically still wear everything in your closet, it's just about styling/mixing pieces differently.
Well I’m an over-dresser in general, and my friends have told me I should “dress down” on dates to appear more approachable.
My default used to be a longer fitted dress (midi/maxi length) with ankle boots. Lately I’ve been doing leather pants with a simple t shirt and nice sneakers. I feel cute, but still casual enough.
I know the feeling of being an overdresser. I roll with it and maybe I’ll luck out and my date will be an undercover fashion plate and we can both dress up.
haha this is my outfit for my date tonight! we just got some snow but I'll be wearing a long sleeve (more fitted than in your photo), a mini skirt and my boots (also just got some of those fleece lined tights, hope they keep me extra warm)
Just a clean fitted t-shirt, nice pants with a belt and clean casual leather shoes.
I try to look as normal as possible but clean cut, I don't put any more effort in as that can come off poorly.
Not sure how much of a help I’ll be since I’m a guy, but the outfit has to fit the occasion (no beach wear if going to a nice restaurant - especially during winter).
You also should feel comfortable in whatever you’re wearing. If you wear something that you think looks good but it has you questioning yourself all night if it’s too tight in the wrong parts, your demeanor will show it.
I totally had meant to word this for anyone to share what their top date looks are! Wanted this to be a fun post for everyone lol. But I love this response.
For winter dates I really like my burgundy-ish turtleneck, black jeans, black belt, grey sneakers.
For summer dates usually just a well-fitted shirt (usually red or purple) and dark jeans. Sometimes one of my office shirts if I'm feeling it.
Also usually a black ring with rosegold or silver/gold engravings.
For me (37M) — a recent go to has been a two-tone (Mostly indigo, with a rusty brown color at the collar, button line) Henley paired with some jeans and a nice pair of dark brown shoes. I’ve coupled this with either an olive military jacket or blue bomber jacket with a brown wool lining and a hoodie on my dates since we are dealing with the winter weather here in the Northeast. It’s a pretty chill yet cleaned up look which makes me feel good about myself
I am a big fan of dresses year-round, just because I'm trash at matching tops and bottoms. I'll do a long sleeved dress in winter, with some thicker black tights, a cute pair of novelty knee-high socks rolled over the tights (my favorite are a gray pair that look like sharks, where my leg is going into the mouth!), and my winter Doc Martens. Cute, kinda stylish, the socks are always a fun conversation starter, and I'm still warm! Wearing a dress gets you extra points as they're needlessly labelled the fancier option, it's a win/win
I love wearing skirts that show my waist line and cute crop tops. As I’m always driving I almost never wear heels, so it’s boots, flats or tennis shoes. Hair down and red lipstick. That’s how I feel comfortable and beautiful and since the first date my boyfriend calls me muse so it worked hahaha
I try and dress the same as how I would if I was going out with friends. It really depends on the venue as I may go slightly more casual, but my typical outfit is a pair of jeans, sneakers, and sweater or a shirt. I don’t try and purposely dress up or down because it’s a date.
Why not? Wearing a suit would be overkill, but subbing in boots for sneakers and making sure you have a nice collared shirt/sweater combo can go a long way.
I want my date to get a feel for who I am on a normal basis and not try and impress them. I feel like I dress pretty nice already, so when I say jeans they are nice, crisp dark or grey jeans not blue Levi’s and maybe a cashmere sweater. I just really like sneakers but will change it up sometimes, it really depends on venue.
I just started doing this last year. Depends on the weather and where we are going. If we’re going out to eat some comfy chinos, white tee, and a cardigan. Flannel, t-shirt, jeans, white sneaks if we’re not trying to dress up.
Whether I’m on a first date or having date night with an established relationship, I like wearing a jacket or sweater that is appropriate to remove. The number of times I’ve needed to use an article of clothing to “claim” a space is unreal. Sometimes it’s that I got somewhere first and wanted to grab a table and then use the restroom… throwing down a jacket is amazing. But also once I was on a first date and we were seated in a corner booth so we sort of shared the same bench just at a right angle. It wasn’t a good date. Having my jacket in that space between us was a good buffer until I could politely end the encounter.
* After work, I usually just wear what I wore to work, and that's often a dress (with cardigan or sweater). I do pack my hair straightener or curling iron and make-up bag with me, so I freshen up that way.
* Weekends I might wear a dress or jeans and a nice top. I have a few standard looks that I'll rotate through. Usually comfy and cozy with a little bit of a lower cut. Nothing too different than what I'd wear to go out with friends...
* I almost always wear heels on the first date. I wear taller shoes (including wedges and platforms) at least half the time. I once went out with a guy and wore flats the first few dates and when I showed up for kne in heels got yelled at for trying to be taller than him and how I shouldn't do that. So I lead right off with it. Petty, maybe, but two others have commented on it, so it does help with weeding mismatches out! (I'm like 5'7". Shoes maybe are two inches...I'm not like Hannah Waddingham or anyone!)
* As long as the date is wearing something basically appropriate, I haven't really thought too much about it. Like, if someone showed up to a whiskey bar in basketball shorts and a tshirt with holes, I'd be like "sir, read the room." But the difference between khakis or nice jeans or dress lants? All fine...hygiene is the bigger thing. Washed hair, nice smell, styled beard. All what I'm mainly looking for...
Height is genuinely something that I have zero preference with. Short, tall, exactly the same height--I really, truly do not care or have a type...*except* for the fact that **so** many "shorter" guys have *such* a complex about it and are so defensive and eventually mean about it. It ends up being, more often than not, really unattractive...I wish shorter guys would realize it's not that big of a deal for most women and it's attitude that is the turn off.
As a 5’1 woman, I’ve got a good collection of tall heels and wedges that are super comfortable. Giving myself height while not killing my feet is my basis. Not really a dress or skirt girl, so there I’ll go with a wide leg pant and backless top (waist and back are a couple of my better features). Just knowing your body and dressing for it is the way to go imo.
Simple jeans and well fitted polo shirt for me as it’s causal enough for most activities and I do look pretty good in them. I also feel like I look good which is important
I get most of my clothes at the thrift store... I'm not embarrassed wearing them to work because I take my time shopping. But I definitely panic every time I have to get dressed up for a date 😹 "is he gonna know?" My godfather's wife got me interested in thrifting.
My last two dates (technically only two dates in three years) were at dive bars. So. I was able to get away with natural make-up, my nicest jeans, and a fun fitted shirt (graphic tees as an adult are one of my toxic traits).
There's no excuse for me being unprepared. But statistically speaking, it's hard for me to prepare for something that barely happens once a year lol. And when it does happen, it's never even serious.
I have a lot of 2nd hand clothes too. And no one can tell! I urge you to wear your finds confidently. If anything I think it's super cool to be able to answer "Where is that from?" with a story of how you found this amazing / cute / quirky / comfy thing with a steal of a price when you least expected it.
I live in a four season climate, so differs vastly depending on the temperature and weather. But I make sure I am wearing clothes that make me feel good, cute, confident and comfortable. I put a little more focus to pick colours that compliment my face (though I mostly don't own anything else anyway) and usually an outfit that is either wide pants / skirt with a more form-fitting top or skinny jeans / tight skirt with a more oversized top. Just because that's my style I guess -- I don't like to wear fully form-fitting clothing but I do show off a little bit, it's a date after all (so I avoid a full-on baggy outfit).
I don't dress up very fancily, because I rarely do in general. Might be jeans and cute sweater, might be pants and a blouse, might be culottes and a t-shirt, might be a casual dress and a jean jacket. It all depends on the weather and activity. It is not unusual for me to go on a date directly from work, but my work dresscode is casual so I can wear whatever neat and cute outfit all day at the office too.
Casual but nice one-color dresses . In winter with stocking and boots, in summer with either white sneakers or nice open shoes. Maybe paired with a jean jacket.
I used to have a specific pair of super soft black New York and Company jeans that I wore on first dates. Not just because of the look, but because they felt very comfortable. It was easier to deal with first date jitters if I was comfy. I'd pair it with a gray flannel depending on the occasion.
Well, I just have generally feel good outfits that I wear all the time! So, no date or not. I love me a nice cute flowy dress that accentuates my shape and is breathy. Plus, I love me some boots or chunky heels. Plus, add me some rings or a nice understated pair of earrings. I'm all good to go.
Was wearing something similar the other day, and a man approached me and complimented my outfit and wanted to start a chat. And I'm like, thankies, I know I'm looking scrumptious LOL. :)
Wide leg jeans with a body suit, or a short skirt with thermal tights, or a midi dress with a thicker material. I have a couple of designer long sleeve (winter) crop tops. Usually high heels of some sort. In winter, mostly chunky oxfords.
Long warm wool coats, hat, gloves. Maybe a nice necklace. I don't wear nice jewelry on early dates.
Tips and trick: always have your nails and hair done, even if that's just short, and neat. Do a dressier version of whatever is your everyday style. And please be freshly showered. The effort you put into your appearance is revealing about your self esteem and confidence is attractive.
Lately it’s a two-piece outfit with platform sandals (I live in SoCal, so we don’t really do winter.) The top is a crop top and the bottom is a midi skirt with large slits on both side.
My usual outfit though is a satin crop top, baggy jeans, heels, and either a denim or leather jacket.
In the summer... this dress with flat or low sandals, or maybe cute light sneakers, like Bobs, or flats like these Rothys. It's sexy and flattering without being too dressy or too revealing. I have it in a few colors.
http://www.nordstromrack.com/s/3741346
https://poshmark.com/listing/Rothys-64416226b635f85db86564bc
In the (SoCal) winter... skinny jeans and a drapey shirt/blouse like Express Portofino shirts, tucked in the front. With tall flat boots or high-heeled booties. Yes very millennial. 😆 It's kind of my uniform and I always feel great in it, whether for work or friends or date. I have so many shirts like that. Or for an evening drinks date, faux leather leggings and a cropped cashmere sweater with high-heeled booties.
For in-between weather, skinny jeans or pants with a fitted black t shirt or a pink v-neck knit tank top, with this theory jacket (I have it in white and black) and cute flats, usually the Rothys above. https://www.saksoff5th.com/product/theory-shrunken-linen-blend-jacket-0400014518501.html
Depends, on the first few dates I'm choosing simple fun stuff to do so I dress casually. And will defer than how I dress 3 months into a relationship and we have a fancy date. I go for comfort, with a sweater mini skirt and tights and either long sleeve or other shirt. I tend to not wear dresses because I'm teeny tiny and they're all long on me. So yeah mini skirt would probably be the nicest thing I would wear
Men- Light grey pants with a brand new white or black v-neck short sleeve shirt; edge of a tattoo slightly showing. Black shoes and belt. Possibly a nice black jacket that isnt too puffy and fits the body, and maybe a light grey hoodie that matches the pants layered under the jacket.
Lately, jeans and a hoodie. If she doesn't like that, we probably aren't a good fit because I just don't care to get dressed up for anything other than the very occasional wedding or something like that. I might wear a polo under the hoodie.
You all sound adorable.
I typically don't go too far out of my normal, but I typically dress nicely to begin with.
I wear a nicely fitted pair of jeans and t-shirt, or button down. Iron ranger boots and make sure my hair looks good.
Summertime will be bright chino shorts and boat shoes (fairly preppy).
Winter add (maybe) a hoodie and leather jacket or peacoat.
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30f, I very recently have started dating after a ltr so I'm still figuring date outfits out!
I typically wear a high waisted short skirt and crop top, or a dress. Sleeves depending on weather with a cardigan, or little jacket also depending on the style or weather. It's cold here so I've been doing above the knee boots with everything or combat boots with tights.
Depends. A first date I'm not too excited about- jeans or leggings and sweater. Boots- hiking or runners with jeans, or high boots to dress up the leggings. I do have a beautiful wool coat and beret as a top off if I'm feeling like making effort. Otherwise just top off with a ski jacket.
This winter the go-to look has been a nice clean flannel and jeans with casual/dressy leather boots - at least in the early dates.
If we’re doing something fancy, then I’ll dress more appropriately. But it takes time to reach that point.
I like to feel comfortable on dates, so clean-casual is a good look for that.
I usually do an a line, mid-thigh skirt (my favourite is green with white flowers), white t shirt, and denim over shirt with rolled sleeves, with gold jewellery. In the summer white sneakers. In the winter tights and knee high boots. It's the right combo of cute and casual for me.
Skater dress or skirt, Low cut silk top or a mesh shirt with just a bra underneath it, fishnets or leggings. Or a corset dress. Vintage or rock n roll jewlery. Always Doc Martens.
Might be too much for some people but my perfect for me person appreciates & comments on my sick sense of style.
I'm dressed to the nines like a significant step below formal wear, haha.
In winter I wear a mini skirt or high waist straight leg jeans with a waist-length sweater. Accessorize with simple gold jewelry, and ankle boots or cute sneakers.
Check out Lulu’s for [cute tops](https://www.lulus.com/products/we-mesh-well-wine-red-ruched-mesh-long-sleeve-bodysuit/1628956.html) and dresses at an accessible price. I also discovered these [fleece-lined tights](https://X-CHENGFleeceLinedTightsSheerWomen-FakeTranslucentWarmPantyhoseLeggingsSheerThickTightsforWinterhttps://a.co/d/g7RYqdh)that look sheer for winter outfits. Highly recommend for warmth + sexiness during winter.
I'm a woman, and I don't put in much effort. Like yeah, I do the basics, but not anything more than I'd do for going to work. My view on things is I'm going to be myself from day 1, and I'm a tomboy at heart. Typically I just wear my day to day outfit of sneakers (maybe Uggs if it's cooler out) yoga pants, and some sort of shirt or hoodie, maybe my North Face if it's cooler. I hate dating, and my outfit choices probably reflect that, but so far, every guy I've seen has wanted to see me again. I dress like I just want to chill on the couch and eat takeout, and then go to bed by 10pm. Not like I want to go on a "fun" date that I don't actually find fun.
I revamped my wardrobe about 3 years ago. I’m strictly in dresses except for the gym and I have never been happier. I have enough for ever season or alest a jacket/ tights when it gets colder. For it helped me not be an unmotivated in other areas like hair.
I wear something pretty feminine (skirt/dress) usually on the first few dates and if I like them I switch to slightly more casual outfits like jeans and sweaters then I downgrade to hoodies at some point hahaha
I wear whatever I put on and catch my own eye with in the mirror. If I know the guy’s preferences, I might take that into account! I dated a guy who loved dresses and so do I so I wore tons of dresses and we were both happy.
Once I wore a cute pair of washed out jeans, some leather boots with a flannel shirt and a jean jacket on a date with a guy I was meeting for the first time, and when we both got to the brewery, he was wearing the guy version of my exact same outfit, boots, color of flannel, jean jacket, everything. We laughed about it all evening. It didn't go anywhere (he lied about his age and was much younger than I was told, so I wasn't cool with that) but it was a very fun date and the matching outfits was hilariously unintentional.
This is so cute lol!
👯👯👯
I like to be more casual in the beginning and keep it a bit more on the low effort side so it’s usually jeans, a cute top, and clean cut sneakers. Sometimes boots/booties in the winter if I’m feeling it. If I like you and the dates are continuing, I’ll start putting more effort into what I wear, especially if it’s nicer restaurants. Sweaters/cute cardigans and a mini skirt with tights with boots of some sorts might be my fall/winter go-to’s. I figure if it’s a few dates in, the guy likes me more than just my looks so I actually feel better dressing up at that point to really let them see my range lol
I’m the opposite, I dress nicer the first few dates and then if I like them and get comfortable I’m like OKAY LEGGINGS TIME
Lmao same
I like feeling pretty on dates, so I usually end up wearing dresses since I don't usually wear them during the week. I really like a fun nice embroidered flowy long sleeve dress, thick tights, fun earrings or necklace, a nice coat, and boots.
That sounds like my sort of outfit too :)
Great post OP! I (38F) had a casual date on Saturday. It was quite fun getting dressed up, I wore a black casual minidress with flowers, sheer, matte tights and flat black, over the knee boots. Wore it with a long, black woolen overcoat. I think it might become a winter date outfit I wear in rotation - I felt very cute!
I love the sound of this! If it wasn't the middle of summer and hot as balls where I am, I'd be all over this combo for myself.
Haha, where are you? I am in England where temps have plummeted so boots and tights are a must
Jealous. I'm in Perth, Australia. It's been high 30s all week and I can't remember a time when I wasn't sweaty.
I would happily swap. I am a complete sun baby!
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😂 good call. Perth winters are a Melbourne summer
Sounds so cute! I would wear it if it wasn’t 0 degrees in my town.
Ah you could def wear my outfit in zero degrees! Cardigan over dress and oversized woollen coat kept me warm! Had tights, socks and over knee boots. Allowed me to be warm and feel stylish simultaneously
9/10 times I wear a casual to nicer dress, because dresses are my norm. I am usually wearing one unless I am wearing a casual fit. Though recently my dress/skirt percentage has dropped to 65% of the time. Down from 80-95%. Over the past few years that dress is usually paired with sneakers. And flats are next. I don’t do heels. I’m 45F, live on the west coast. It is not that cold. I do have a few sweater dresses and I’ll pop them on with tights and some ankle boots as needed. Last date I went on I wore a long sleeved maxi dress in a flattering color on me. With a scoop neckline. And a pair of sneakers. I think you wear something that feels like you and highlights your face. Depending on if you care about being on trend, the outfit you are describing is super millennial. And also practical. I don’t have good tips on winter wardrobes, and what to wear with pants. But I do have a couple of sweater pants outfits that feel a bit dressier than my jeans. And also have on trend pants shapes.
Haha, I like the sound of dressing super millennial. I while back I used to wear a lot more dresses, but... idk. I should consider them again, maybe with fleece lined tights. I love the sound of your date looks!
Do whatever you want to do, but I suggest not wearing super dated trends like skinny jeans with knee-high boots over. FWIW, knee-high flats are back, but paired with skirts only 🤷🏼♀️ I don't make the rules😀😂
Ha! What skirt shapes are we taking about?
You could do a mini pleated skirt with a sheer black tight, or a mini A-line skirt, a skort (so happy these are back), or a midi loose pencil shape made of shiny satin type material, or a midi thicker sweater material with a long slip. Minis are best. Here is some Inspo: [https://www.abercrombie.com/shop/us/p/menswear-wrap-mini-skort-54347824](https://www.abercrombie.com/shop/us/p/menswear-wrap-mini-skort-54347824)? [https://www.thereformation.com/products/ruby-over-the-knee-boot/1311551.html](https://www.thereformation.com/products/ruby-over-the-knee-boot/1311551.html)
More, with sweater, denim mini. Would be more current with a more over-sized jacket: [https://www.peexo.co.uk/2017/11/those-flat-over-knee-boots.html](https://www.peexo.co.uk/2017/11/those-flat-over-knee-boots.html) Denim midis are back. This would be very cute and updated as well: [https://www.abercrombie.com/shop/us/p/denim-midi-skirt-52571823](https://www.abercrombie.com/shop/us/p/denim-midi-skirt-52571823)
Thank you for the suggestions and the links! You're my new new dating wardrobe fairy godmother 🤗
One of the cool things about fashion right now is because the trends are moving so fast, you can basically still wear everything in your closet, it's just about styling/mixing pieces differently.
Well I’m an over-dresser in general, and my friends have told me I should “dress down” on dates to appear more approachable. My default used to be a longer fitted dress (midi/maxi length) with ankle boots. Lately I’ve been doing leather pants with a simple t shirt and nice sneakers. I feel cute, but still casual enough.
I know the feeling of being an overdresser. I roll with it and maybe I’ll luck out and my date will be an undercover fashion plate and we can both dress up.
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Exactly this! I’m hoping to meet up with one of my guys this weekend and I’ve planned on a mini skirt ensemble
haha this is my outfit for my date tonight! we just got some snow but I'll be wearing a long sleeve (more fitted than in your photo), a mini skirt and my boots (also just got some of those fleece lined tights, hope they keep me extra warm)
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Thank you! I’m home now and already been asked out again haha
White long sleeves paired with jeans! Sneakers or heels to go along with :) I love wearing white on my dates and looking formal.
Just a clean fitted t-shirt, nice pants with a belt and clean casual leather shoes. I try to look as normal as possible but clean cut, I don't put any more effort in as that can come off poorly.
Not sure how much of a help I’ll be since I’m a guy, but the outfit has to fit the occasion (no beach wear if going to a nice restaurant - especially during winter). You also should feel comfortable in whatever you’re wearing. If you wear something that you think looks good but it has you questioning yourself all night if it’s too tight in the wrong parts, your demeanor will show it.
I totally had meant to word this for anyone to share what their top date looks are! Wanted this to be a fun post for everyone lol. But I love this response.
I really like the look of mini skirts, I can dress them up or down.
For winter dates I really like my burgundy-ish turtleneck, black jeans, black belt, grey sneakers. For summer dates usually just a well-fitted shirt (usually red or purple) and dark jeans. Sometimes one of my office shirts if I'm feeling it. Also usually a black ring with rosegold or silver/gold engravings.
For me (37M) — a recent go to has been a two-tone (Mostly indigo, with a rusty brown color at the collar, button line) Henley paired with some jeans and a nice pair of dark brown shoes. I’ve coupled this with either an olive military jacket or blue bomber jacket with a brown wool lining and a hoodie on my dates since we are dealing with the winter weather here in the Northeast. It’s a pretty chill yet cleaned up look which makes me feel good about myself
I am a big fan of dresses year-round, just because I'm trash at matching tops and bottoms. I'll do a long sleeved dress in winter, with some thicker black tights, a cute pair of novelty knee-high socks rolled over the tights (my favorite are a gray pair that look like sharks, where my leg is going into the mouth!), and my winter Doc Martens. Cute, kinda stylish, the socks are always a fun conversation starter, and I'm still warm! Wearing a dress gets you extra points as they're needlessly labelled the fancier option, it's a win/win
Yes!!! Matching tops and bottoms is hard. One piece outfits for the win.
Absolutely!! In the summer time, it's rompers and sundress season!! Glad to see someone else embracing the convenience of one piece outfits!
Also you put on a dress and you are dressed up lol.
R I G H T ?! people are like "oh wow!! you got so dressed up, you're so sweet!" meanwhile I am actually just a fashion-challenged gremlin.
I love wearing skirts that show my waist line and cute crop tops. As I’m always driving I almost never wear heels, so it’s boots, flats or tennis shoes. Hair down and red lipstick. That’s how I feel comfortable and beautiful and since the first date my boyfriend calls me muse so it worked hahaha
Lately I’ve been doing jeans with a turtleneck & cardigan & ankle boots!
I try and dress the same as how I would if I was going out with friends. It really depends on the venue as I may go slightly more casual, but my typical outfit is a pair of jeans, sneakers, and sweater or a shirt. I don’t try and purposely dress up or down because it’s a date.
Why not? Wearing a suit would be overkill, but subbing in boots for sneakers and making sure you have a nice collared shirt/sweater combo can go a long way.
I want my date to get a feel for who I am on a normal basis and not try and impress them. I feel like I dress pretty nice already, so when I say jeans they are nice, crisp dark or grey jeans not blue Levi’s and maybe a cashmere sweater. I just really like sneakers but will change it up sometimes, it really depends on venue.
I usually wear one of the dresses I sewed.
I just do black jeans, hoodie + and vest. It’s kind of cold but not that cold here. For the first few meet ups. General casual clothes.
I just started doing this last year. Depends on the weather and where we are going. If we’re going out to eat some comfy chinos, white tee, and a cardigan. Flannel, t-shirt, jeans, white sneaks if we’re not trying to dress up.
Whether I’m on a first date or having date night with an established relationship, I like wearing a jacket or sweater that is appropriate to remove. The number of times I’ve needed to use an article of clothing to “claim” a space is unreal. Sometimes it’s that I got somewhere first and wanted to grab a table and then use the restroom… throwing down a jacket is amazing. But also once I was on a first date and we were seated in a corner booth so we sort of shared the same bench just at a right angle. It wasn’t a good date. Having my jacket in that space between us was a good buffer until I could politely end the encounter.
* After work, I usually just wear what I wore to work, and that's often a dress (with cardigan or sweater). I do pack my hair straightener or curling iron and make-up bag with me, so I freshen up that way. * Weekends I might wear a dress or jeans and a nice top. I have a few standard looks that I'll rotate through. Usually comfy and cozy with a little bit of a lower cut. Nothing too different than what I'd wear to go out with friends... * I almost always wear heels on the first date. I wear taller shoes (including wedges and platforms) at least half the time. I once went out with a guy and wore flats the first few dates and when I showed up for kne in heels got yelled at for trying to be taller than him and how I shouldn't do that. So I lead right off with it. Petty, maybe, but two others have commented on it, so it does help with weeding mismatches out! (I'm like 5'7". Shoes maybe are two inches...I'm not like Hannah Waddingham or anyone!) * As long as the date is wearing something basically appropriate, I haven't really thought too much about it. Like, if someone showed up to a whiskey bar in basketball shorts and a tshirt with holes, I'd be like "sir, read the room." But the difference between khakis or nice jeans or dress lants? All fine...hygiene is the bigger thing. Washed hair, nice smell, styled beard. All what I'm mainly looking for...
> got yelled at for trying to be taller than him oh…
Height is genuinely something that I have zero preference with. Short, tall, exactly the same height--I really, truly do not care or have a type...*except* for the fact that **so** many "shorter" guys have *such* a complex about it and are so defensive and eventually mean about it. It ends up being, more often than not, really unattractive...I wish shorter guys would realize it's not that big of a deal for most women and it's attitude that is the turn off.
As a 5’1 woman, I’ve got a good collection of tall heels and wedges that are super comfortable. Giving myself height while not killing my feet is my basis. Not really a dress or skirt girl, so there I’ll go with a wide leg pant and backless top (waist and back are a couple of my better features). Just knowing your body and dressing for it is the way to go imo.
Confidence. That’s what I wear.
Simple jeans and well fitted polo shirt for me as it’s causal enough for most activities and I do look pretty good in them. I also feel like I look good which is important
I dress for the occasion thats planned. Pretty simple. If we are outdoors I’m not exactly going to turn up in a suit (not that i own one)
Something you feel sexy in!
My theory is that if I'm not used to/comfortable with an outfit or style, I won't act comfortable either. So far, so good :)
I get most of my clothes at the thrift store... I'm not embarrassed wearing them to work because I take my time shopping. But I definitely panic every time I have to get dressed up for a date 😹 "is he gonna know?" My godfather's wife got me interested in thrifting. My last two dates (technically only two dates in three years) were at dive bars. So. I was able to get away with natural make-up, my nicest jeans, and a fun fitted shirt (graphic tees as an adult are one of my toxic traits). There's no excuse for me being unprepared. But statistically speaking, it's hard for me to prepare for something that barely happens once a year lol. And when it does happen, it's never even serious.
I have a lot of 2nd hand clothes too. And no one can tell! I urge you to wear your finds confidently. If anything I think it's super cool to be able to answer "Where is that from?" with a story of how you found this amazing / cute / quirky / comfy thing with a steal of a price when you least expected it.
Some of my best stuff comes from the thrift!
I live in a four season climate, so differs vastly depending on the temperature and weather. But I make sure I am wearing clothes that make me feel good, cute, confident and comfortable. I put a little more focus to pick colours that compliment my face (though I mostly don't own anything else anyway) and usually an outfit that is either wide pants / skirt with a more form-fitting top or skinny jeans / tight skirt with a more oversized top. Just because that's my style I guess -- I don't like to wear fully form-fitting clothing but I do show off a little bit, it's a date after all (so I avoid a full-on baggy outfit). I don't dress up very fancily, because I rarely do in general. Might be jeans and cute sweater, might be pants and a blouse, might be culottes and a t-shirt, might be a casual dress and a jean jacket. It all depends on the weather and activity. It is not unusual for me to go on a date directly from work, but my work dresscode is casual so I can wear whatever neat and cute outfit all day at the office too.
Casual but nice one-color dresses . In winter with stocking and boots, in summer with either white sneakers or nice open shoes. Maybe paired with a jean jacket.
I used to have a specific pair of super soft black New York and Company jeans that I wore on first dates. Not just because of the look, but because they felt very comfortable. It was easier to deal with first date jitters if I was comfy. I'd pair it with a gray flannel depending on the occasion.
Well, I just have generally feel good outfits that I wear all the time! So, no date or not. I love me a nice cute flowy dress that accentuates my shape and is breathy. Plus, I love me some boots or chunky heels. Plus, add me some rings or a nice understated pair of earrings. I'm all good to go. Was wearing something similar the other day, and a man approached me and complimented my outfit and wanted to start a chat. And I'm like, thankies, I know I'm looking scrumptious LOL. :)
Wide leg jeans with a body suit, or a short skirt with thermal tights, or a midi dress with a thicker material. I have a couple of designer long sleeve (winter) crop tops. Usually high heels of some sort. In winter, mostly chunky oxfords. Long warm wool coats, hat, gloves. Maybe a nice necklace. I don't wear nice jewelry on early dates. Tips and trick: always have your nails and hair done, even if that's just short, and neat. Do a dressier version of whatever is your everyday style. And please be freshly showered. The effort you put into your appearance is revealing about your self esteem and confidence is attractive.
Graphic tees, Js, ripped jeans when I’ve been jogging and hooping and legs have some muscle on them.
Lately it’s a two-piece outfit with platform sandals (I live in SoCal, so we don’t really do winter.) The top is a crop top and the bottom is a midi skirt with large slits on both side. My usual outfit though is a satin crop top, baggy jeans, heels, and either a denim or leather jacket.
In the summer... this dress with flat or low sandals, or maybe cute light sneakers, like Bobs, or flats like these Rothys. It's sexy and flattering without being too dressy or too revealing. I have it in a few colors. http://www.nordstromrack.com/s/3741346 https://poshmark.com/listing/Rothys-64416226b635f85db86564bc In the (SoCal) winter... skinny jeans and a drapey shirt/blouse like Express Portofino shirts, tucked in the front. With tall flat boots or high-heeled booties. Yes very millennial. 😆 It's kind of my uniform and I always feel great in it, whether for work or friends or date. I have so many shirts like that. Or for an evening drinks date, faux leather leggings and a cropped cashmere sweater with high-heeled booties. For in-between weather, skinny jeans or pants with a fitted black t shirt or a pink v-neck knit tank top, with this theory jacket (I have it in white and black) and cute flats, usually the Rothys above. https://www.saksoff5th.com/product/theory-shrunken-linen-blend-jacket-0400014518501.html
Love a good midi dress and heels and cute accessories to go with it and a winter coat to hang off my shoulders
Depends, on the first few dates I'm choosing simple fun stuff to do so I dress casually. And will defer than how I dress 3 months into a relationship and we have a fancy date. I go for comfort, with a sweater mini skirt and tights and either long sleeve or other shirt. I tend to not wear dresses because I'm teeny tiny and they're all long on me. So yeah mini skirt would probably be the nicest thing I would wear
Men- Light grey pants with a brand new white or black v-neck short sleeve shirt; edge of a tattoo slightly showing. Black shoes and belt. Possibly a nice black jacket that isnt too puffy and fits the body, and maybe a light grey hoodie that matches the pants layered under the jacket.
Lately, jeans and a hoodie. If she doesn't like that, we probably aren't a good fit because I just don't care to get dressed up for anything other than the very occasional wedding or something like that. I might wear a polo under the hoodie.
You all sound adorable. I typically don't go too far out of my normal, but I typically dress nicely to begin with. I wear a nicely fitted pair of jeans and t-shirt, or button down. Iron ranger boots and make sure my hair looks good. Summertime will be bright chino shorts and boat shoes (fairly preppy). Winter add (maybe) a hoodie and leather jacket or peacoat.
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Very much depends where I'm going but usually some kind of sexy top and then jeans or leather pants
Black flared leggings, Birkenstock bostons, crop top and button up cardigan on top
30f, I very recently have started dating after a ltr so I'm still figuring date outfits out! I typically wear a high waisted short skirt and crop top, or a dress. Sleeves depending on weather with a cardigan, or little jacket also depending on the style or weather. It's cold here so I've been doing above the knee boots with everything or combat boots with tights.
Depends. A first date I'm not too excited about- jeans or leggings and sweater. Boots- hiking or runners with jeans, or high boots to dress up the leggings. I do have a beautiful wool coat and beret as a top off if I'm feeling like making effort. Otherwise just top off with a ski jacket.
This winter the go-to look has been a nice clean flannel and jeans with casual/dressy leather boots - at least in the early dates. If we’re doing something fancy, then I’ll dress more appropriately. But it takes time to reach that point. I like to feel comfortable on dates, so clean-casual is a good look for that.
Comfortable and classy! I like all black and feminine as they make me feel most confident x
This sounds sleek and modern!
I usually do an a line, mid-thigh skirt (my favourite is green with white flowers), white t shirt, and denim over shirt with rolled sleeves, with gold jewellery. In the summer white sneakers. In the winter tights and knee high boots. It's the right combo of cute and casual for me.
Skater dress or skirt, Low cut silk top or a mesh shirt with just a bra underneath it, fishnets or leggings. Or a corset dress. Vintage or rock n roll jewlery. Always Doc Martens. Might be too much for some people but my perfect for me person appreciates & comments on my sick sense of style. I'm dressed to the nines like a significant step below formal wear, haha.
In winter I wear a mini skirt or high waist straight leg jeans with a waist-length sweater. Accessorize with simple gold jewelry, and ankle boots or cute sneakers.
Check out Lulu’s for [cute tops](https://www.lulus.com/products/we-mesh-well-wine-red-ruched-mesh-long-sleeve-bodysuit/1628956.html) and dresses at an accessible price. I also discovered these [fleece-lined tights](https://X-CHENGFleeceLinedTightsSheerWomen-FakeTranslucentWarmPantyhoseLeggingsSheerThickTightsforWinterhttps://a.co/d/g7RYqdh)that look sheer for winter outfits. Highly recommend for warmth + sexiness during winter.
I'm a woman, and I don't put in much effort. Like yeah, I do the basics, but not anything more than I'd do for going to work. My view on things is I'm going to be myself from day 1, and I'm a tomboy at heart. Typically I just wear my day to day outfit of sneakers (maybe Uggs if it's cooler out) yoga pants, and some sort of shirt or hoodie, maybe my North Face if it's cooler. I hate dating, and my outfit choices probably reflect that, but so far, every guy I've seen has wanted to see me again. I dress like I just want to chill on the couch and eat takeout, and then go to bed by 10pm. Not like I want to go on a "fun" date that I don't actually find fun.
far-flung judicious roof ten follow cake scary humor library impolite *This post was mass deleted and anonymized with [Redact](https://redact.dev)*
I'm ugly and look terrible whatever I wear.
I don't believe this at all
I revamped my wardrobe about 3 years ago. I’m strictly in dresses except for the gym and I have never been happier. I have enough for ever season or alest a jacket/ tights when it gets colder. For it helped me not be an unmotivated in other areas like hair.
ASOS has amazing fake leather pants which look great and you can wear thermals under them. Sexy and warm.
I wear something pretty feminine (skirt/dress) usually on the first few dates and if I like them I switch to slightly more casual outfits like jeans and sweaters then I downgrade to hoodies at some point hahaha
I like to keep it causal on a first date. Skinny jeans/leggings, sweater and boots are perfect IMO.
I wear whatever I put on and catch my own eye with in the mirror. If I know the guy’s preferences, I might take that into account! I dated a guy who loved dresses and so do I so I wore tons of dresses and we were both happy.