People who generally dress casually, what do you wear on a first date?

  1. Jeans and a black tank top! Wear it on almost every first date - no need to think about what I’m going to wear and it’s one of my favorite outfits.

  2. Same here!! Or a black long sleeve shirt in colder months. It’s simple. I feel good and look cute. And you can add accessories to dress it up a little if you’re into that.

  3. I'm going to go ahead and assume you're a woman. I don't think a guy can get away with a tank top on a date.

  4. Same here! I usually wear jeans because I feel like it’s important to present myself authentically. in the summer I’ll opt for shorts to accentuate my long legs!

  5. Whatever you’re most comfortable in and makes you feel like you. I wear dresses a good majority of the time but I wore jeans and a long sleeve black shirt on my first date with my husband 🤷‍♀️

  6. I live in a humid climate and often wear dresses purchased at outdoor equipment companies. They wick sweat. Sexy I know. But I’m reasonably dressed and not sweaty!

  7. My wife's very casual, describes herself (unfairly, IMHO!) as a "passable scruff", but then I'm very casually minded too. For our first date we were both wearing jeans, her with a nice top (sorry to say can't remember exactly what, not a T-shirt but not some fancy silk extravaganza either), me with a T-shirt under a thin sweater. Basically we both upped our game from our default by...a bit, but not too much. Like the best version of our normal clothes, rather than something we wouldn't normally wear or wouldn't feel comfortable in. Nothing to be gained by giving a false impression of what your "normal" is.

  8. I have a go-to first date outfit, it’s a casual, super comfy black dress, I wear it with black tights and flat heel boots. If it’s cold I wear a coat over it etc. pretty easy and comfy and cute and means I look good and like I tried but I don’t actually have to put a ton of effort into finding a date outfit every time👌

  9. You should wear those clothes which makes you the most comfortable. Because the most important thing during the date is to relax. And comfortable clothes can help you achieve that.

  10. I usually go for the nicest version of what I wear normally and that’s appropriate for the venue. No need to wear something you’d typically not wear and give them a false impression.

  11. This. I wear nice pants, 'cause I like to when I dress nice. I don't wear a skirt or dress. That's def not the me that meets new people lol.

  12. Dress for the relationship you want to be in! If that means jeans for you, go for it. Lots of guys show up for coffee dates in a tshirt and jeans, so you should have no trouble finding someone who prefers that mode of casual dress.

  13. Girl, have you spent much time in South Bay? I felt like such a ragamuffin the last time I went out to Santana Row after work with a friend. I think I was wearing a dress or skirt. People really dress up there.

  14. I feel this. I usually wear a nice but casual tank and jeans. I do like the occasional dress up, but for a first date I feel that’d be overkill here, though really depends on the context. Most of my first dates have been pretty casual - coffee shops, etc

  15. I'm in the Bay Area as well. When coming to a date from work, I usually just ask the girl I'm meeting if she "finds guys in business clothing attractive". If I don't get a heart eyes or at least a winky face, I dress down to jeans, t shirt, and a casual "workman" shirt over.

  16. I had a first date recently and had mentioned in the lead up that I'm a pretty casually dressed kinda person. I wore jeans, converse and a fairly relaxed shirt. He ended up in jeans, trainers and a tshirt. It was just meeting for drinks at a pub. If we'd been going somewhere different then maybe I'd have swapped the converse for flats. I get nervous enough meeting someone knew, I always aim to just wear something I'm comfy in.

  17. Personally, I just wear my "normal" clothes; typically consists of black jeans, some kind of black t-shirt/hoodie, and (usually) a hat. This is how I dress all the time. Im not going to go out of my way to wear something abnormal/out of character just for the sake of potentially impressing a stranger. It would also give a false impression of my style and personality.

  18. I'm the same way. I never spend more than 20 minutes getting ready for a first date. I had a third date with a guy recently and he asked me if I had any other types of clothes in my wardrobe, and when he'd be able to see me in a dress. Although I have many dresses and something for every occasion, I prefer comfort and was turned off by the inclination that I should dress a certain way for someone else's preference. If you don't like me as I am, find someone that fits your standards.

  19. Jeans and a solid color tank or t shirt depending on the weather. Today I’m wearing a v neck to be vaguely sexy lol. But I also accessorize, subtle jewelry and a designer clutch so they know I’m a little bougie ;)

  20. I really want to go on a first date where athleisure is acceptable! That's usually no bueno unless you're asking someone to go hiking and that seems sketch for a first date!

  21. Depends on the date. If I can, I try to make our first date something outside and active (so I wear work out stuff or something).

  22. Skinny jeggings and a flattering top. Basically I adjust my top/shoes to match the type of date. If weather allows I am almost always wearing a flattering leather jacket because it’s so easy to dress up and down.

  23. Jeans and a nice shirt/blouse, cute sweater…(depending on the weather)… and a cute pair of sneakers … I keep the first dates usually in a casual place. I don’t go all out for a first date

  24. I saw this awesome lesbian couple on what was clearlyyyyyy a first date last weekend. One of the women was full dress, heels, whole nine yards. The other woman was in jeans, v-neck white tank top, and flannel over shirt effortlessly like draped off one shoulder the whole time, with chunky boots. They both looked fucking fantastic.

  25. Yes!Rule I go by: pairing it with kitten heels (or pointy flats, depending how tall is my date lol— I’m tall and don’t want to be intimidating from the start) and silk blouse in the evening or with the shirt and loafers/sneakers during the day.

  26. Elevated casuals. Often a really nice (maybe Jil Sander) black T or collarless button up, and strait pants. I'd never wear shorts to a first date unless it were on the beach.

  27. What I normally wear.. it feels too uncomfortable to really dress up. So i try to look nice but nothing too special

  28. I don't live in a dress-up kind of city. It's a place where a lot of people wear a sports-team t-shirt and shorts with sandals on a night out. If it's a casual coffee date, I'll just wear a nice t-shirt or button-down shirt. I'll put on a dress shirt and dress slacks for a more upscale restaurant or similar, but generally, things here are more casual.

  29. Uh wear whatever you find comfortable. Atleast that's my take on it, the last date I went on I wore nice slacks and a button up shirt. She wore shorts, t-shirt and flip flops didn't bother me one bit.

  30. Every single first date I go on I wear the same thing. Slip on sneakers, jeans, and a shirt (usually a henley, or a well fitting all black T). When it gets cold I will switch to maybe a long sleeve shirt, or a zipup.

  31. Casual, but then a necklace or earrings and I try to make sure my hair looks tidy even if it's in a ponytail

  32. Jeans, nice sneakers, and a polo shirt or long sleeve shirt. Not much of a button-down guy, except for formal/fancier situations. If it’s too hot, I’ll wear chino shorts and a polo or solid-color shirt.

  33. As a guy, its nice to see that you put in some effort, just as I do to make sure the date goes well. That being said, as a guy, I don't really care much about what my date wears as long as you don't look like you rolled out of bed.

  34. I really like finding cute rompers because I’m the same way, not a fan of dresses or skirts. Rompers are pretty comfy (aside from going to the bathroom that’s kind of a pain😭) and look cute/more girly while still feeling casual.

  35. If they’re taking me out to dinner, and it’s a relatively nice restaurant, I’ll wear a light colored dress like a slip dress type of thing but keep my accessories casual. Other dates like to a bar I’ll wear some cute pants that are may be a color or sort of casual, and a tank top or some sort of cute flattering top with it. agree with casual first.

  36. Jeans and t shirt is perfectly fine. Just remember do your hair and wear light makeup to enhance your beauty. Have fun!

  37. I'm a guy, but I think this applies to women, also. I like having a collection of printed T-shirts that are sharp colors and fit around things that I like to do. I know it sounds corny, but, like, I'll wear a punk cat T-shirt if I'm going to a punk show, or I'll wear a video-game themed shirt if I'm going out to the arcade, for example. That way, it kinda acts as an ice breaker when people mention my shirt and it's usually flattering by way of context.

  38. First impressions are foolish to me. I'm not going to portray something I am not and set up an expectation because thats how we met. I go in whatever I'm wearing that day, which is usually jeans, a band t-shirt with the neck cut off, and whatever hoodie I have and some sneakers. If they don't like it, too bad.

  39. I actually do prefer to wear dresses or a "girly" outfit but a lot of my first dates are right after work. I'm a therapist/social worker for kids at a non-profit. So I usually wear nice jeans and a cute top with some fun earrings/jewelry. And try like the Dickens not to spill coffee or get play-doh all over myself. I'm not always successful. 😄

  40. I'm not a woman, but I like seeing women show up in jeans and a nice top or sweater. I'm a jeans and pollo kind of guy, so if she shows up in a dress it feels too dressy for me.

  41. Everyone has their own taste in casual. But if you're comfortable with jeans and nice shirt, then go with it. I actually like a girl in jeans.

  42. I’d say, do whatever you feel comfortable doing… if it’s not okay with him, it’s not the right one for you!

  43. Glad to read I’m not the only one using “repeat” outfits every first date!! ;) I wear my favorite pair of mom jeans, casual flat sandals, and then a black silk camisole top tucked in. I curl my hair to be loose waves and with makeup, plus a cute purse, I’m on my way and ready in 30 mins tops.

  44. I recommend picking a casual date spot if you wanna dress casually! But if you’re going somewhere that doesn’t allow jeans or is more upscale, I might throw on my creepers instead of heels or I always love a good dress pant/white tennis shoe combo with a simple top. Wearing nice jewelry usually dresses an outfit up too, I like to buy necklace and earring sets and then I throw on a nice watch. Dresses up my casual look in a pinch for sure.

  45. I always wore a black bodysuit, ripped jeans, vans or black booties. Usually a dainty necklace or two. And rings. If it was cold outside then a leather jacket or a jean jacket depending on the pair of jeans I chose.

  46. Depends on where the date is. Since my first dates are typically at one of my favorite restaurants, suit and tie. Dress code.

  47. I generally wear some variety of long sleeved button-up with the sleeves rolled up to the elbows. Slacks or shorts and shoes or sandals will vary by plans and weather.

  48. In fairness, I’m a man. I typically wear a shirt sans tie and pants for weeknight dates because I’m coming from work. On the weekends, I’ll wear casual shirts that I leave untucked. To me, this is fairly casual. But I also consider business casual to be shirt+tie. I dress the way I dress because of work, and because it’s not too far off what I grew up wearing.

  49. Sport coat over a t shirt with a pair of jeans or business casual pants. It's easy, looks dressed up, and is comfortable.

  50. It all depends on what we are doing and the season. So my go-to outfits range from jeans and a cute top (to take away from my gut) with keds sneakers or a cute short dress with keds or NB sneakers, in the summer. Winter, long wool skirt with turtle neck and ankle boots, or jeans with a nice sweater.

  51. Jean shorts and a tshirt! A first date should be casual and comfortable. I don’t want to put tons of effort in and agonize over outfits for a person I don’t even know.

  52. My first date with my girlfriend consisted of both of us being in our work clothes. We both got dragged in for OT on a Saturday and were off around the same time. We met at a Barcade, directly after. It was good. (So I was in construction garb, and she was dressed for walking dogs)

  53. The clothes that make you feel the most confident are the best! Usually I go with a pair of skinny jeans, crop top (with a long cardigan), and some chunky heeled shoes.

  54. I pretty much wear my favourite jeans, a black top, black wedge shoes (booties in the winter), jewelry and red nails on a first date.

  55. Leggings, sweater and Birkenstocks. It’s what I wear 95% of the time and like to be comfortable. I figure it will work for the right person. So not a dress and heels person.

  56. Most of the time my first dates dressed like they didn't care. On the second date they would put in a lot more effort. I think this is the way to go and I respect it. I don't care what you look like the first date as long as I can tell it's the same person from the pictures.

  57. I'm quite comfortable in skirts and dresses so maybe not in your group of people which generally dress casually but when it's too cold or not the right setting I'll wear jeans and a loose knit jumper (usually sand or pale pink to keep it feminine).

  58. Nice jeans, like darker and tighter (new), dressier shoes like cute sandals or flats (I’m tall), and a girly/ruffly silky shirt. Maroon or dark red looks good on me. If you do black, embellish with a necklace or cool earrings. And good but unobtrusive perfume. I would smooth/straighten my hair.

  59. I usually wear jeans and a cute top. I’m a boots person, which can dress up a casual look. If it’s cold, I bring a nice jacket/sweater. Hats also help bring an outfit together depending on your style.

  60. Jeans and a nice black top with boots. I mean honestly you can never go wrong with "jeans and a nice top" 1st date you want to be as comfortable as possible. Good luck xx

  61. I dress casually but my casual is always a comfy dress. So I don't really need to change into a more formal dress or anything like that for dates. It's more a matter of shoes. Instead of flip flops, I wear, heels.

  62. For me, it’s all about venue and comfort. As long as I meet what I feel is the dress code for a venue and am comfortable in what I choose, I’m good to go. While I was actively OLD, that looked like a casual dress in the summer (hot weather climate) or jeans, flats, and a nicer top when it was cold. Maybe altered up or down for a more casual or fancier place. Otherwise, I kind of stick to a “first date uniform” to avoid overthinking it.

  63. I usually do some kind of jeans (light or black usually) or jean short. I'm still on the high waisted train, so usually I'll pair them with some kind of short blouse (like a loose polyester or linen tank top). Something a bit breezy where I'm not likely to flash my stomach.

  64. I get cold fast, so I usually opt for jeans and a sweater (not hoodie). In summer, I usually wear shorts and a cute tank/tshirt with a jean jacket

  65. My kind of lady!! On first dates I reassure the lady I’m going out with it is totally ok to dress casually. They are always glad to hear this.

  66. I always try to make some effort so I go smart casual at least it will be appropriate for whatever date. You want to make some level of effort. Don’t be lazy, it shows you have some level of interest otherwise it gives of the wrong idea like you’re not keen

  67. I'm 34F and dress pretty casually outside work, and my go-to first date outfit is jeans and a nice top. Usually paired with ballet flats, a leather jacket or blazer, and my usual jewellery (silver stud earrings/necklace/ring). For me that feels like it hits a nice balance between being casual but also a more elevated version of my everyday look of jeans with a T-shirt and trainers/jumper and flat ankle boots.

  68. I love dressing up but to me the key on any outfits is that you’re comfortable! No point in looking cute if you’re going to be pulling your skirt down or things are going to be slipping. Adds stress to the already nerve racking experience.

  69. 32M. Nice jeans and a polo shirt. Still casual, but it's nicer than a band tshirt. But really, what you're comfortable in I think is a lot more important as you can be yourself.

  70. Whatever I can wear to work or with my girls, i wear to first dates. Most of my first dates are a walk on a trail or some sort of activity, so I wear the most comfortable clothes so I can have fun.

  71. Jeans or leggings and a t-shirt or tank. I don’t wear makeup on first dates anymore either. I’m not trying to impress someone with my looks. I’m trying to see if we vibe personality wise. If they’re going to be concerned how I look they aren’t right for me.

  72. Male here. I usually wear a pair of jeans and a short sleeved polo shirt with a print on it. First dates have always been coffee/walking dates for me though, so nothing that required any kind of formal wear.

  73. Shorts or jeans and a t shirt and slip ons. I usually suggest something low key though. I’m not trying to misrepresent myself. What you see is what you get.

  74. Usually it depends on the setting for me, if we're just meeting at Starbucks I'll dress casual, if we're meeting somewhere nicer I'll wear jeans with a dress shirt and the sleeves rolled up.

  75. Sexy jeans (fitted or not- whatever you prefer) and a sexy black top (again, your preference. Tank top or long sleeve, etc). The key is to feel comfortable but sexy.

  76. Guy here. 👋🏻 For me, it depends on the date/activity. I have a barcade in L.A. I really like, so if I’m picking I will choose there. Since it’s a casual environment, I dress casual, which for me is usually casual khakis and a nicer casual shirt with buttons. I also wear a hat or ball cap. I like to be casual anyway, so if casual dress is a dealbreaker at least we get it out of the way on the first date.

  77. I wear exclusively black joggers or yoga pants and a black or maroon colored long t every day (I am a female who likes other female so take this response with a grain of salt) Dressing up is just not something I enjoy nor have ever had to do. Even with family events my mom was adamant on me wearing what I was comfortable with, of course it was appropriate just not as dressy as others. I hate that clothes and dating go hand and hand. If I can't be myself I don't want to even try. I'm not trying to impress anyone. I am who I am. I have no other shoes at the moment than sneakers. My body frame and overall general look is not a girly look. I love to wear make up but the rest of very androgynous. I'm not changing who I am or my comfort for anyone. Ironically I attract girly girls which is my type so it works for me

  78. I have one top I wear to first dates and another top I wear on second dates. That way I don't end up wearing the same thing twice on the first two dates and I don't have to keep track of it.

  79. Wear your nicest jeans and a shirt then. Maybe also make sure to go to a casual restaurant, or make plans to go somewhere that you wouldn't be dressed out of place for though.

  80. I dress either relatively casually or somewhat fancier than casual, but no suit or anything - just appropriate enough.

  81. As a guy, I pretty much wear the same thing I wear to work. A decent pair of khakis and a nice collared shirt.

  82. I always dress my looks up with a leather jacket or my black levis sherpa denim jacket. It always somehow makes the look more dressy.

  83. For my first date with my now partner, I wore a yellow oversized "Mr. Roger's" cardigan, tshirt tucked into my cropped Mom jeans and ankle strap shoes

  84. I think you should be yourself but also dress for the occasion. So absolutely dress casual if you’re meeting at Starbucks or a dive bar ( I think dressing up would actually be dishonest if this is not the way you would normally dress), but if the date is at a five star restaurant or something else upscale, then definitely dress more formally.

  85. Eww. She's not an escort. How about both people attempt to look nice while feeling comfortable, confident, and authentic so they can have fun and show each other a good time.

  86. I am a jeans and a t-shirt kind of girl..I typically will wear my best fitting jeans in the darkest color a white t-shirt with a cardigan or a Chanel jacket with a statement piece of jewelry. Long chain with a lion or multi strand chain necklace. I keep my earrings modest if doing larger necklaces. I do a natural makeup look. On subsequent dates I will do graphic tshirts that communicate my personality more or do more flamboyant make up. Don't set a standard by wearing a dress if that is not your style.

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