I’ve been on a few first dates lately, and it got me thinking about what I typically wear for them. If it’s someone I met online and don’t know if I’ll like them or not, I usually wear jeans/capris and a cute top, but not a revealing one. If it’s someone I’ve met in real life and know I’m interested in, then I try to make more of an effort to look good, and possibly wear a top that is more low-cut. Sometimes I wear heels, or other times cute flats. Cute boots in the colder months. Most of my first dates have been to casual places, so I’ve never worn a dress or skirt.
So, what do you usually wear on a first date? Do you have a go-to outfit?
LemonVibe 
[I usually wear clothes š
Anchorage is (if I remember correctly) the #1 worst dressed city in America. If people were to look at my non-work attire, I think they’ve judged our city accurately. Yes, Anchorage has some snazzy dressers, but I am most comfortable in jeans, a t-shirt and a flannel shirt over it (with sneakers on my feet). Dressing up for me is clean, non-holey jeans, and a nice-ish shirt. Maybe a tank-top and cardigan.
I once wore a black, sleeveless cocktail dress and 3 inch stilletos to a get together (we called ’em GTs). It was an “Opposite Theme” GT that a bunch of us organized online. My brother was my escort and true to form, he wore a tux (with tails and tophat). We all met up at a bar we’d never gone to before. There was a hippie, a farmer, two conservatively dressed folk, one goth, us snazzy dressers, one guy in a pair of daisy dukes (it was January!), we looked hilarious!
My advice is to wear whatever you feel most comfortable wearing. Yes, dress nicely, but dress appropriately. You don’t want to wear a dress, heels and pearls to a go-carting event, nor do you want to dress in overalls to a cocktail party. Everyone has midrange clothes that can pass for most semi-formal/dressy-casual events.
[Well, first of all, I am glad you are considering your attire. I feel like these days people just kind of wear whatever, and I think clothing is a great way of saying something about yourself without ever actually saying something.
The first thing you must consider is your location/environment. If you are going to a nice, fancy restaurant, classy dress is in order. My go-to has always been black. I find that black tends to go with many things so I can wear a black dress, but then add my own flare with an exciting pair of heels. I have found that I am most comfortable taking a “risk” on heels when it comes to going out. I find that a nude heel really elongates the leg. I keep my attire pretty classic, but tend to have a super-awesome pair of shoes on. But, go with what your style is. You should be able to walk and sit in anything you wear. You should exude confidence in your outfit. I see lots of women who look fabulous, but then they can’t walk in their shoes, let alone sit down at a table. You need to wear your clothes, not the other way around. Keep in mind that you want your clothes to represent who you are, not who a model in a magazine is, or who you think this person wants you to be. Be you. And a basic rule to follow is to show of a bit of skin either on the top or bottom, but certainly not both. Cleavage up top, or show off your amazing legs. But don’t wear a short skirt and show off the boobies. No, no, no.
If you are going out to a more casual event, I like to wear a casual, flowy dress with wedges or sandals(leather, not rubber). This says, “I am fabulous, but I don’t really try.” Also, you can never go wrong with a button down shirt paired with khaki shorts and either wedges, sandals or a cute pair of flats(like Tom’s or a cute pair of sneakers). Another go-to look is a great pair of dark jeans, with a basic tank top and a cute pair of heels or flats. Discover the areas of your body you like. I like my arms, but don’t like my stomach, so most of the time I will wear something that shows off my arms, but hides my stomach. I know I wouldn’t be comfortable if I wore something tight.
For a great wardrobe that can be mixed and mingled I would suggest adding the following to your closet. These things are worth investing in: A great little black dress, a perfect pair of dark jeans that hug every curve perfectly, a pair of casual khaki shorts, a nice casual button up shirt, a few pairs of heels that you can walk in and are stunning, a maxi dress, a little black cardigan, and a push-up bra.
Not that I have ever thought about any of this;)
[I lean more towards the casual side, unless I know that we’re going somewhere fancy, or to the bars (in college towns here, dressing up for bars are the norm since it’s one of the few times we have an excuse to wear some nice-ish stuff!) then I’ll pull out a dress or skirt or dark jeans and nice top.
My go-to is skinny jeans that fit just right, (I have a fuller butt than boobs..) that are more darker wash unless we’re day trip dating, a neutral or striped cardigan, and a statement top with/without bold accessories. I like a neutral whimsical style, if that makes sense. I like details and patterns, like lace or lattice, and thrift a lot, so my style could be weird. I keep my outfits pretty simple or plain besides one or two pieces that stand out.
Basically, I try to wear something that gives me confidence, that I know is cute, and that I feel comfortable in. Last time I went on a date with a shirt I had to keep fiddling with and it just KILLED me.
also, when I have no clue what to wear, I visit polyvore.com. I sometimes ask for outfit ideas for certain events, and the community answers! It’s nice if you want some inspiration for clothes.
[I work in a place that requires me to look like a heroin addicted undertaker at all times, (all black, shirt, tie, waistcoat, the works) so I tend not to wear anything fancy unless I absolutely have to.
Usually I’ll wear one of my t-shirts with something pop culture related on, because it can help me decide if a relationship is going to work. I once went out with a girl while wearing a Spider-man t-shirt, she looked at it and asked what it was. I knew right then, it wasn’t going to work.
[My attitude on this has all to do with how much effort I put in. On a first date, I don’t want to put in that much effort because I don’t know the guy well (or at all), and I don’t want it to look like I put in that much effort, either, because I don’t want to give him the impression that I’m desperate or trying too hard. That said, I usually opt for jeans and a casual top under a blazer, or if I feel like wearing a dress, it’s never one of my “fancy” ones, and it’s always with flats.
The other thing is that you want to be comfortable, and yes, you want to take into account your surroundings. If we’re going to go walking in the park on a windy day, I’m not going to wear a dress. If we’re going to be drinking in a bar, I’m going to wear jeans because I’m more comfortable in them, both figuratively and literally.
The key is finding something that makes you look good, but not too good, know what I mean?
[There has to be a joke about “first date, wear a condom” somewhere in there, right? No? The pieces are there, you can put something together.
Anyway, I think two good rules for first date apparel are;
1- Dress appropriate for the activity. Example, if it involves a lot of walking you probably don’t want to wear heels.
2- Wear something that you’ll feel confident in. You don’t want to feel uncomfortable, physically and mentally. I can’t speak for everyone but I assume confidence is a turn on for some people.
[This is a question I can NOT answer… seeing as how I have no “outfits,” don’t date, and would certainly never have anything to do with someone who would judge me on my clothes…
However, I must agree with the first poster… CLOTHES.
Really, I wear my nice jeans (Lucky’s, they make my ass look fantastic), a cute top, and shoes are completely dependent on the activity.
I’m so unhelpful.
[This will probably get me labeled as “sexist,” or something, but this is a topic women generally put wayyyyy much more though/worry/stock into than straight men. The simple answer is: wear what you feel most comfortable and attractive wearing. That confidence will come through, and help way more as far as him finding you attractive then whether the shoes match the top.