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What To Wear On A First Date

A bad date for Carrie; Photo - HBO

Just what woman needs: Reasons why that first date went so badly - it was the way you were dressed! The Post asks some guys how women should dress on a first date and the answers are all over the place: "A skirt says there's been too much effort" while "I think summer dresses are pretty sexy, the thin patterned styles especially." Or "Black may be most New Yorkers' favorite color, but that doesn't make it date-worthy" and "I'm a huge, huge fan of stilettos" but "The most important thing on any date is that you feel confident - not to mention comfortable" (Gothamist holds firm that black is comfortable and confident).

Gothamist wonders, since many first dates happen after work, should a gal get all dolled up, for everyone at work to comment, "Oooh, are you going on a date?" and then be subject to post-date inquisition? Our advice: Wear a favorite outfit that wouldn't be too out of place at work but that doesn't paint you as a bore. Stilettos are hot, but let's face it, you've got a long day ahead. You could bring them to the office, but then you're walking out of the office in them, which would still raise questions. That's where the Post's "Go for comfort" maxim makes the most sense. And, really, fashion is the least of your worries on a first date.

And while Gothamist's XX factor may be bitter, we must admit we're glad that metrosexuality has ruined straight men's self-perceptions for at least the next few seasons.

What do you wear on first dates?

Contact the author of this article or email tips@gothamist.com with further questions, comments or tips.

Comments [rss]

  • john

    im going on a first date this week and wondering if i should wear a condom in advance or put it on after she invites me in for a coffee



    any tips would be helpfull

  • madrid

    I'm going on my first date with this guy, and were off to the movies but im nervous that he wont be attracted to me. and he may not like my fashion -alternate. but i like him heappppss!

  • If I'm putting too much thought into what I'm going to wear, it means I've got way too many expectations the date can never live up to anyway...that's when I take a deep breath, pull on my favorite jeans, a top that shows off my shoulders and stop thinking so much!

  • roe

    : astonished : Gang, you're all overlooking the obvious: what you wear on a first date is dictated by where you're going. For example: museum and coffee, stilettos are pretty much out -- who wants to "clickety-click" around the Met?



    If you're meeting to play pool, a low-cut tank is also pretty much out, unless you want to give both your date -- and the entire bar -- a reeeeeeally good view of your "assets." (I have made this mistake. Fortunately, it was about three months in, and we laughed about it later.)



    Even if it's a dinner date, the place dictates my outfit: casual or fun means jeans and a cute top, upscale or romantic means skirt. If you don't know where you're going: cute pants, kitten heels and a nice top are never wrong.



    Easy-peasy, see? :)

  • I'm partial to the "Fancy a Shag" tee shirt from Notting HIll.

  • spence

    a sun dress in that red & white checkered tablecloth fabric, with underwear that matches, some of that lotion that makes you glow and look gold-ish, slightly kinky shoes, small ankle tattoo, and perfume that makes you smell like cinnamon. -or any other deal that makes you look cute and very mildly kinky. --- or just the lotion and the shoes, depending... :)

  • I once ruined a date by wearing a tie to brunch. She was wearing a dumpy a-top and jeans. I think she mistook my narcissism for over-earnestness. Quel dommage!

  • miniapple

    I think my eyes must be tricking me - instead of noticing the SJP alien claw, I thought it was Madonna having a date with Tony Blair!

  • Jellyguy

    Diana, I tried the skirt-and-feminine-top combo once. The result was disheartening.

  • mel

    The day I was supposed to have lunch with a guy I had met over the internet, I made sure to get there early so I could check him out.



    Once I saw the loafers, I was out of there.

  • erikka

    Why isn't this aimed at men? C'mon ladies, how many times have you showed up dressed to the nines and your date is wearing a stained t-shirt, old chucks and jeans that haven't seen the laundry since the Clinton administration? Women aren't the ones who need advice here.

  • Whoever said that a white button-down and jeans can go for both sexes, I disagree. Guys should never tuck their shirt into jeans. Ever. Unless you're from Boston, in which case you kind of have to, unless you're wearing khakis. And don't forget the hideous black shoes with white socks.



    Tight t-shirts, preferably with holes, are great unless you are a girl with humongous boobs. Then you should just go for something really low cut.

  • I find that pairing a colorful, feminine top with a pair of nicely-cut jeans is quite effective. Also helps to wear something that reflects your personal style, so you'll be comfortable without feeling like you tried to hard. So if you're all about skirts, by all means, wear one!

  • Hawthorne

    SJP Man Hands??? From this pic it looks more like "Alien Hands". Did someone photoshop those suckers to look like a claw from the Creature from the Black Lagoon? Or maybe it's just my eyes playing tricks on me.

  • I'm probably all wrong about this, but it's worked in the past: for after-work dates, I do the jeans + white shirt + sportcoat thing (tweed in the fall, corduroy in the winter, linen in the summer). It draws no attention at the office, and communicates "grown-up" and "not interested in fashion" to the date. I'd rather my clothes not be the topic of conversation.



    Also, my only bit of Queer Eye advice: men, please wear brown shoes with jeans. They look about 1000% better than black shoes.

  • fusskins

    SJP is notorious among my friends for the having "man hands." An unfortunate Vanity Fair layout pointed this out a few years back.

  • Stephen

    Not really on point, but has anyone looked at SJP's right hand in that picture? Looks like something straight out of a zombie movie. Yuck.

  • nancy

    What's with all these recent columns that think they are ushering women into spring by instructing them on how to land a second date? Are there any fashion 'no-nos' for men going on first dates who pine for a second?

  • Often something with lots of stains. No need to set expectations too high. And, for three years, an orange jump-suit, but can't a man put the past behind him?

  • Moges

    Having two older brothers, I know that the average man thinks heels are stupid, because most women can't pull them off and end up walking like they have to go potty and then complain about their aching feet all night.

  • spae

    your favorite pair of jeans and a white button down. this can go for both sexes. simple, clean, and chic!

  • Stephanie, that comment is close-minded. If you are a woman trying to dress to impress on a date, doesn't it make sense to know what a man wants? In my dating years (a long time ago, in a galaxy far far away) I would NEVER ask my buddies how to dress. I would ask my straight girl friends. Duh and duh.



    It goes without saying that people should do what they want, dress how they want, and not fret too much about impressing any one. But, if you are shooting to make an impression on someone, does it not make sense to know the general tast of that someone's demographic?

  • Stephanie

    First and foremost, never take fashion advice from straight men.

  • Brian Van

    It's not about what you wear, it's about taking it all off later. :)

  • Jellyguy

    Awww, Heather, there's nothing I enjoy more than a crimson lip imprint on my shaved skull.

  • Heather

    I have been known to wear a hoodie one too many times. Perhaps that's why i rarely get passed the first date. I have also found that if you really don't like your date and are only going out of sympathy/favor/beer goggles/blind date doubt/desperation, wear red lipstick -- they have no way of kissing you.

  • Obviously tight clothes are the best, especially if they show off your package and/or nipples. You want your date to be thinking about something other than how bad you are at small talk. -F

  • "I'm With Stupid" T-shirts

  • It may not be the most stylish thing, but I've found that body armor is quite pratical to wear on first dates.

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