Ask Natty: What Should I Wear On A First Date?

by Natalie Decleve · April 19, 2011

    ASK NATTY: First Date Fashion

    Dear Natty –

    I’ve just managed to get my longtime office crush to ask me out (yay!) but now I realize that I have NO idea what to wear (yikes!) We see each other almost every day, but this will be the first time that he’ll see me in something other than “business casual” and I really want to get it right. Can you help me?!

    Non-Business Casual

    Dear NBC-

    Ah the illusive “perfect-first-date-outfit.” No matter how confident you are, deciding on what to wear for the all-important First Date always requires extra attention. Here are the DO’s and DON’Ts for choosing a look that’ll have him begging for a second date…

    DON’T try to make a statement with something uber trendy. Trust me, guys don’t care if turbans are super chic, that mixing crazy, loud prints is THE thing or that furry Mongolian vests are like, totally a wardrobe staple. If it makes you look like the victim of a wookie attack, or just a fashion victim – you’ll likely find yourself the victim of the dreaded “I’ll call you”. The Man Repeller has some hilarious examples of wardrobe birth control.

    First Date no-nos

    Balmain chain dress $3,654 -

    Erin Fetherston long sleeve top $119 -

    Alexander McQueen one button blazer 525 GBP -

    Thakoon cropped fur vest $895 -

    Giuseppe Zanotti heeled sandal $775 -

    Mesh jewelry $170 -

    Terror Eyes Cosmetic Contact Lenses - Magic Brown Eye- Buy Jewellery $19 -


    DO dress like a girl, if you are one. That doesn’t mean you have to wear a skirt or a dress, but straight guys are pretty simple. While they may not understand fashion (see above), they do know what they find attractive; and it’s not shoulder pads or collars buttoned up to the neck. So dress for your body type: Got great legs? Show ‘em off. An hour-glass figure? Wear something nipped at the waist! Beautiful eyes? Choose a color that compliments them. Sometimes the sexiest bit of skin is as simple as your collarbone, shoulders or wrists.

    DO keep ‘em guessing. While I’m all for flaunting it if “you got it” – you also don’t want to give away the milk for free. Think “flirty” not “slutty” when choosing your first date outfit. Leaving a little to the imagination will leave him wanting more…

    First Date Yes

    L Agence waist dress $348 -

    Haute hippie dress $165 -

    Sleeveless top 45 GBP -

    Balenciaga scoop neck tank 365 GBP -

    Theory skinny leg jeans 189 EUR -

    Christopher Kane leather sandal $595 -

    TopShop leather heels $145 -

    Hammered gold earring $68 -


    DON’T overdress. Nothing is less attractive than someone who’s trying too hard, whether it’s to be funny, smart, or well dressed. The goal is to appear effortlessly chic and pulled together. So, no cocktail dresses, “evening” shoes or too much makeup. Think dressy fabrics in casual styles, denim and heels and chic accessories.

    And above all …

    DO wear something that makes YOU feel confident. Just like with everything else on a first date, you want to make a good impression – but one that represents who you really are. Dressing like a sexed up vixen when you’re really more of a hipster will not only make you uncomfortable, it’s pretending to be someone you’re not. And there’s no point in luring a dude with the ol’ bait and switch, it’ll just lead to issues down the road.

    Now good luck, and do report back to let me know how it goes!