The Formula for the Perfect First Date Outfit

Dating is hard--especially when it comes to deciding what to wear. So, we consulted an expert to nail down the formula for the perfect first date outfit. Read on for some very valuable tips.
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Nora Crotty
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Dating is hard--especially when it comes to deciding what to wear. So, we consulted an expert to nail down the formula for the perfect first date outfit. Read on for some very valuable tips.
Photo: iStock

Photo: iStock

Dating is hard. Forget the anxiety that goes into actually getting a date–once you’ve managed to secure one, the real stress begins: Where will we go? What will we talk about? What if I’m annoying? What if he’s rude? What if he hates gerbils? And most importantly: WHAT WILL I WEAR?

We’ve all been there. Just the other day, I was getting ready for one of those elusive first dates. In an absolute scramble, I shook off a few-days-old outfit from the floor and threw it on, only to realize one of the buttons on my blouse was hanging by a thread and the collar was stained with bronzer. Obviously I had to change my direction at the last minute, which only added to the pressure I was already under (albeit pressure enforced entirely upon myself, by myself, but… whatever). Much of which could’ve been avoided if only I’d had a first date outfit game plan.

It makes sense when you think about it: A first date is like the ultimate advertisement. You’re putting yourself out there–but how much should you really be putting out there (if you know what I’m sayin’)? We consulted New York City Dateologist Tracey Steinberg on finding the perfect outfit to help ease your first date jitters.

                                                                              

Photo: iStock

Photo: iStock

Location, Location

For a first date, it can be tough to know how much is too much when it comes to dressing up. Steinberg recommends keeping it safe by sticking to the basics.

"The first thing to do is figure out where you're going, because you really want to dress for the occasion," says Steinberg. "Say you're going to the park: That sounds like jeans and sneakers, as opposed to if he was taking you to a really beautiful restaurant, that would be a silk blouse and heels. So that's the first thing you want to determine. Then, the most important part is you want to wear something that makes you feel confident and beautiful, whether it's your favorite pair of jeans and sneakers at the park, or a silk blouse, a pencil skirt, and heels at a beautiful restaurant."

                      

Your inspo.

Your inspo.

She's a Natural

Personal style is always encouraged--but is it smart to show off your pizza-covered platform shoes and black lipstick the first time out go out with someone, or should you keep it a little more low-key?

"You want to be the best version of yourself," says Steinberg. "I wouldn't say that you should be somebody who you're not, but men in general tend to like a more natural, girl-next-door look--Mary Ann over Ginger from Gilligan's Island... Less is more, as far as your makeup and hair go--you don't want to be too high maintenance. A lot of men can't really identify with a girl who's wearing Gucci, Jimmy Choos, and crazy designer labels head to toe; it may actually turn them off. You want to be the best version of yourself--but above all, you want to be natural."

                               

Olivia Wilde. Photo: Getty

Olivia Wilde. Photo: Getty

What's Trending Now

Every girl loves a trend--but it's wise not to go overboard on a first date. "I'd say, avoid being too trendy--a lot of men don't follow trends, and they won't really know what you're doing," Steinberg advises.

Two trends she recommends ditching for that fateful first meeting? Crop tops and high waisted bottoms. "You want to dress a little bit flirty and a little bit sexy, but you don't want to give away everything. Leave something for his imagination," she explains. "Depending on your age and how confident you are about your body, I would say you want to dress about 25% sexy."

                                 

Miranda Kerr is a first date do. Photo: Getty

Miranda Kerr is a first date do. Photo: Getty

Weigh Your Options

So what is the ultimate first date getup? According to Steinberg, most dates call for a pair of sexy, flattering jeans, heels, and a silk blouse. "I also recommend to my clients that before they even make a date, they have three outfits that make them feel comfortable going for coffee dates, three for drinks, and three for dinner--the drinks outfits being the sexiest and most flirty, coffee outfits, the most casual and comfortable."

More into skirts than skinny jeans? Even better, says Steinberg. "Men really love when women wear skirts and dresses because they are so feminine. Definitely, for dinner and drinks, wear a sundress or skirt if you're into it."

                          

Go complimentary like Zooey Deschanel! Photo: Getty

Go complimentary like Zooey Deschanel! Photo: Getty

Take a Compliment

When you feel confident in how you look, you'll portray that on your date, Steinberg says. "If you feel confident and beautiful, then that's the right outfit for you." And don't discredit your mom's advice, either. "Pay attention to the compliments you're getting from other people. If your friends are always telling you, 'Wow, your blue eyes look great in that shade of blue!'--pay attention to those types of things. Dress based on the clothes that flatter you, and less about the trends or what's expensive. Not too high maintenance, not too trendy, not too much jewelry, not too many designer labels. Just be yourself--pared down in a way that makes you feel confident and beautiful."

Happy first-dating!

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