Whether you’ve swiped, Skyped or been set up by friends, first dates are nerve-wracking on many levels. (Will he look remotely like that awesome Bumble photo? What if that Emma Stone clone is an ax murderer?) What you wear to coffee, cocktails or dinner at that hot new restaurant shouldn’t add to your stress. As stylists and pro shoppers for DC Style Factory, we prep clients for many events where a first impression is paramount: job interviews, weddings and, yep, first dates. Here are our do’s and don’ts for how to look good when looking for love.

1. Your outfit on a first date should fit the occasion — casual for coffee, more dressed-up if you’re doing dinner after work. The idea is to convey confidence and polish via your garments. For example, our model, graphic designer and Instagrammer Alex Rice, below, is wearing leather-panel leggings and an oversize cardigan for a weekend java meetup. The leather detail in her leggings plus the pointy-toe style of her ankle boots dress up her look while the comfy, cozy sweater ground it, making for a daytime date look that says: “I made an effort … effortlessly.”

Most of Rice’s clothing in these photos comes from Violet Boutique in Washington’s Adams Morgan neighborhood. The heels and booties are from Sam Edelman, which you can find at Bloomingdale’s.

(Photo by Emma McAlary)
(Photo by Emma McAlary)

2. Pay attention to what’s on your feet. You want to, er, walk a fine line between comfortable and slightly sexy. That means a hip bootie or a mid-heel pump that says “I’m fun and approachable,” not a sky-high stiletto that screams Kardashian or, even worse, may result in an injury. Before she was a stylist, Rosana sprained an ankle trying to wear platform pumps on a dinner out with a very tall date. Learn from our mistakes!

Unless you’re meeting a new potential boyfriend or girlfriend for a hike, leave the sensible shoes at home. (We’re looking at you, L.L. Bean boots or Birkenstock anything.) You want to be a little dressy, a little cool.

[My OkCupid profile was so bad my now-fiancee ignored me. Then I learned how to dress.]

3. We’re fans of what we call the icebreaker accessory — a piece that’ll give you something to talk about if the conversation stalls, such as Rice’s necklace in the above photo. That might be your Mom’s vintage bracelet or a pair of shoes you bought in Paris — anything your date might notice and or that you might have a story about.  On Jenn’s first date with her husband, she carried a funky, custom-painted velvet bag he still remembers.

4. For an after-work drink, it’s best to work with transitional pieces. These are wardrobe staples that move easily from the office to after-work dinner or drinks. Instead of work trousers, we paired a blazer and high-neck blouse with skinny jeans on Rice, transforming office-appropriate attire into off-duty style perfect for a weeknight first date.

(Photo by Emma McAlary)
(Photo by Emma McAlary)

5. If your first date is on the weekend, don’t be afraid to vamp it up a bit. Whatever you do, though, don’t flash a ton of skin. (Step away from the crop top, honey.) Anything that’s overly come-hither suggests a hookup, not getting to know each other. Unless, of course, that’s what you’re trying to do, but that’s not why we’re here. The ideal first-date outfit dances between a little sultry and a little chic. So yes, you can wear a short skirt, but balance it with a draped blouse, boyfriend blazer or an oversize sweater like the one Rice is wearing below. If your top is a little low cut, pair it with a scarf or layer it under a cardigan.

(Photo by Emma McAlary)
(Photo by Emma McAlary)

6. Whatever you wear, dress like yourself. If you’re a Southern, preppy gal with a penchant for sundresses, don’t wear a Miley Cyrus-style sequined jumpsuit. If you’re an artsy/free-spirited person, let that come through via accessories. Just don’t go overboard; if you’re a rocker chick, that would mean wearing your leather jacket or your motorcycle boots or leather leggings, but not all three together.

We tell our clients: What you wear sends a message. Wear clothing that speaks about you, not for you. And who knows — the right outfit might result in a great match.

 

READ MORE:

My ex-husband’s mom is still my mother-in-law

On a third date, she said: ‘You can’t afford me, Trotsky’

5 lines that will out you as a snob on a first date