What to Wear on a First Date

May 8, 2018 by Tiffany Tse

Whether you swiped right or were set up by friends, you’ve just matched with someone who has serious dating potential (hurrah!). And after a butterflies-inducing flurry of back-and-forth messages, you’re finally meeting to see if the chemistry exists in real life. But no matter how many romantic dinners or coffee hangouts you’ve been on, the first date outfit dilemma never quite goes away.

If you’re feeling anxious about what you’re wearing to this initial rendezvous, we’re here to help with a few tried-and-true outfit ideas. After all, there’s enough pressure on dating as it is (Where to go on a first date? What do you talk about? And will you ever escape those dreaded awkward silences?). Let rental take the pressure off. No need to invest in a new outfit. Simply pick out what works for the occasion, wear, love and return.

Below, get inspired by seven ensembles for every kind of tryst, and when all else fails, just remember to wear something that makes you feel comfortable and confident.

1. What to Wear on a First Date to the Movies: Cute, Casual Separates With Major Versatility

JACKET:SPLENDID, TOP: CUPCAKES AND CASHMERE, JEANS: HUDSON

Checking out the latest blockbuster for your first meet-up? Though the two of you will be stuck in a dark theater, you still need something chic. We suggest no-fail, figure-flattering denim. Since you’ll be seated for a couple of hours, avoid low-rise jeans that require constant readjusting and play it safe in a higher-waisted rise. Lightweight layers are a also must for chilly theaters. Make sure whatever you’re wearing underneath is also versatile enough for a night out—we suggest a shoulder-baring style in a trend-driven print like gingham—just in case your cinematic excursion turns into cocktails at a bar ‘round the corner.

2. What to Wear on a First Date to Dinner: Dressy Without Going Over the Top

JACKET: MARISSA WEBB, Dress: Diane von Furstenberg, Earrings: Ettika

The dream classic-but-cool combo? A perfectly fitted leather jacket and a neutral-hued wrap dress with long sleeves. Worn together, these pieces give off the vibe that you’re confident and impossibly put-together—just the message you’re hoping to send with an evening dinner date outfit. A wrap dress doesn’t require heavy accessorizing (otherwise it risks looking overdone), so a pair of modern, two-toned hoops and simple high-heels should do the trick. The resulting elegant, yet approachable look can work for nearly any setting—which is important since dinner dates run the gamut from bistros to Michelin-starred restaurants.

3. What to Wear on a First Date for Drinks: Playfully Polished Pieces That Work for Day or Night

TOP: COOPER & ELLA, SKIRT: CINQ À SEPT, BAG: JASON WU ACCESSORIESAfter-work cocktails call for an office-appropriate outfit that isn’t too stiff or buttoned-up and, at the same time, doesn’t reveal to curious coworkers you’re dressed for a first date. Strike the right balance in professional separates that incorporate a few fun elements—for example, an eye-catching, floral-print shell and a midi skirt featuring contrast pipe trim, ruffles, and an asymmetrical hem. Finish off your look with ankle-strap sandals and a sleek messenger bag —two accents that transition easily from boardroom to the bar.

4. What to Wear on a First Date to Lunch: Trendy & Tasteful But Low-Maintenance

BLOUSE: J.O.A, PANT: M.I.H, EARRINGS: A PEACE TREATY

Somewhere in between the fancy dinner invitation and the informal coffee hang is the pleasant afternoon lunch—where you can have the most fun with your personal style. Since it’s daytime and there’s less pressure to wear something sophisticated or sexy, your lunch date outfit can simply showcase your individuality. Think punchy colors, on-trend shapes, and fashion-forward accessories. Trade in a traditional button-down for a puffed-sleeve blouse, and ditch your regular jeans for wide-leg pants in a sunny hue that’s sure to make your date smile.

5. What to Wear on a First Date to Brunch: Relaxed With a Flirtatious Twist

DRESS: JOIE, CROSSBODY: TORY BURCH ACCESSORIES, RING: STANMORE

Something about the lively, champagne-filled nature of weekend brunches instantly brings to mind pretty florals, pastel shades, and other girlie elements, which is exactly what to channel on a mimosas-and-pancakes date. Opt for an easy-breezy maxi dress that sports a few flirtatious details—such as an off-the-shoulder neckline, a waist-cinching tie, and a cheerful pattern. Since this brunch-going frock (file this under ideal summer date outfits too) is already busy, keep the accompanying accents sleek and understated.

6. What to Wear on a First Date for Coffee: An Effortless Get-Up Infused With Personality

SWEATER: LINE + DOT, SKIRT: JOIE, EARRINGS: KENDRA SCOTT

Coffee date = super low key. Dress for this no-pressure setting in equally laid back separates, like a relaxed knit sweater and jean skirt (nothing exudes a casual vibe more than faded denim). Feel free to add at least one statement piece—like a vibrant pair of earrings—to serve as a conversation-starter over lattes.

7. What to Wear on a First Date with Walking: Chic Comfort With a Hint of Polish

ROMPER: KATE SPAKE NEW YORK, BACKPACK: LOEFFLER RANDALL, SUNGLASSES: ELIZABETH AND JAMES ACCESSORIES

Taking a leisurely stroll with a potential paramour? Without appearing sloppy, aim for comfort above all else. Choose a lightweight romper that allows plenty of room for movement, and add some necessary polish with a hands-free backpack and universally flattering cat-eye shades. Don’t forget a pair of ballet flats or trendy sneakers that won’t pinch, prod or poke your feet as you’re walking and talking the hours away.