Date Night Looks That Never Fail (or Ghost) You
Love is in the air. Reservations are confirmed. What's the look?
It’s a tale as old as time. Guy meets girl. Guy asks girl out. Girl says yes, but has nothing to wear. Suddenly, what starts as a matter of the heart quickly becomes a crucial decision-making process.
The key to a perfect date night outfit is balance. Try not to overthink it (we know, easier said than done). Start with a piece you can rely on—your favorite pair of shoes, the pants that fit just right—and build your look from there. And like any recipe, it all comes down to the best ingredients.
Much like a blind date, the look can go in a few different directions. Factors like weather, location, and itinerary must all be considered, especially here in New York. Madison Avenue and Madison Square Garden call for two very different aesthetics. There’s also knowing your audience—is this date your soulmate, a situationship, or the Galentine’s crew? Outfits will vary.
By the way, this guide applies to platonic date nights, too. Full transparency: this editor of Theory is chronically single and a firm believer in V-Day girls’ nights.
In theory, you should always have three go-to date night options. Here’s what we suggest:
1. The LBD
Never rule out the little black dress. It’s your Audrey Hepburn-meets-Carrie Bradshaw moment. Dress it up with pointed-toe pumps and a bold, mob-wife-coded coat. If you want a little edge, wear a tall boot with a leather jacket. It’s your love story. Be the main character.
2. Matching Sets
Here we have a pre-fixe menu for date night dressing. Matching separates do the work for you. They can read casual, tailored, or even formal. A satin top and skirt. Coordinated knits. Suiting, sans underpinning. The limit truly does not exist. A guaranteed win. Game, set, match.
3. Jeans Are Allowed
Denim is your friend that sometimes flirts for fun. Skinny jeans can be slimming, but don’t sleep on a flared, wide-leg cut. That basketball game you don’t remember agreeing to? Pair it with a fitted tee and sneakers. For a swanky dinner downtown, do an oversized blazer (perhaps with a brooch for some razzle dazzle), then swap sneakers for a sleek stiletto. Whatever you do, don’t break up with your denim.
PS: Where to Fall in Love in NYC
If you’re lacking inspiration this year or just not feeling the love, here’s where the city becomes a scenic, romantic companion:
The Park: The city’s full of them. If you’re braving the current cold front for a casual stroll, you’re bound to see couples holding hands through their cozy mittens. All the feels. (e.g. Central Park, Washington Square Park, Prospect Park)
The Bookstore: Turn the page on your dating life. Sometimes the most intimate moments come from good literature. (e.g. The Strand, Three Lives & Company, Books Are Magic)
The Jazz Bar: Catch a vibe. Set the mood. Let the sultry music and soothing ambience comfort you. Highly recommend for a solo date. (e.g. Smalls, Django, Tomi)
Whether it’s a first date with a secret admirer, an exclusive evening with your longtime partner, or a Wuthering Heights watch party with no boys allowed, remember to love yourself first.
And, of course, what you’re wearing.