How to Dress for Valentine’s Day

Hello and congratulations on having a date for Valentine’s Day—a holiday with more emotional vulnerability, romantic expectations and pressure-to-have-fun baked into it than your birthday and New Year’s Eve combined. Not only do you have to make a reservation somewhere (oops!), find a bouquet that isn’t covered in glitter, and actually get off work in time, you have to look good while doing it. 

But don’t let any of that scare you. Fancy restaurants be damned! You can always just go out for a fancy drink sans reservations, then have DIY-toppings-pizza at home together for dinner. So shake the glitter off your bundle of flowers, tell your boss you have a “doctor’s appointment” and get to it. The only remaining thing to tackle is your clothing. For that, we have some relief in store: We went straight to the big leagues and asked six women who know a thing or two about getting dressed for their Valentine’s Day Date style tips. 

Heed their advice, prepare your chest hair, and try to remember that there’s an 80 percent chance that person on the other end of your affection is going to bring you a stuffed bear or box of chocolates. See? Maybe this holiday is kinda fun, after all. 

The First Rule of Dating is the First Rule of Date-Dressing: Be Yourself

“This advice is super corny but honestly, dress like yourself. For example, my fiance has a uniform of skinny jeans, a gray t-shirt and sneakers that he rocks pretty much daily. He looks (and feels) his most comfortable when he wears a version of this in formal settings—or casual ones. A date is no different. If you dress like a stranger, you’ll ultimately feel like one. Being yourself is the most stylish thing you can do.”

Janell Hickman, Beauty Editor and Brand Consultant 

Your Smile is Your Best Accessory. So is Your Scent. So Are Your Literal Accessories

“This should be obvious but sometimes you never know: take a shower and wear your favorite cologne, but don’t overdo it. It should be a signature scent. My husband always smelled the same when we first met, and I love the smell of amber now.

I love an untucked button-down jeans and brogues or chelsea boots with jeans—pretty classic. Don´t wear a lot of jewelry, maybe one leather bracelet from Dezso or Miansai would be cool. Send flowers ahead of time to home or office. Don´t keep her/him waiting, be on time. Smile!”

Karla Martínez de Salas, Editor in Chief, Vogue Mexico and Latin America

Make ‘Em Weak-in-the-Knees By Showing Off Your Ankles

“Navy sweater with a crew neck collar—ideally a regular weave, though I think a cable knit is fine if you have no choice—with a white t-shirt, also crew neck, peeking out ever so slightly from above the crew neck of your sweater (you’ll want to make sure the collar on your sweater is a little wider than the one on your t-shirt) and then! add a pair of black jeans, preferably straight-to-skinny leg, not too skinny and definitely not white. They shouldn’t be cropped, but they shouldn’t be baggy either. Ask them to flirt with the lower half on your ankle bones, that should do it, and if you have brown suede sneaker boots, wear those. If you don’t, do you have any brown suede shoes?”

Leandra Medine Cohen, Founder, Man Repeller

Try a Turtleneck and Give New Meaning to the Term “Necking”

I don’t see menswear and womenswear separately. Actually, I find myself talking most of my own styling cues from menswear. Right now, I’m into suiting with a matching turtleneck (which is manifesting design-wise with my brand of womenswear, Henning—shameless plug). I think it’s a great way to look classic and cool—the perfect Valentine’s day vibe for women or men, in my opinion!”

Lauren Chan, Founder and CEO, Henning

You Don’t Have to Wear a Suit to Dress Up, You Know

“When it comes to a big date, less is more. A formal suit and tie winds up feeling too stuffy, even for a fancy Michelin-starred restaurant. I love the idea of layering a crisp t-shirt or thin cashmere shirt under a blazer. It’s still dressed up but more deliberate – like you styled it on purpose, which…you did. You can be a minimalist and do shades of black, white, and gray, or you can make it more daring by throwing in an unexpected color like kelly green or buttery yellow. It’s a modern take on date night that involves nearly no effort but has a big payoff.”

Diana Tsui, Editorial Director of Medmen, Stylist

Do a Button-Down to Get Down

“Do you know what I like? I’ll say it. CHEST HAIR! My husband has the most beautiful rug on his chest and I love that he lets me dress him in button-downs. He doesn’t protest when I have him unbutton the first three buttons, either. Yowza!”

Katie Sturino, Founder of Megababe, Body Positive Advocate

So there you have it. No matter what you wear, be it turtleneck or khaki pants–or both, assuming you’re going to a restaurant with a shirt-AND-pant policy–just remember that there’s a person who’s showing up tonight to see you, not your outfit. Deep breath; you look great; you got this!

Amelia Diamond is a writer and creative consultant living in New York City. Follow her on Instagram here.