Style Guides

What to Wear on Valentine’s Day: The Express Men’s Guide

What to Wear on Valentine’s Day: The Express Men’s Guide

There are two ways to play the whole Valentine’s Day thing. Option 1: Avoid thinking about it until February 13th and spend 24 hours in dry-cleaner-begging, reservation-making, bodega-flower-buying hell. Option 2: Embrace the opportunity to buy some new clothes, eat some delicious food, and spend some QT in the bedroom with someone you’re into and start prepping now. No contest, right?

Assuming you’re with us on this one and agree that Valentine’s Day is a great excuse to make February suck less, let’s talk about what you’re going to wear on the big night. For starters, as much as we appreciate color in a man’s wardrobe, even we can admit that red, pink, or purple looks on Valentine’s Day can feel a little on the nose. Our recommendation: try black and brown instead. Black is slick and cool, brown is cozy and inviting. Together they’re the wardrobe equivalent of the perfect date and—huge bonus—the building blocks your wardrobe needs right now and in three months when it starts to warm up.

Here, a stylish black-and-brown look for whatever you’ve got brewing on V-day. Now all you need to do is figure out exactly what that is.



For the fancy, romantic dinner . . . and drinks . . . and . . .

Even if you aren’t going to a posh, white-tablecloth restaurant for Valentine’s Day, we encourage you to wear a suit for your dinner date. It’s a timeless gesture that still counts for a lot, just like that bouquet you’ll be holding at your date’s door.

A black, slim-cut suit is the coolest route to go here, especially if you keep the accessories equally slick. A black leather belt and Chelsea boots have just the right kind of city flavor. A chocolate brown dress shirt, meanwhile, is the style risk that takes this look to the next level. Wear the shirt without a tie for a minimalist, modern feel. Remember, you’re going for smooth, not stuffy.

What’s underneath: Our boxer briefs create a smooth look under a suit—and look smooth when that’s all you’re left wearing, too. Keep it classy with solid black.



For the low-key date, blind date, group hang, and everything in between

Maybe you’re not even sure if your date is technically a date. Or maybe you’re heading out to party with the Lonely Hearts Club. When you want to tone down the Meet Joe Black vibe, swap your black suit out for its badass brother: black jeans. Our 4-way stretch denim creates a clean, modern look while allowing you to dance, dine, and flirt the night away in comfort.

On top, you can’t go wrong with a Henley in black or brown. This simple shirt makes you look like you’ve been working hard at the gym, even if you’re less than religious about going. Throw a suede or leather moto jacket on top and you’re really cooking with gas. Our chocolate brown version even has a removable Sherpa collar for extra swagger—and warmth. Finish the look with your trusty Chelsea boots and you’re ready for anything.

What’s underneath: Our sport trunks are perfect for stretchy, slim-cut jeans because they won’t show through. Bonus points if you’ve been doing your squats and can rock the ultra-short length with confidence in the bedroom.



For the romantic night in—takeout, a movie, the whole nine yards

Planning to skip the fancy prix fixe meals and overpriced cocktail specials and skip right to the viewing portion of the evening? Congrats! Getting dressed just got way easier. Sweats are an option, but since this is a special occasion, we like the idea of some roomy chinos and a crew neck tee for a slightly more polished spin on couch attire. In brown and black the combo looks smooth without sacrificing comfort. Finish the look with simple white kicks you can easily kick off, and that “I just took a shower” scent (the secret: body wash) and you’re primed for a close encounter. Just don’t forget the flowers!

What’s underneath: Instead of playing it too-cool-for-school, this is a good moment to let your funny flag fly. Heart-print boxers? Sure, why not?