You’ve ordered the gift and made a plan, your apartment has at least one nice candle: you’re ready for Valentine’s Day. Now it’s you time. Specifically, it’s time to figure out what you’re going to wear on this date. Because looking good is important! And let’s face it: it’s also a exceptionally good excuse to take advantage of the end-of-winter sales that are raging right now. Of course, what you buy for your February 14th flex will depend on what kind of date you’re planning (just double checking: you made a plan, right?). Luckily, these six stylish, coupled-up guys are here to show you how to put the lit in candlelit (sorry) and the cop in copulate (sorry), whether it’s your first date or your 100th one.
First Date: On-Theme Athleisure
Whether it was your choice to go on a first date on Valentine’s Day or you got roped into it by an outside party, the fact that you’re meeting someone for the first time on such a high-stakes romantic night is somewhat ridiculous, but also kind of fun, and you should show that with your attire. Make Kelly Oubre Jr. your spirit animal by wearing luxed up athleisure gear in a palette of red and black.
Date #3 is a good time to conjure the style energy of a guy like Rami Malek, who is confident but cool in everything he does—including picking out shirts. Go for a knit polo or one of those swanky camp-collar joints and a pair of nice black trousers and you’ll feel like a million bucks through every stage of what promises to be a mercilessly long, but hopefully also enjoyable, date. When you get to date number four on February 22nd, you have our permission to circle back to Kelly Oubre Jr terrain and just go to the damn movies. You earned it.
If you’re braving the Valentine’s Day crowds and shelling out extra cash for the same dinner you could have tomorrow night even though you’ve been with your partner for months, or even years? You, sir, are a relationship badass and you should dress like one in head-to-toe black. Yes, all-black is also something you wear to funerals, but if you do it like The Weeknd, it won’t feel creepy and ominous. That is, more military than formal, more Jeanne-Claude van Damme than Jay Gatsby. This also doubles as an excuse to buy yourself those expensive boots—assuming you encourage your partner in life and retail to do the same thing.
It’s rare that Valentine’s Day plans reach Hallmark-movie levels of formality, but it happens. Maybe you’re popping the question in some extravagant way or attending the wedding of someone who did. Or maybe you just have fancy friends. Whatever the case, if the night calls for getting massively dressed up, Google every image of John Legend on the red carpet and you’ll have what you need to succeed. The guy always looks sharp and has a habit of going 10% swankier than he’s required to—and 10% swankier is the key to nailing V-Day Formal. Consider velvet loafers, or a double-breasted suit. Maybe add some jewelry to your look. If it makes you feel a little bit like a prince, you’re doing it right.
If your date involves surprising your beloved with a quick weekend escape to a warm locale, it doesn’t matter what the heck you wear because you just won Valentine’s Day. But, since we’re talking about it, and since you deserve to buy yourself something nice for making such a extremely dope plan, we advise you to conjure the joyful, Instagrammable energy of Zachary Quinto and Miles McMillan and buy yourself a vacation-friendly accessory. Big sunglasses, a new hat, whatever will make the weekend even more stylish and even more relaxed.
If you made it to the end of this article and don’t have plans on Valentine’s Day, you deserve what we’re about to give you: permission to wear sweats on the most try-hard day of the year. On the top. On the bottom. Unlimited fleece for two. There is just one request we’ll make, and that’s to put some effort into what’s underneath the sweats. If you’re Justin Bieber, that’s a thousand tattoos. If you’re a normal person, that’s new underwear and a chain necklace.