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Valentine-Proof Your Wardrobe (And Survive The Day Of Hearts)

If there was ever an occasion to clean up for, this is it
by Miguel Escobar | Feb 6, 2017
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The world is burning. Even a cursory glance at the news is enough to tell you that things aren’t going so well for the human race these days. And to make matters even worse, Valentine’s Day is just around the corner, which means that against this backdrop of global turmoil, we’re all going to have to brace for another barrage of seasonal contrivances: teddy bears holding big red hearts, guys on the MRT wearing outrageous amounts of cheap cologne, and wilted roses peddled by the side of the road.

Then of course, for those of us who aren’t wrestling with the crippling loneliness of singlehood, there’s a looming sense of dread: the pressure to arrange something romantic for your girl. She’s expecting a nice date, a suitable gift, or anything else to show how sweet you are, and god help you if you don’t deliver.

So regardless of where you are and what you’re doing on Valentine’s Day, you have more than enough to worry about. Your outfit shouldn’t make matters worse. Take heed of these tips to dressing well on the day of hearts and you might just wake up on February 15 in one piece (or with a woman right next to you).

If you’re single on a night out

First of all, don’t worry too much about it. Sulking about being single on Valentine’s Day (which includes all those sickeningly bitter hugot jokes) is a total style crutch. Keep your chin up and dress yourself in something casual and relaxed, so you don’t look like you’re trying too hard to compensate for your singleness; but still look clean enough to appeal to another lonely heart from across the bar. A nice white button-down shirt, layered up once with a denim jacket, jeans, and white sneakers is a standard outfit, albeit one that makes a good first impression—it’s a healthy balance of cool and smart. But since it’s Valentine’s Day, and we all know that what we wear can have subconscious effects on how attractive we are to the opposite sex, find a way to add some red to your outfit, perhaps with your sneakers, socks, or other accessories.

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If you’re newly coupled-up

We feel you, man. The pressure is on. Valentine’s Day is the ultimate opportunity to impress this new girl you’re seeing, and you’re about to go in, guns blazing. Determination is good, but the trick here is not to get carried away with your need to impress. At this point in the relationship, there’s a tendency for men to show off, often with bold colors or ostentatious clothes (put that goddamn fedora hat away). Be conscious of this and tone down your look. You’re going to want to make her feel at ease with you and the idea of dating you, so still stick to casual, neutral clothes—but of course, never too casual as to make you look sloppy. This is where a nice solid polo shirt comes in handy (maybe one that shows off your figure if you’ve been hitting the gym, because of course you have), tucked into a pair of jeans (no tatters or aggressive washes), or chinos, and smart shoes.


If you’re ready to take the next step

Here’s the man who would really benefit from dressing up. If you have a special night ahead of you—as in, you’re finally going to pop the question (whether it’s coupling up, moving in, or *gulp* marriage)—then by all means, dress to impress. This is going to be a well-documented evening (ie., it’s going to be on Instagram, and maybe even your future wedding video), so it’s important that you bust out a damn good outfit for it. Throw on a sportcoat or a blazer over a button-down shirt—hell, maybe even put on a full suit-and-tie if you’re finally going to ask her to marry you—and go with trousers, not jeans. Make sure to put on a grown-up watch and some grown-up shoes (your Infrareds are going to have to wait). The point is to show her (and yourself, and literally everyone else), that you’re grown-up, that you’re ready for a new stage of your relationship, and that this evening really means something to you, that it’s an occasion that deserves to be celebrated and remembered. So enough kids’ stuff. Dress like an adult, and dress well.

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If you’re celebrating a longtime relationship

And then there’s the rest of us who are already in long, happy relationships, who see February 14 as an opportunity for a simple celebration. We get to be less invested in this than the guy who’s about to get down on one knee, but that doesn’t mean we get to be complacent. No matter how long you guys have been together, she’s still going to expect you to go an extra mile tonight. A solid shirt and a smart jacket (not a hoodie) will do for tonight, with your best jeans (again, NO rips and minimal distressing. It’s Valentine’s Day, for fuck’s sake) and a pair of dressy sneakers will do you just fine.

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