Back when you were a kid, Valentine’s Day was all about dropping a hint about your feelings to your crush in the form of a Candygram or rose in the hopes that she’d hold your hand during recess.

Flash forward to adulthood, and if you’ve got a crush who hasn’t been picking up on the hints you’ve been floating her way — the dinner and drink invitations, the resting-your-hand-on-her-the-lower-back stunts, the wink-y face emoticons you’ve included in texts — it might be time to do something more drastic.

But if you’re going to spend Valentine’s Day trying to get your love interest out on a date, into your bed, or even to give forgive you for something dumb you did, don’t go TOO DRAMATIC. Just stick with sending her something nice like a box of chocolates or something funny like a framed and signed picture of yourself for her bedside.

And whatever you do, don’t pull the ’80s movie cliché of standing outside her home holding a bombox over your head or spilling your feelings to her while wearing one of these 8 outfits.

The Classic Heart Costume


You’d think that professing your love while dressed as a big heart would be a safe, easily-understandable play. But really it’ll just make you look like you’re one of those guys dressed like a Subway sandwich begging passersby to try his “$5 footlong”.


valentines day outfits for men

If your crush has a thing for grown men dressed like little babies with wings and bow-and-arrows, she probably shouldn’t be your crush.

Stripper Cop


If you dress like a sexy cop to surprise her, the obvious reaction before she recognizes you will be “Oh shit, I’m getting arrested” and then her mind will troll through all the laws she’s broken recently. That’s not the mindstate you want want a woman to be in right before you tell her your feelings and/or try to seduce her with what will probably be terrible stripper grinding.

2Pac in a Bathtub


Maybe you’ve found out that your crush is a big 2Pac fan. So if you’re going to lure her back to your apartment so that you can surprise her in your best 2Pac get up while reclining in the tub… don’t, because that’s the scariest thing in the world.

Terry Richardson

valentines day outfits for men

Perhaps you’d like to spend Valentine’s Day taking sexy snaps of your crush Terry Richardson-style. Odds are though, that she’s going to know Richardson more for the accusations of model abuse that have been leveled against him than his “artsy” pictures of Miley Cyrus. Don’t creep her out.

Channing Tatum in Magic Mike

Magic Mike

Simply put, you’re not going to pull off the Chippendales look like Channing Tatum. He’s an ex-stripper and current professional actor. You’re not. You’re going to look like a fool.

Captain of Team 69


The fact that this exists is simply insane. Again, if your crush is into this, you shouldn’t be into her.

Whatever This Is

valentines day outfits for men

Actually, for this… just go for it. If your crush likes you while you’re wearing plush boobs and butt, that’s love and you two are meant to be together.


SlamXGarb: The 8 Worst Valentines Day Outfits For Men