A Valentine's Day Guide To Underwear For Men

A quick Google search will tell you that Valentine’s underwear for men is all kinds of creepy and embarrassing. Buying a pair of pants that have hearts on them (that they’ll continue to wear for seven years anyway) isn’t romantic and it’s definitely not sexy. Even worse, the "funny" guy will buy some sort of ridiculous thong that he’ll come out of the bathroom wearing, only to take off immediately in order to shag you in the missionary position for four whole minutes. If that’s your idea of romance, you really need to sit down and work your way through Matthew McConaughey‘s back catalogue (before he decided to take acting seriously).

Ideally, my perfect man would not take his underwear queues from Justin Bieber’s new ad campaign — and he definitely wouldn’t stuff his Calvins either. Rather, he'd go for something a little more Rocky Horror. A fun game to play on Valentine’s Day is watching how many people are adjusting their boobs in their special sex bra, but it could easily be improved if we got to watch guys poking down bits of lace showing through their t-shirts, too. Unfortunately, the only men’s underwear I could find in lace were expensive pieces of fetishwear, all laughed at hysterically by my roommates. (Secretly, I loved them.)

However, I’m a huge fan of men in women’s underwear — and V-Day is one of the perfect nights to try new things with your better half. It might be a bit weird at first, but remember how much Joey loved it in Friends? But dudes: Just make sure you ask before pulling back your robes to reveal how fabulous your gal's favorite bra looks on you! And if you want to go all out and buy your own ladies' underwear (maybe your partner’s shocking pink doesn’t suit your skin tone and you want a lovely lilac), here’s an easy to understand size conversion chart. Because as with anything, clothes that fit always look better than squeezing into something too small.

Shockingly, not all people are fans of men in women's underwear. Even more shockingly, some people aren’t even fans of the Rocky Horror Picture Show. As easy as it would be to allow these monsters to fend for themselves, I’ve found a selection of suitably stylish pants that aren’t too terrifying and might even be a bit of a turn on.


Topman Berg/Grey Marl Tonal 3 Pack, $25, Topman

I love undies on guys mainly because male butts are so underrated. These underpants will highlight their bum perfectly, though! Boys, you can definitely pull these off, as long as you never ever buy them in white.


Baby Rib Boxer Brief, $16, American Apparel

These classic American Apparel boxers won't distract from the star of the show — your partner's $40 lingerie set!


Calvin Klein 2 Pack Black Trunks, $53, ASOS

Calvin Klein is to men's underwear what Victoria's Secret is to women's underwear — iconic. These black ones are simple, smart and you get another pair to put on afterwards (just in case any mysterious white stains appear on the first ones, obviously).


Diesel 3 Pack Stripe Trunks, $66, ASOS

The red pair in this multi pack is vaguely Valentine's-y without being embarrassing! There's also ample room to make a silly gas pump joke about your junk.


Solid Athletic Trunk, $13, American Eagle

The gold top to these boxers will automatically let any woman know that you are a complete baller. American Eagle also has a buy one, get the next half off deal on their underwear right now! So you can be a totally frugal baller.


Black Spotted Silk Boxers, $30, Debenhams

These understated silk boxers are the most suave item on this list, showing that you made an effort without you actually having to make an effort.


Bold Lace Brazil Brief, $20, BodyAware

For the daring amongst you — lacy panties made specifically to fit your bod! Also available in a variety of colors. (I especially love the gold, of course.)

So, men: Don't worry if you can't work it out, because really, your choice in briefs doesn't matter (as long as they don't stink). Just focus on what's gonna happen when you get them off.

Images: Sohail Fazluddin/Flickr; Getty; Courtesy Brands