A guy once told me that he never thinks much about his underwear (or back hair for that matter) before a big date, because once he gets to the point of standing in his skivvies with a girl, he's reached end game.
Newsflash: unless your score is drunk as a skunk, she's still judging you at the eleventh hour. And don't you want her coming back for more?
I sat down with resident expert and underwear designer Jake Joseph—founder of Jake Joseph Co.—and my frisky sis, Sister Pen, for a candid talk about this often forgotten wardrobe essential. In particular, I wanted to discuss how to dress for those moments between standing in nothing but your boxers and taking it all off for the (hopefully) big night with your lady.
Get Rid of Girl Repellent
Depending on what you're wearing, your lady will either assume that you're game for a roll in the sack or having an asexual reproduction day. Case-in-point, Sister Pen recalls: "One of my boyfriends had a pair of underwear in his rotation from a time when he was a fat kid. It wasn't just old and falling off him, but it had a really big hole in the ass, too."
You wouldn't wear a poorly fitted, frayed suit to a job interview, right? Same goes for your underwear on nights when you are hoping to get it on. Fortunately, if done the right way, your underwear can broadcast your desire rather than dampen the mood.
Sister Pen says, "Another ex of mine had this owl underwear. He knew it was my favorite so every single time he wore them I knew he wanted to have sex. It was a very clear signal."
Enforce Quality Control
I'm all for lucky underwear, but when it comes to impressing your girl, that luck runs out once the "lucky" pair gets so ratty that it looks like you've been attacked by wolves. You may very well fantasize about having your underwear ripped clean off your ass, but please don't start the job for us with a pair of holey, washed-out skivvies. Same goes for underwear with stains on them or stretched out elastic.
"At the end of the day, when you're naked, that's all you have," says Joseph, "but the view in the moments preceding total nudity is important, too. What you're donning on the outside shows how well you take care of what's inside that underwear you're wearing."
Lose the Funny Stuff
Whether you got them at Christmas from your Uncle Joey or picked them up as part of a raunchy Halloween costume, I know that you have a few ugly or weird pairs that get thrown into the rotation long after laundry day has come and gone. By that point, it's either the one of those or yesterday's pair worn inside out. If you must, I say go with inside-out over ugly.
Sister Pen recalls being shocked into the next millennium by an offensive pair of bright green, neon boxer briefs. "He said, 'My mom bought them for me and these are the last pair I have to wear.'" Sister Pen's response to his "lame ass" excuse? "Do your laundry!"
Joseph understands that laundry does fall by the way-side from time to time. His easy fix: "Throw more underwear into the rotation. It won't kill you to buy a few more!"
Consider The Material
Underwear rubs up against you all day, and eventually your girl will be rubbing up against your underwear, too, so make sure that you check out what your skivvies are made of. Joseph's rule of thumb: "If the material would look good on you as a shirt, it would make a good pair of boxers."
Not only should the cloth your underwear is cut from look and feel good, but it should hold up after a few washes, too. For example, Jake Joseph Co.'s high-end boxer briefs are made of a soft, durable bamboo. But you don't have to break the bank to find quality underwear. Jockey's classic 100% cotton underwear, for example, are a low-cost alternative with a respectable lifespan. Be sure to check out underwear in that yummy, light, and skin-hugging micro modal material, too.
Ditch the Tighty Whities
Tighty whities are to men as granny panties are to ladies. According to Urban Dictionary, "The pros of tighty whities are support in gym class and hiding an erection." The cons? Penis strangulation.
Dear God, please stop strangling your penis (and the female sex drive)! You have so many humane alternatives; boxer briefs, boxers, low-rise trunks. And before you go on about how they aren't actually white, variations on the theme won't work, either. Truth be told, it isn't the color so much as the cut that make them so offensive. They make you look like a baby.
These days, it seems even high-end brands are offering skivvies with their names written in huge script across the waist. Very eye-catching, but when the label competes with the size of your junk, our minds can't help wandering from sex to our next shopping spree. Show some real class and taste. Don't make your underwear into a billboard.
Avoid Being Flamboyant
Some of the underwear on offer these days can be too out there for even my most flamboyant friends on Gay Pride Parade Day. So if you're trying to up your game with the ladies, steer clear of underwear with bling, backless underwear, or—need I say it—the dreaded thong. If you're underwear looks more like a jock strap, then all is not well in paradise.