A Brief Guide to Buying Men's Underwear

Illustrations by Naomi Otsu

It's a question as old as time, and while the answer differs man-to-man, there's a good reason why some guys opt for boxers, and others opt for briefs. Boxers are great if you're willing to exchange support for a more relaxed fit. If you find that you're in need of more leg movement from your underwear, then boxers are your ticket. While you may suffer from wedgies with boxers' looser fit, you can always try to buy a pair of shorts without a center back hem. These are called "three panel backs" and use extra seams to prevent bunching and distribute the fabric across the back end. If you are someone who wants the best of both worlds, there is always the tried and true option, boxers briefs, which provide the perfect mix of comfort and support. We aren’t necessarily suggesting you run to the store and buy pairs of each style to give them each a test drive. But finding the right fit for you will do wonders.

White shows stains easier than darker colors. While tighty whities are as much apart of men's wardrobes as any kind of underwear, you're really better off keeping your bottoms black or blue. Not saying you're having any accidents, but to be fair, dark shades will hide any issues you may run into.

If you consider underwear to include undershirts, then you're undershirts are what you want on the lighter side of the grey scale. While you may think that this will show sweat easier (and sadly, it most certainly will), if the function of an undershirt is to sit…well, under a shirt, then you want something that isn't going to be seen through your outer layer. White will smooth out your appearance and, if buying a v-neck, won't be seen under your buttondown shirt either. If tank tops are your thing, may we suggest these “wife pleasers” by Uniqlo. They’re a bit pricer than the tried and true pack from Hanes, but the differenc in quality is noticeable enough that we don’t mind shelling out a few extra dollars. As far as any undershirt stains, well, there's a reason they tell you to recycle your white tees after a couple months.

Let's start at the top…or rather, at the bottom. A lot of things are going to be affected by how you size your drawers and a majority of your underwear problems are going to arise when you're rocking a size too big or too small.

Are the bands at the base of your legs too constricting? That's a clear indication that you need to size up. Are you tucking your underpants into your pants? You're probably a size too big. If there's one thing on your body that should fit you like a glove, it's your underwear.

If you're caught between sizes, determine where your sizing issues actually are. If the legs are too big, then size down. With waistbands made of elastic, a tight waistband on the first few wears will go away after the elastic stretches out. Feeling pinched in more ways than one? Size up. You already know that things shrink in the water, so even with an oversized wear, the size will shrink-to-fit after a run in the washing machine.

How long your underwear lasts is really up to you. While the ball(s) are in your court, you're better off clearing the bench no later than twice a year, and that's assuming you have more than seven pairs on deck. Considering it's something that you're wearing on a regular basis, you're looking to have multiples on multiples. The sign to throw them in the trash bin instead of the laundry bin? Fading, over-stretching, and the obvious, irremovable stain are key signs you're better off copping a new three-pack.

While it's a lot easier to just throw your undewrwear into the wash with the rest of your gear on laundry day, you should know that even your delicates deserve delicate treatment when it comes to the wash and dry cycles. There are two things that really ruin your underwear: a hot dryer, and fabric softener. While the issues with a hot dryer are obvious, there's no denying that anything above warm will fade out fabric, and destroy the elastic in your underwear. If you're smelling burning rubber as you open the dryer door, then you know you're going too hot.

The issue with fabric softener may not be as obvious. While fabric softeners make your cotton clothes smooth and soft, they wreak havoc on your underwear. Considering most underwear is built with microfiber fabrics, or even the simpler blended fabrics, adding fabric softener is a step that will wear out the overall shape of your underwear, and leave residues behind.

The solution? If possible, wash in cold water with detergent only. Yes, it involves you sorting out your underwear and adding an extra step at the laundromat, but if they fit like a glove when they went into the wash, this is how to make sure they still fit that way when they come out.

When you're lifting, your lower half needs lifting too. While you're probably not packing a different pair of underwear in your gym bag, you're going to be better off. Aside from preventing pulled muscles, your extra movement will result in chaffing and pain if not handled properly. Cotton is the obvious choice for a breathable, functional fabric, but you're better going with something more moisture wicking, especially when gym priorities are about preventing foul smells with layers that support you. If guys wear wrist guards and weight lifting belts, consider this in the same family—just on a smaller scale.

Hand-me-downs are one thing, but if you're buying your underwear used, then this list (or any advice on this website) isn't for you.

In a world where Hanes and H&M make underwear, it certainly isn't necessary to be dropping major dough on your underwear. A Hanes five-pack costs under $30, and that's really all you're going to need. If Hanes isn't your brand, or you just want to upgrade your unseen style, you can never go wrong with some Calvins. They'll all run you more than your traditional three-pack, but you can expect more intricate and secure sewing—along with a more diverse fabric selection. In case you haven’t been underwear shopping recently (hopefully, you have though), take a trip to you nearest Target or Macy’s to get an idea of just how many options are out there. Brands like Hanes even sell packs with extra pairs included to really give you that extra bang for your buck. There’s nothing wrong with having more underwear in the drawer. 

Sure, it's easy to just stick to the classics and go buy a pack of Hanes or Calvin Kleins from your local department store, but maybe you feel like repping your favorite brand down to the underwear sometimes. Are they any different? No. But admit it. Sometimes you can't help but fall for the logo. 

There are plenty of options on the market these days. The most obvious is probably Supreme's special edition Hanes boxers remixed with a Supreme logo waist band. Cactus Plant Flea Market's own boxer briefs also pop up on their web store from time to time, but are a little harder to get your hands on than Supreme's aforementioned pairs that stay stocked year round these days. If you're really committed to some unique streetwear-branded underwear, Kith offers a customization station at its SoHo flagship now where you can mix and match your own personalized three-pack of Kith x Calvin Klein co-branded underwear. Even Rihanna's Savage X Fenty just introduced its own men's line. You have got options if you're tired of the same old same old.