Underwear 101

We've put together some of the basics about men's underwear. After all, we are the experts.

Underwear 101

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Almost everyone wears it, it’s a particularly intimate part of our everyday lives, yet we nearly never talk about it. (Well, we do, but that’s kind of our thing.) You guessed it: underwear. Underwear flies under the radar in quite a few discussions about men’s style, but not for lack of staying power in your wardrobe. More often than not, it’s the first thing you put on and the last thing you take off. . But, what kind of underwear should be in your closet? What are your options, and what’s right for you? How often should you change out your wardrobe? And, how often should you change your underwear, for that matter?

Guys, we’ve got you covered literally and figuratively. Here’s what you need to know about the underwear basics, from the waistband down and the ground up. 

Why Wear Underwear?

To begin with, it’s important to understand why we wear underwear in the first place. While it’s certainly possible to freeball wherever you go, it’s not the safest or healthiest option for you or your clothes.

Not wearing underwear means that your junk is in direct contact with your clothes all day long. This can be a problem, as we don’t tend to wash our pants nearly as much as we wash our underwear. Re-wearing that same pair of sweatpants again means you’re wearing your sweat again, too. Dirty clothing can leave you exposed to germs, bacteria, and other contaminants that can cause nasty and uncomfortable infections over time. Beyond that, with no barrier between your manhood and your pants, it’s entirely possible to make stains in embarrassing places. 

Taken from another perspective, it’s not always safe to go commando. Take going to the gym, for example. Apart from giving everyone around you a free show they’ll never forget, not wearing underwear can mean that your bits are moving around quite a bit more during your workout. That can lead to painful crushing, squishing, or twisting incidents that can cause permanent damage. Outside of the gym, going commando under any pair of pants with a zipper at the crotch means an immediate threat to your manhood.  

If none of that concerns you and it probably should, let’s be real then it might be worth mentioning that not wearing underwear can be quite uncomfortable. Underwear is designed to support and protect you as well as provide some necessary warmth and comfort in terms of fabric. Essentially no pair of pants is going to give you the support you need down there, and we’re firm believers that you’ve gotta treat the boys right.

Convinced? Let’s talk about building and maintaining your underwear wardrobe.

Building Your Underwear Collection

Let’s assume you’re starting your underwear collection completely from scratch. Maybe you’ve never owned a pair in your life and you’ve been rocking that “natural” style until now; maybe you tragically lost your collection in an airplane luggage mishap. What’s a boy to do? 

Start out by  selecting some basic pieces to fill out your everyday wardrobe. When it comes to the pieces themselves, you’ll need to consider material, cut, and color.

Material Options

One of your first considerations is what kind of material you’re interested in wearing. There’s a wide range of options on the market, so let’s look at the most popular ones and why you might want ‘em. 

  • Cotton is natural, breathable, easy-to-wash, and a long-lasting material. It’s highly recommended as your everyday choice for these reasons.
  • Linen is another natural material that lasts quite a long time, but can have a rougher texture than cotton. Still, it’s another good everyday option.
  • Cotton blends are breathable, but more flexible than straight cotton. Usually, that flexibility is thanks to the inclusion of some kind of elastic material, like nylon or spandex. Cotton blends are preferable for tighter options like briefs and trunks, especially if you’re planning to wear them while working out or otherwise in motion.
  • Synthetic materials like polyamide and elastane are great for give and stretch, but tend to be less breathable and long-lasting than natural options. You might opt for synthetics for pieces you don’t wear as often as every day, but would wear for special occasions.
  • Silk is an extremely soft, luxurious, and relatively breathable material. It’s also difficult to wash and maintain, but so are many of the finer things in life. Still, it’s probably best to reserve silk for special-occasion pieces.

Style Options

When it comes to style, your two key considerations are cut and color.  

Cut mostly comes down to personal preference, but here are some tips: 

  • Styles that are cut at the top of the leg, like briefs, tend to bunch less under casual clothing (like jeans) than longer styles like boxers and boxer briefs. But, they also offer less protection against chub rub and chafing.
  • Styles that have longer cuts, like boxers and boxer briefs, tend to work better under business and formal attire, as that was the silhouette they were designed to suit. Alternatively, longer cuts might appeal to you when it comes to sleepwear.
  • Minimal styles like jockstraps are great for high-activity days like gym days, as they keep everything in one place without adding tons of extra fabric that might rub or bunch. And, of course, they’re also sexy pieces that put your assets on display, if you’re into that.

In terms of color, you should always keep basic neutrals on tap: white, neutral (so, your skin tone), black, and gray. Those four can be styled under practically any look. You can also include more dynamic or fun colors and patterns that suit your personal preferences as long as you keep in mind that these may show under thinner or lighter-colored clothing.

Whatever you do, just don’t wear white underwear under white or light clothing. The stark contrast between your skin and the underwear will be more obvious than it would be with a skin tone or gray piece.

Do You Need Undershirts?

Undershirts whether that’s a tank or a tee are designed to sit close to your skin under your shirt. Their basic purpose is to protect your outer layers from the sweat of your skin, all while adding an extra layer of protection from the elements. 

Nowadays, a classic tee worn on its own is an effortless menswear staple, which means it’s worth having a few. It’s always a good idea to keep at least a few neutrally colored undershirts in varying cuts and styles in your wardrobe, especially for wearing under button-downs and flannels. 

If you do plan to wear an undershirt, you’re generally going to want to match it to the tone light, dark, or neutral and sleeve length of your outer shirt rather than trying to match it to your underwear, given that it’s layered under a different piece of clothing. 

Storage and Refreshing Your Wardrobe

To store your undergarment wardrobe, we recommend you sort  into collections based on style, brand, color, occasion, or whatever your biggest considerations are. You may even choose to sub-sort your pieces (aka, go for brand, then style, then color), especially if you have a larger collection. 

From there, you’ll want to fold and store all of the pieces. A Ranger Roll (folding the band of your underwear down, folding the piece into thirds with the waistband at the top, then rolling up to the waistband and tucking the roll into the waistband) is a good option for saving space with larger pieces or longer styles, though a simple square fold or fold in half can work well for higher-cut pieces as well. Once everything is folded, store it in an easy-to-access drawer according to your organization system of choice. 

It’s a good idea to replace worn sets of underwear every six months to a year, so that’s probably also the best time to fully reorganize your collection. During this annual or biannual reorganization, remove everything from its drawer, lay it out, and identify pieces that you’ve either worn through or don’t wear at all. Remove them from your collection, then replace them with pieces that you know you’ll get some good use out of. This is also a good time to try new things that you might not be sure of yet, such as a new cut, color, or material. Let yourself experiment!

Basic Hygiene

When it comes to underwear, there are a couple of rules of basic hygiene that your body (and the people around you) will thank you for following.

  • Change your underwear every day. This is the easiest way to avoid any unwanted smell or bacterial growth.
  • Wash your underwear between every use. Do we really need to say this?
  • Throw out underwear that isn’t holding up. Anything with holes, rips, or excessive stains should go. The same goes for anything that’s losing its shape — no saggy underwear.
  • Avoid excessively tight underwear. This can be both uncomfortable and can cause issues like ingrown hairs and rashes. Know your sizing and size up when you need to.


Whether you’re a novice or a pro, we should all know how to select and maintain the right pieces for us and our daily lifestyles. As long as you’re considering the practical and personal uses of your clothes, building up your underwear basics can be both useful and exhilarating.

Looking to upgrade your wardrobe, but not sure what to try or where to find it? We’ve got you covered. Our subscription service takes the guesswork out of building a functional underwear collection. We’ve got a wide range of popular brands, styles, materials, and colors for you to enjoy, curated to perfection with your preferences in mind. Pick what you want and when you want it, then sit back and enjoy the ride.

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