Free US returns and exchanges Close
Shinesty Image

What Underwear Should I Wear? A Practical Guide To Men’s Underwear

by Nate Charny

Boxers? Briefs? Boxer Briefs? Brief Boxers? When did men’s underwear become so complicated? Back in my day everyone wore either tighty-whities or a swimsuit because all your tighty-whities were in the wash. It’s easy to feel overwhelmed, so let’s break it down to the basics.

Should men wear underwear?

Unless you’re doing a number two or making sweet love (or both #NoJudgment), men should always wear underwear. But men should not wear the SAME underwear year after year. It’s important to get rid of your old underwear before it’s just an elastic waistband with some threads dangling. You need to replace your underwear on a regular basis. I don’t know, let’s say get a new pair once a month. Oh this is a weird coincidence: We offer a convenient monthly underwear subscription you can sign up for right now!

What is the best underwear for men?

No two male bodies are the same. Unless you’re newly born identical twins. But newborns don’t wear underwear. I digress. There are many variables to consider when finding the best fitting pair of underwear for YOUR body. Do you live a sedentary lifestyle? (Like me.) Are you constantly working out? (Like I probably should be.) But there is ONE certainty when it comes to discovering the best underwear for men: The Pouch. Our Ball Hammock® Pouch offers comfortable support for your balls. When your underwear has a pouch, you’ll never sit down and crush your balls ever again. When your underwear has a pouch, your pendulous balls will never swing around and bruise your thighs ever again. When your underwear has a pouch, your life is simply better.

What underwear should I wear?

Choosing the underwear that’s right for you can be intimidating, so let’s take a closer look at the many men's underwear options.

different underwear types


“Going Commando” sounds like you lead a rugged, manly lifestyle. The truth is far less glamorous. The reality is your pants are gonna smell like farts, your “sensitive area” is gonna chafe all day, and there’s a high chance your “sensitive area” gets caught in your zipper and you’ll need to go to the emergency room.


Briefs offer minimal coverage, so if you never skip leg day, this could be the right cut for you. They offer the widest range of unrestricted mobility, which could be perfect if you do an above average number of splits or high kicks throughout the day. Briefs also have that nostalgia factor of those simpler days when you were a little kid and life hadn’t yet beaten you down into the callous cynic you’ve become. If you're not sold on briefs, check out our brief underwear guide.

brief underwear


Trunks are like if your boxer briefs shrank in the wash, but only the legs. A short inseam means your underwear will never hang down below the legs of your cargo shorts. Also, bro, what are you doing wearing cargo shorts?

trunk underwear


No. Just no. Boxers are the least practical underwear option for men, and I’m including jockstraps in that category. Boxers offer no support. Boxers don’t hide your junk from prying eyes when you’re sitting down with shorts on. Boxers cause your “sensitive area” to chafe against their rough fabric. Boxers bunch up under your pants and need to be constantly adjusted. The only thing boxers do is add a layer of fabric between your butt and your pants. And if that’s all you’re looking for in a pair of underwear, just slap a square of toilet paper over your butt and call it a day.



A slightly better choice than boxers. You get ball support at least, which is something. Of course, it comes at the cost of any butt coverage, so you’re gonna run into the same odor related issues as going commando. Leave jockstraps to the pros.


Boxer Briefs

Quite possibly the perfect men’s underwear ever invented. Boxer briefs offer good coverage, plenty of support, and are flattering to your figure. Boxer briefs are the vanilla ice cream of undergarments. It’s the most popular flavor in the world for a reason. And while vanilla may not be exciting, it gets the job done, damnit. All our underwear cuts are variations on boxer briefs. Some may have long legs or a fly, but they all have the sturdy, reliable base of boxer briefs. To put it simply, start your underwear journey with boxer briefs and then see where the adventure takes you. If you don't feel like you know enough about boxer briefs yet, check out our blog post on why boxer briefs are the best.

boxer briefs

Boxer Briefs with Fly

Re-read the paragraph above and then add ANOTHER great feature. Boxer Briefs with the fly give you easy access to your business when it’s time to use the bathroom. NOTE: This only applies to number ones. Please don’t try to poop through the underwear fly. If you need more info on what the hole in underwear is for, we've got you. But what the fly is really all about is having options. You can still flop over the waistband if you want, but now at least you have a choice.

boxer brief with fly

Long Leg Boxer Briefs

I hate to keep saying this, but re-read the last TWO paragraphs and then add ANOTHER great feature. This cut of underwear has – wait for it – longer legs than standard boxer briefs. This gives you maximum coverage for crisp October mornings. Or if you live in the Southern Hemisphere, I think crispy July mornings maybe? But if you’re nervous about the legs of your underwear riding up when you stand up and sit down, long leg boxer briefs are the cut for you. A great option if you want to be a tease and let a little underwear peek out from the legs of your cargo shorts. By the way, nice cargo pants, bro!

long boxer briefs

Cooling Boxer Briefs

This is the perfect style if you want to be on the cutting edge of underwear technology. The future is here today, people! Our cooling boxer briefs are made of a patented fabric infused with natural cooling minerals that’s been scientifically proven to keep you up to 3 degrees cooler. They’ve also got strategically placed mesh panels to increase airflow and stop sweat before it starts. They’re quick drying, hyper wicking, and basically are the most luxurious underwear money can buy right now. Plus, we came up with the name paradICE™ which is pretty cool.

cooling boxer briefs

Of course, you don’t have to limit yourself to just one style of underwear. Try a bunch! Maybe on Mondays you’re a briefs guy but by the time Friday rolls around you’re all about those long legs. A well-stocked underwear drawer is full of different cuts.

Shinesty Image

Stay Weird & Never Back Down