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Home / Blog / Clothing and Style

6 Types of Men’s Underwear: Choose Wisely!

Published on April 18, 2022 by TMM Staff · Clothing and Style May contain affiliate links (what's this?)

Want to learn about underwear styles other than just regular boxers or briefs? We’ve created an in-depth guide to help you choose the perfect pair of underwear for you.

Table of Contents

  • Boxers
  • Briefs
  • Boxer Briefs
  • Trunks
  • Pouch Underwear
  • Long Underwear
  • Questions About Men’s Underwear
    • Which Type of Underwear Is Best for Males?
    • What Is the Hole Is Men’s Underwear For?
    • How Many Pairs of Underwear Should a Man Own?
  • Which Type of Underwear Will You Wear?
Tommy John underwear review

Underwear is the unsung hero of any man’s wardrobe. Even though your underwear isn’t visible (well, ideally), it’s still an important piece of clothing. A poorly chosen pair of drawers can become uncomfortable throughout the day.

Whether you’re working out, finally getting to the next step with that special someone, or just needing a reliable and comfy pair of underwear, we’ve got you covered. 

Boxers

If you’re looking for a roomy fit, boxers are probably up your alley. 

The reason they’re called boxers is that they were literally invented for boxers. In 1925, Everlast’s Jacob Golomb came up with a brilliant idea in creating a trunk that had an elastic waistband and provided freedom for boxers to move around the ring. 

Tommy John Second Skin Boxer
Tommy John Second Skin Boxer

The boxer short was seen as a masculine style that men favored and because of this, boxer shorts were soldiers’ first choice of underwear at the time. The popularity of the style soon soared. 

Fast forward to now, and boxers have evolved quite a bit. They can now be found in the form of a trunk, boxer brief, and midway boxer brief.

Briefs

You probably wore good old tighty whities growing up. While these are often overlooked by men once they reach adulthood, there are actually some good reasons to go back to briefs. If you’re looking for more coverage and want everything to stay in place throughout the day, the brief is your best bet.

Tommy John Cool Cotton Brief 2.0
Tommy John Cool Cotton Brief 2.0

This popular garment was first created and sold in 1935 by Coopers Inc. The Wisconsin brand called them “jockeys” because of the underwear’s similar design to jockstraps. 

Since then, the brief has evolved and can now be found in several iterations like the trunk and boxer brief.

Boxer Briefs

Last but not least, we have boxer briefs. Marrying both the boxer and brief, this cut of underwear takes the best of both worlds and combines them.

Tani Mesh Boxer Brief
Tani Mesh Boxer Brief

This style provides form-fitting coverage and gives you a bit more length than trunks. If you’re still on the fence between the brief and boxer, the boxer brief could meet your needs.

Trunks

Not to be confused with the boxer brief, the trunk is a separate cut of underwear that is another great option. 

Vilebrequin Flat Belt Swim Trunks front
Vilebrequin Flat Belt Swim Trunks

What makes these different is the length of the inseam. Trunks are usually shorter, so they’re great for both practical and romantic reasons. So if you’re looking for something in between the brief and the boxer brief, or if you want to impress that special date, trunks might be for you.

Pouch Underwear

Pouch underwear takes boxer briefs to a new level. This specialty undergarment was invented to prevent chafing from occurring. 

Tani pouch underwear
Tani Pouch Underwear

Befitting its name, pouch underwear separates your privates, preventing them from continuously rubbing on your leg throughout the day.

Long Underwear

Also known as “long johns”, this form of underwear was created for men in colder climates. Fittingly, long underwear features a much longer leg, which provides warmth and comfort during the colder months. 

Tommy John SleekHeat long john
Tommy John SleekHeat Long John Bottom

Nowadays, long johns can be found with technology-packed fabrics that allow for maximum breathability while still retaining heat.

Questions About Men’s Underwear

Here are the answers to some common questions about men’s underwear.

Which Type of Underwear Is Best for Males?

A lot of men prefer boxers or boxer briefs, but the best type of underwear is subjective. Whichever style makes you feel comfortable and confident is the best style!

What Is the Hole Is Men’s Underwear For?

The hole in men’s underwear is to make it easier for men to pee without removing their underwear.

How Many Pairs of Underwear Should a Man Own?

Different guys have different needs, but as a general rule of thumb, it’s good to have at least two weeks worth of underwear.

Which Type of Underwear Will You Wear?

Underwear can be difficult but sticking to the essential cuts above will keep you head-ache-free on your next shopping trip. We hope this guide on underwear styles has been helpful. Now you’ll know exactly what styles are best for your body. 

Questions? Comments? Leave them below!

Clothing and Style boxer briefs, briefs, underwear

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About TMM Staff

The Modest Man staff writers are experts in men's lifestyle who love teaching guys how to live their best lives.

If an article is published under TMM Staff, that means multiple writers worked on it. For example, sometimes several of us have experience with a certain brand, so we collaborate to publish a more thorough review.

Or, if an article was originally written by one person, but then it was updated by someone else, we'll re-publish it under TMM Staff.

Remember: all of our articles (including those below) are written by real people with decades of combined experience in men's fashion and lifestyle topics.

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    Got questions? Want to share your opinion? Comment below!

  1. Style Wallah says

    April 21, 2022 at 6:25 pm

    “The hole in men’s underwear is to make it easier for men to pee without removing their underwear.”

    What’s the expectation here, that we weave our junk through the hole to go pee? Without pulling our underwear down? Does anyone actually do this????

    Reply

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