The History of Underwear: A Brief Flash

5 min read

Table of Contents

  1. Loincloth
  2. Braies
  3. Codpiece
  4. Long Johns
  5. Boxers
  6. Briefs
  7. Boxer Briefs

Ask about the greatest invention of humanity and you’ll get all sorts of answers. Things like the wheel, philosophy, penicillin and even the internet will come up. Some might even throw sliced bread into the bunch. But one thing you won’t hear about is underwear.

We're here to change that.

Can you imagine going for a run with your nuts dangling around and hitting each other like two cherries on a swing ? Or worse, feeling the prickly harsh wool from your slacks inside your butt crack in the middle of the summer.

All of a sudden, modern underwear like micro modal underwear doesn’t seem like an insignificant invention anymore, does it?

Well, that’s because it isn’t. And it’s about time we stopped shortchanging the worth of our shorts.

Let’s get to the bottom of the history of men’s underwear. And don’t worry, we promise to keep it brief!

Loincloths, Breaches, and Brazen Codpieces

March some 7,000 years in the past and you’ll get the perfect lesson on why we needed underwear in the first place.

When the prehistoric man went out on a hunt, he needed to be swift, agile, and always alert. Staying sharp in tense situations took a ton of effort and discipline.

But no amount of willpower can keep you from losing focus when your twig and berries are scratching against, well, literal twigs and berries around you. And that’s how we got the first underwear in the history of mankind: the loincloth.


Made of a single piece of cloth and wrapped around the groin and hips, the loincloth did a fine job of keeping everything tucked in place and safe from the commotion of daily life.

From the Ancient Egyptians and Chinese to Romans and Greeks, everyone had their own variation of this type of underwear. The Pharaohs in particular were fond of their loincloths as they took extra supplies to the tomb with them, sometimes up to 145 spares

Things remained unchanged for thousands of years. But then came the Middle Ages, which brought a new style of loose-fitting trousers called "Braies" into fashion.


These knee-length laced-up breeches were worn under long tunics to keep the outer clothes clean. But when the time came for answering nature’s call, all the lacing and cinching sure didn’t help. Luckily, the Medieval man finally got a solution in the form of the infamous codpiece.


Having a pouch next to your crotch that you could unbutton at a moment’s notice was a huge relief. But then came King Henry VIII, who started padding his codpiece to show how big his, uh, crown jewels were.

The English court soon followed suit, and the whole thing turned into a royal dick-measuring contest. Nothing more manly than a big ol' bulge in the crotch to assert dominance and charm the ladies. Ain’t that right, fellas?

Luckily, the codpiece was short-lived as it ran out of fashion by the turn of the 16th century.

The Battle of Boxers and Briefs

It took many centuries before underwear looked anything like the pairs we’ve come to cherish today. There were tighter breeches, single-piece union suits, and lots of other variations along the way. But all that changed when we had an epiphany: underwear can be more than just a piece of cloth to cover up our jewels.

All of a sudden, everybody wanted to wear something that made them look like a man’s man!

Long Johns

Take the long johns as an example. You know where the inspiration came from? John L. Sullivan. A bare-knuckle boxer of the 19th century who wore long underwear to the ring. Hence the name long johns.

In case you haven’t figured out where we’re headed with this, it didn’t take long for someone to think, “Hey, what if we made those shorter and put some elastic in it?” And Everlast was the company that cracked this nut and came out with the first mainstream pair of boxers.


The great thing about boxers is they give our balls some room to breathe. But where they kind of suck is how they leave everything dangling. Just like dangling modifiers piss off grammarians around the world, dangling balls left many men hanging.


Enter briefs. Inspired by the jockstraps worn by cyclists, the Chicago-based company Coopers came up with a revolutionary design that mixed support and sexy into one package.

And to say that it was an instant hit would be, well, nothing but the truth.

Imagine this scenario. January 19, 1935. A Marshall Field’s State Street store in downtown Chicago makes the brilliant decision of putting up the first pair of briefs on a mannequin near its windows—get this—in the middle of a blizzard!

The first thing you’d expect out of that scenario is for the brilliant decision-maker to get fired. But that didn’t happen. That brief exposure is all it took for these snug cousins of the classic boxers to cause a stir in the city. So much so that the company Cooper changed its name to Jockeys. And that was probably a smart move considering their product ended up selling 30,000 units within a few months of the lousy launch.

And that’s how the world got both boxers and briefs.

Fun fact: This is the same time period when beaches in the US started allowing men to go topless. Bet you didn’t know that was a thing!

The Rise of the Boxer Briefs

Picking between boxers and briefs is nothing short of a conundrum. One lets your balls breathe but leaves them hanging. The other keeps them tucked and all, but like a clingy Tinder match, leaves you wishing for more space.

Something had to change. And change it did!

Boxer Briefs

In comes Mark Wahlberg with the iconic 90s ad for Calvin Klein, sporting the nation’s first mainstream pair of bright white boxer briefs—ball-cupping, snug-fitting, close but far from clingy—a complete game-changer in the world of men’s underwear.

These hybrid pairs of underwear combined the best of boxers and briefs into what today is the most popular style of men's underwear, the boxer brief.

The rest is history as we all know it.

Marky Mark found his way into the hearts of millions, and our beloved boxer briefs made their way into the drawers of millions more.

Now, don’t get us wrong. Boxer briefs were a fantastic step forward, but they weren’t perfect. We’d know ‘cause we just spent a good part of the last decade ironing out the kinks in their design, and trust us, not the fun kind of kinks.

Ball pinching. Swamp Crotch. Creasing Waistbands. Underwear that rides up. You know the drill.

But beyond comfort, most boxer briefs are just plain boring.

Sure, they’re a step up from the tighty whities adored by grandpas and prepubescent boys around the world. But that’s like a bottom comparison, both figuratively and literally!

Now, if you're looking for buttery soft boxer briefs that are more eye-catching than Marky Mark’s washboard abs, you've come to the right place.

Check out our collection of softer than soft boxer briefs to ever lay claim to your crown jewels.