Mens Underwear Styles: Choosing the Right Fit for You

The world of mens underwear is vast and varied, offering not just comfort but also style and support where it matters most. Yet most men have a favourite type they prefer.

There is a vast difference between female and male intimate apparel, with body type not impacting choice of style, and VPL’s not even a consideration. For men, it’s nearly always a case of comfort levels and support for the genitals. That and habit; where it’s likely they have been wearing the same type since young adulthood.

briefs vs boxers jpg
Briefs vs boxers (trunks style)

What is the difference between briefs and boxers?

The difference between briefs and boxers is in their design, length and fit. Briefs are snug and offer more support, while boxers were loose-fitting and provided more freedom of movement. However modern tighter fitting boxer briefs or trunks (pictured) have replaced traditional boxer shorts.

For me personally, when I was a young boy, my mum used to buy me Y-fronts briefs (it was the 80’s), and in my teenage years I moved on to designer boxer shorts. And then at some point I moved to trunks, which for me is the ultimate in men’s underwear styles.

My swimwear choice was a similar trajectory, with childhood speedo’s progressing to long board shorts, to mid-length designer brands. Both paths are highly likely to correlate with consciously loathing my skinny legs.

And legs actually are the main reason you’d even worry about the right fit and it’s the same principle as your swimwear. If you have long legs skinny like me, then longer boxers look best. If you have short muscular legs, briefs or trunks for the win. But ultimately it’s comfort than breeds confidence.

chiselled man in trunk briefs jpg
What sort of grundies man are you? Boxers or briefs?

Understanding the Types of Underwear for Men available

When you’re buying mens underwear, it’s often comfort and functionality vs fashion. Luckily, us men are rarely seen undressed, and pay little attention to others in the gym changing room. I literally have no idea what any of my close friends wear, although I could make a very educated guess by their choice of swimwear.

While women will be worried about coverage, see through material, matching, visible panty lines AND body shape, we get to wear our big kid pants without a care in the world. No flossing thongs, camel toes or wedgies from panties for us to worry about.

The only fashion faux-pas I’ve ever made in my many decades on this planet was to buy some silk boxers. And that taught me that material matters and was never repeated. So fabric is important, and stretch cotton is a classic choice for a reasons, offering breathability and comfort for everyday wear. Plus absorbent for any errant dribbles. My other sage advice is I always avoid the tighty whities in favour of black, I skid you not.

For those leading an active lifestyle, moisture-wicking fabrics like microfibre and modal keep you dry and comfortable during intense activities like running and sports. Don’t overlook bamboo fabric; it’s eco-friendly, hypoallergenic, and provides excellent moisture absorption.

In market share today, popularity order is boxer brief, briefs, trunks and boxer (which peaked in fad popularity in the 1990’s and early 2000s).

Men really come into two camps, briefs or boxers (and it’s more popular tighter fitting variants now to suit any activity). And the difference is really how much material extends down the thighs. So for consistency, lets compare these with the brand that redefined underwear in Calvin Klein. No Y Front underpants here, but they are a style of brief if you need that clarity. Onto the mens underwear style guide.

Calvin Klein mens underwear styles and types
Top row (L-R) Boxer, Boxer Brief, Trunks, (Bottom Row L-R) Low rise Trunks, Jock Strap, Briefs

The Classic Briefs

Lets start with the classic briefs, aka the jockeys. First sold in 1935 as the Jockey Y Front due to similar support as a jockstrap used playing sport. It’s defined as short, form-fitting underwear and swimwear, with a secure waistband that sits comfortably around your hips, attached to fabric that runs along the pelvis to the crotch and buttocks.

For men like me, I simply envision the late, great, Rik Mayall in Bottom wearing big white Y-Front underpants. That look will put me off for life. Although of course you mostly see flyless varieties on sale, which is the second most popular style of underwear.

Swing low with Boxers

While classic briefs offer snug support, boxers elevate comfort with their loose fit and breathable design and full coverage, making them a go-to for those valuing freedom and ease throughout their day. If you want loose-fitting underwear, then a pair of boxer shorts is for you.

They are baggy because they were launched in 1925 by the brand Everlast, who continue to make clothing designed for boxing to this day. Yep, they are literally boxing shorts, invented for men to box in. The revolutionary elastic band wore more comfortable than the leathered belt version in use at time, and this inspired a move from outerwear to underwear.

Now, boxers are the least popular of the standard underwear types, ignoring things like the bikini obviously.

levi ad laundrette 1985 jpg
Ads were making mens underwear sexy

They became a US army staple much like the t-shirt, and in 1947 John Hill of Sunspel (that’s the brand with the James Bond Casino Royale Polo) brought it to the UK. Where it eventually took off in that 1985 Levi’s commercial in the laundrette.

The rest came with the Calvin Klein underwear branding, 1992’s Marky Mark ad campaign (which was more the boxer brief style in fairness and basically a cut off pair of long johns), and the low-slung baggy jeans of hip hop style to show off the branded waistband as a status symbol.

Why we chose to wear the baggier boxer shorts with open gap for a fly in the 90’s is a bit of a mystery to me in all honesty, although there were wild rumours it was better for future fertility. There was no support and accidental falling out was common, but everything was worn baggy then so guess it was that. But at least we could use the phrase “how’s it hanging”, even if it did feel like we were free-balling.

man in white boxers jpg
Men’s boxer shorts combine style and comfort and can be plain or colourful

Boxer Briefs

Bridging the gap between comfort and support between the two, boxer briefs offered the best of both worlds with their snug fit and breathable fabric. They were similar to boxer shorts in length, but tight-fitting like briefs.

Usually made of a combination of cotton and spandex, polyester, they can have a keyhole fly, button front, pouch, or no fly at all. The waistband is usually a separate band of elastic material with the manufacturer printed on it, often in a contrasting colour to the main material.

Trunk Briefs

Are they shorter boxers or longer briefs with leg sections? Either way, trunks are a great middle ground and work best for coverage and support. A supportive snug fit around the derrière, with a blend of comfort for the crown jewels, the perfect harmony for the modern man’s needs.

There is also a low-rise version, which is designed to be lower waisted. And high-rise which is higher than the hip bones.

All of the designer brands like Hugo Boss, Tommy Hilfiger, Armani, Ralph Lauren. and Paul Smith, all have a huge range of men’s underwear offers available in a variety of modern styles.


I have to cover jockstraps, firstly as I put an image of them up and they are making a comeback of sorts, and secondly because the name spawned a whole subculture of American athletic types who wore the protective undergarments so deserve a mention.

A jockstrap is an elastic waist band with a support pouch that can take a box, and some side straps. It sort of looks like someone cut the rear end off so briefs, but actually was invented many years earlier for bicycle couriers, which on cobbled stones I get.

But I don’t understand why they are not a relic of the locker room, unless you are using them for protection for your package when playing sports. As a fashion item, they should be confined to the sealed laundry basket, along with the man thong and mankini, never allowed to see the light of day again.

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Soft cotton briefs can be sexy, having a muscular body and sock stuffing may help

Sexy Mens Underwear

While ladies have a far better range of intimate lingerie and raunchy underwear, there is a whole range of men’s sexy wear too. You’ll discover designs that not only enhance comfort but also elevate your style with daring cuts and luxurious materials. From sleek, form-fitting briefs that accentuate your physique to bold, lace, mesh, and cut-out details for a playful yet sophisticated edge.

You’ll find that these pieces are designed to make you feel as good as you look, prioritizing both aesthetics and comfort. Whether it’s for a special occasion or just to add a spark to your everyday wardrobe, embracing this trend can transform the way you see mens underwear.

Step into something that makes you feel daring and desirable. And remember, the best fit isn’t just about what’s in vogue; it’s about what feels great and boosts your confidence.

roman gladiator in the arena jpg
We who are about to buy, salute you (in thanks for this underwear guide)

A Brief History of Men’s Underwear

We’ve covered different types of underwear, but no doubt you are full of questions. Like why is it a pair of underwear when it’s just one? And why do American’s call trousers pants?

Well lets start at the beginning, which was likely when Ug the caveman didn’t like the chilly ice age wind on his plums and the shrivel of his appendage, and decided to use a loin cloth to cover up.

We know in ancient civilizations such as Egypt, Greece, and Rome, men wore simple cloth garments, wrapped around the waist and between the legs for modesty and protection. Ancient Romans wore a subligaculum in the form of a pair of shorts or simple loincloth wrapped around the lower body. In particular, it was part of the dress of gladiators, athletes, and actors on the stage.

During the Middle Ages, men’s undergarments consisted of braies, a type of trouser worn by Celtic and Germanic tribes. This loose-fitting linen or woollen shorts were tied at the waist. These typically extended to the knee or mid-calf.

Pantalone were a traditional type of trousers (but more like leggings) in 16th-century Italy which gained in international popularity, although there is also a character of the same name often referred to as the source. Either way, it was anglicised as pantaloon, and then much later shortened to pants.

As the new world was gaining it’s own personality and dialect, us brits changed it to trousers, while our American cousins kept the pants. And then rightly started calling underwear underpants to go underneath your pants. In the Northwest of England, some people also use the American version.

To confuse matters, you also have breeches (britches) which are also tight fitting knee length shorts that started life as underwear, with breeks used in Scotland.

In the 1600s we have to reference the trousers Dutch settlers wore when they arrived in New York. These pants that rolled up just below the knee became known as Knickerbockers, which didn’t just give their name to the New Year Knicks, but also knickers.

Moving on to the 19th century, firstly the sewing machine was invented in 1830, but this wasn’t for the average peasant. It’s assumed that undergarments were two separate legs that were drawn up and tied in place. Hence the name pair of drawers (and not related to the underwear drawer).

There is also plenty of UK based slang terms for undies, including kecks and bills (Liverpool), chuddies (British Asians) and skids in Scotland (although of course a true Scot would wear nothing underneath the kilt.