Most Comfortable Men’s Underwear in 2024

Surely, the most important aspect of any underwear must be its level of comfort. You don’t want discomfort in your life. None of us do! Discomfort is stressful. It  antagonises your very existence. 

Comfort makes everything easy breezy and that much more pleasurable. And you will certainly enjoy life that much more if you’re wrapped up in a lovely, comfortable pair of undies. 

Of course, no underwear is engineered to be uncomfortable on purpose. What on Earth would be the point of that? Of course, you have your Calvin Klein and your BOSS - giants of underwear, well-known for the comfort and wearability of their underwear (as well as the kudos for fashion icon status). But what about some lesser-known picks?

Comfort is, after all, a subjective business. What one man finds irresistibly comfortable and luxurious may utterly turn off another - it’s all down to personal choice. 

When we asked the Pantsman what we should focus on when looking for the most comfortable underwear, he was suitably succinct: fabric, pouch, backside, thigh and waistband.

And we can see what he means… find a pair of pants that fit you properly at all five points and you will be wearing a supremely comfortable pair of pants ...

But, we asked, can’t you provide just a bit of guidance? We, and our customers, cannot try on every pair of pants. And trial and error can be an expensive business.

So with a wry smile the Pantsman pulled from his pocket, his list of the most comfortable men’s underwear. And we can share it with you now. We are here to guide you towards comfort and happiness. 

7 most comfortable pairs of men’s underwear

Calvin Klein Trunks

Best for everyday comfort (tied)

Calvin Klein 3 Pack Trunks for men 2021

Calvin Klein is quite possibly the most well-known underwear brand in the world. Its fame reaches to the stars and back - for good reason. Calvin Klein consistently produces some of the most comfortable and wearable pants on the market.

These trunks are no exception. Coming in a range of understated colours, they represent the very best of everyday comfort in men's underwear. The branding is emblazoned clearly across the thick, elastic waistband for added flair, which sits just below the hips; the cotton/elastane material is soft to the touch and stretchy in all the right places; and the cut is flattering to the figure and guaranteed to make you look like a sexy beast. 

There is only one other brand who can compete with CK for everyday comfort...

BOSS Trunks

Best for everyday comfort (tied)

BOSS 3 Pack Trunks for men 2021

…and that brand is, of course, BOSS. Just as famous for all the right reasons, BOSS doesn’t cut corners with its signature underwear either. 

Made from stretch cotton for a flexible and breathable feel, these trunks  are engineered with everyday wear in mind. Again the waistband is not too high and the leg sits comfortably at the top of the thigh and the coverage at the rear is supportive and provides definition. Of course, the material plays an important role in this - it is soft to the touch and with enough stretch to maximise the comfort. They are the best all-purpose you will find, whether you’re in the office, on the road, chilling with friends or anything in between. 

BOSS and CK have the everyday comfort market nailed and we can’t recommend either of them highly enough. 

Derek Rose Amalfi/Gingham/James/Savoy

Most comfortable boxer shorts

Derek Rose James Boxer Short for men 2021

Derek Rose is a slightly lesser known British brand… but man, it should be on your radar. It produces the most luxurious and comfortable boxer shorts known to man or beast.

Every pair of boxer shorts by Derek Rose is crafted with luxury and comfort in mind. The pure cotton batiste fabric is extremely soft to the touch. The loose fit is perfect for those of you who want freedom of movement and don’t want to be constricted by an elastic pouch.  And, to improve your comfort further, the gentle elastic waistband is adjustable. 

They’re perfect for lounging. Perfect for wear under loose clothing. Perfect for sleeping. Lightweight. Soft touch. These boxer shorts are the final word in comfort. Sure, they have a premium price point… but can you really put a price on luxury? 

HOM HO1 Mini Briefs

Most comfortable lightweight underwear

HOM HO1 Mini Brief for men 2021

If your primary concern when looking for a comfortable pair of pants is lighter weight, then you’re in the right place with HOM. These HO1 Mini Briefs are as light as they come. In fact, they are so light, you’ll barely even know they’re there…

Not only are these briefs engineered and designed with inclusivity in mind - the horizontal opening is suitable for right or left handed individuals - the fabric is so soft and light, it almost acts like a second skin. This is down to the modal cotton used. It’s one of the softest, most breathable, and highest quality materials available for pants production. It is also great for gents who tend to overheat.

Couple this with the fit and you’re on to a winner with these lightweight pants. The high cut means your legs will experience total freedom, whilst your package will be gently supported thanks to the modal cotton’s soft elastic properties. The waistband sits below the hips and is very unobtrusive.

These are some truly comfortable briefs and aren’t to be missed if you’re looking for lightweight pants.

SAXX Vibe Boxer Briefs

Most comfortable slim-fit underwear

SAXX Men's Vibe Soft Boxer Brief

If you’re tired of your boxers or boxer briefs rucking up under your clothes and causing a nuisance, then SAXX has you covered with its Vibe boxer briefs. 

The slimmer fit of these pants ensures that there’s less fabric to fold and bunch up around your legs, leading to a closer and more comfortable fit to combat chafing before it rears its ugly head. 

Couple this crafty slimmer fit with SAXX’s breathable and moisture-wicking fabric, and you’ll stay fresh and chafe-free all day long. Moreover, SAXX is a great choice for those who love to make a statement with their underwear. The Vibe style is available in a huge variety of prints and makes for a striking, yet comfortable pair of pants that you’ll be proud of. 

CR7 Cotton Trunks

Most comfortable underwear for men on a budget

CR7 3 Pack Cotton Trunk for men 2021

If you’re on a bit of a tighter budget then this 3 pack of trunks from CR7 cannot be beaten for their comfort.

Part of the range concepted by the one and only Christiano Ronaldo, these pants were engineered for comfort, quality, and high performance. His mantra is that no man should be without some quality pants in his drawer - and we certainly agree with him. 

Fortunately, he also believes that you shouldn’t have to break the bank to get some quality pants. These trunks are a cotton/elastane blend, designed for comfort, stretch, superior fit, and endurance. They’re built to last and are more than capable of accompanying you on almost any activity you can think of, all while keeping you supported and wrapped in soft comfort. 

Some real winners here if money is on your mind. 

So what men’s underwear is the most comfortable?

If you’re looking for some pants to simply lounge about in, take a lazy day, sleep or generally relax in, then Derek Rose is the final word in luxury and comfort. 

If, however, you want pants that offer a bit more in the way of support, for wearing out and about, then SAXX Vibes and CR7 cotton trunks will keep you comfortable till the cows come home. They offer great support and superior comfort. 

After something a bit smaller? Go for the HOM Mini Briefs. They basically feel like a second skin and are extremely lightweight. Another great choice, especially if you’re conscious of the planet, are the boxers from Panos Emporio. The bamboo/cotton construction of these is effortlessly comfortable and great for Mother Nature to boot. 

And finally, the kings of everyday underwear are BOSS and Calvin. These should be your go-to brands if you’re looking for everyday comfort and that all-important dash of style in your underwear drawer. 

At the end of the day, what you find the most comfortable is entirely up to you - we won’t tell you what you should and shouldn’t find the most comfortable. That is not our job. We are merely the guiding hand. 

If you feel ready to take the reins and grab your next pair of pants, feel free to shop our full men's underwear range right now. Do also keep in mind that finding the right fit is crucial in getting the most comfort out of your underwear, so make sure to read our handy underwear size guide now if you don’t know your underwear size. 

If you want more info on other pants and sock-related topics, keep up to date with our Below the Belt Blog. Otherwise, happy hunting. Get out there and find your next luxurious and comfortable pair of pants!