The Best Boxer Briefs And Trunks In 2021

In an age where budgie smugglers and long johns are about as rare as top hats and tails, one underwear style reigns supreme – the boxer brief. Those beady-eyed Poirots out there will have noticed that the name is a hybrid of ‘boxer’ and ‘brief’, which is precisely what they are: a garment with the length of a boxer but with the tighter fit of a brief (those cut a little higher are often called trunks). The snug fabric makes them easier to slot under trousers than the billowing boxers, which have the tendency to bunch in unpleasant places. Often attributed to designer John Varvatos, who was head of menswear design at Calvin Klein in the early nineties, the style actually goes at least 10 years further back. Boxer briefs tend to sit around the middle of the thigh, which means they cover a lot more ground – especially around the back, without going all puritan. With that covered, here’s what else you need to know:

Buying Considerations


For the most part, boxer briefs and trunks will be made out of cotton, which has the luxury of being naturally breathable, soft and hypoallergenic. Not all types of cotton are created equal, mind. Pima cotton is the stuff for A1 levels of luxury and comfort. Most boxers will be made out of a cotton-elastane blend to give them the elasticity needed to adhere to your curves. The higher the elastane percentage, the closer the underwear will cling to your body. Other fabrics out there include modal, a type of semi-synthetic which mimics the softness of cotton but with increased sturdiness (which will help them last longer), linen which has low heat conductivity making that whole area a cooler place and silk, which has a soft and luxurious feel but also carves you out as some latin lover with a penchant for red velvet robes and not getting up till midday. Actually, that doesn’t sound too shabby.


Black is best when picking the colour of your boxer. Dare we say it but the darker shade will be more, er, forgiving and also tends to look smarter should any fabric peek out over the top of your dark coloured trousers. White and lighter shades of boxer work alongside indigo denim jeans and beige chinos.


Finally, don’t go waiting till Christmas to replenish the stocks. If you’re on a seven-pant rotation, think about swapping out twice a year. How do you know your knicks are knackered? Look for fading, loss of elasticity around the leg and, ahem, discolouration, should be all the proof you need.

The Best Brands For Boxer Briefs

Calvin Klein

From references in Back To The Future to making a star out of Mark Wahlberg, Calvin Klein is arguably the most recognisable name to pop its head above the top of your jeans. Its iconic logo waistband never fails to make a statement, but it’s best known for the second-to-none support of its boxer briefs, with just the right amount of elastane in the cotton blend to hug the hips. Just don’t expect to look as good in them as Marky Mark. Buy Now: £38.00

CALVIN KLEIN UNDERWEAR Three-Pack Low-Rise Stretch-Cotton Boxer Briefs


Superior materials at inferior prices have made Uniqlo a high street go-to ever since the Japanese retailer expanded overseas at the beginning of the millennium. Expect the same quality in its boxer briefs, spun from first-rate, super soft Supima cotton that will cushion you, and your bank balance. Buy Now: £5.90



Heritage underwear brand Jockey has had a US bestseller since 1935 with its briefs – all but wiping out the long john in the process. The shape and fabric are old-school, with a little more length in the leg than others, and a 100 per cent cotton construction without the modern day stretchiness. Buy Now: £13.00

Jockey Classic Cotton Rib Midway Brief Underwear with Y-Front Fly

Ralph Lauren

If you’re going for brand recognition with your boxer briefs, Ralph is your boy (although we’d advise against flashing your waistband outside the comfort of your own bedroom). The iconic polo player motif frequently features in the range, which goes for a slightly shorter length and a tighter fit than others. Buy Now: £25.00

POLO RALPH LAUREN Cotton Boxer Brief

Hamilton And Hare

Hamilton and Hare excels at considered loungewear and underwear for the discerning, oh-so-classy bloke. The boxer brief is one of the original styles from its beginnings in 2012, coming in a plush jersey fabric and featuring a covered waistband to protect your navel from any bothersome elastic rubbing. Buy Now: £35.00


Björn Borg

As imperious in the underwear world as its namesake founder was on Wimbledon’s centre court, Björn Borg focuses on well-fitted underwear, wild patterns and high-performance materials. The fit tends to be a little longer with a mid-rise that sits above the hip, all of which adds up to a boxer brief that is perfect for athletes and gym goers. Buy Now: £25.00



Next-level basics have been the bread and butter of British heritage brand Sunspel since 1860. Having pioneered the development of most luxury undergarments as we know them today, it’s little wonder that it counts James Bond among its famous wearers. The cotton used for its boxer briefs is impeccably soft with a sleek and simple finish that purrs elegance like a shaken martini. Buy Now: £35.00


Emporio Armani

Calvin Klein might have had Marky Mark, but Armani had David Beckham. Celebrity endorsements aside, boxer briefs by the Italian luxury fashion house follow a similar blueprint with the masquerading logo waistband, a tight fit, and at just a fraction of the cost of an impeccably tailored suit. Buy Now: £36.00

Emporio Armani - 3 pack assorted trunks

Derek Rose

Derek Rose sits atop London’s pyjama set, but the Marylebone-based label also knows how to make a mean pair of boxer briefs. The Japanese Pima cotton used is noteworthy, but what truly sets it above the rest is the intricate patterns, from pale blue pagodas to elephant taxis. Buy Now: £40.00

Men's Hipster

Marks & Spencer

A British institution and bastion of the high street, Marks & Spencer maintains its popularity by turning out quality garments with a considered cut and expert attention to detail. Its boxer briefs are made out of a comfortable jersey and often come in multi-packs, which make them some of the best value for money buys anywhere. Buy Now: £18.00

M&S COLLECTION 3 Pack Cool & Fresh Pure Cotton Boxers

Paul Smith

He’s one of the most respected names in fashion, but Paul Smith simply won’t rest until he’s decked out every single garment clothing your body, and that includes boxer briefs. His signature on the waistband will show off your fashion chops, while the range comes in safe monochrome shades alongside some decidedly zany patterns, as is Sir Paul’s way. Buy Now: £36.00

Men's Classic Boxer Briefs Three Pack


Bringing that world-famous German engineering into smalls may seem a tad excessive, but underwear brand Schiesser is really at the top of the game when it comes to this stuff. The elasticated waistband is designed not to constantly pinch like it’s the last day before payday while little luxury touches like mother-of-pearl buttons and a swish cotton jersey make all the difference. Buy Now: £95.00

Schiesser three pack boxer briefs

Similar Articles