5 Best Boxer Short Brands for Men, From Calvin Klein to Hugo Boss

Boxer shorts are the ultimate wardrobe staple. As the first thing you put on and the last thing you take off each day – and the layer that sits closest to your skin – they really are the foundation of every outfit. Kit out your bottom drawer with the very best men’s boxers and you’ll have the basics you need to build a sartorially sound look from the inside out.

What constitutes the ‘right’ style – be it boxer shorts, trunks or even briefs – is a matter of personal preference, and also depends largely on what you’re using them for. Playing sports? You’ll need the strong support offered by trunks. Prefer to feel the wind beneath your wings? Keep your crown jewels comfortable by investing in soft, loose fitting boxers.

What shouldn’t be a matter of preference, though, is the condition they’re in. Anything less than a fresh, clean pair each day is not only gross, but unhygienic – so make sure you’re washing them between wears. And if your pants are looking moth-eaten, it’s time to replace them. Trust us: if you don’t take an interest in your boxers, no one else will either. As a rule of thumb, you should aim to inject new life into your undies drawer every couple of months.

When you’re shopping the best men’s boxers, there are plenty of quality brands worth splashing your hard-earned cash on, from Calvin Klein and Hugo Boss to Armani. But before you whip out your credit card, not all styles are created equal. When it comes to what you wear underneath your outfit, there are a few key factors that you need to take into consideration. Read on to get the right pair in your armoury.

The Fit

Fit is, of course, a question of personal preference – but it’s generally best to give yourself some room down there. Excessively tight underwear can lead to chafing or even a sweat rash. Ask yourself, are the bands at the base of the boxers constricting your legs, or are are your underparts considerably roomy? If the former, you probably need to go up a size.

Even if you prefer the look of smaller-style boxers or even jock-style pants, take care that you don’t go too tight. If you need convincing, studies suggest that wearing looser underwear can increase your sperm count. Your men’s boxers should fit perfectly, not just for your comfort, but for your fertility and general health, too.

The Material

There are few things worse than having sweaty nether-regions, right? While we’re not suggesting that you pack an additional pair of men’s boxers in your gym bag exclusively to workout in, picking the right material will elevate your comfort levels in the squat rack and beyond, while keeping chafing to a minimum.

When it comes to picking the best men’s boxers for your workout, cotton is the ideal choice, helping your appendage breathe through a naturally functional fabric. Alternatively, moisture-wicking fabric – think Lululemon's uber-comfy Always in Motion underwear line – is a solid bet. Because uncomfortable boxers are the last thing you want to worry about when you’re counting your reps.

The Colour

Listen, as long as they’re not sludge brown or novelty-printed, you really can’t go too far wrong with the colour of your pants. Navy blue, grey, white, black: take your pick. Black and grey are perhaps the most versatile and long-lasting colours, so if it’s longevity or subtlety you’re after, choose darker shades.

Key Styles


These loose-fitting and light-weight shorts with an elasticated waist. Men’s boxer shorts come in several styles, from cropped and baggy to long and tighter. The classic style offers high-coverage, while trendier low-rise options will give a closer-to-the-body feel. Their biggest strength – that they give your bits room to move – is also their biggest weakness. Fair warning: your junk will be bouncing about like a prize fighter in the early rounds.


Compact and supportive, briefs are the closest underwear gets to that classic Speedo shape. On the plus side, your tackle won’t move around too much. The downside is that, well, you’ll be wearing little pants. And they can take plenty of personality to pull off. However, if you’ve been crushing Leg Day lately and have the quads to show for it, this style will be the most comfortable, since they won’t roll up beneath your trousers.


The hallowed middle ground between boxer and brief. Trunks – which are also called hipsters – are supportive, with longer legs, so you’ll feel less ‘on show’, so to speak, if you’re wearing those and nothing else. They also sit lower on the hips, so you can show off that hard-earned six-pack.

The Waistband

The waistband of your underwear poking out over your jeans was, for a long time, as important to a Saturday night outfit as your Vivienne Westwood shirt being properly ironed. It was a signifier. ‘I wear Calvin Klein underwear. I am sophisticated.’

Prior to that, in the early nineties when jeans were worn bum-cheek low, the right underwear wasn’t so much an item of clothing as an accessory. Old hat or not, there’s no doubt that men still have their ‘best boxers’, the ones they keep for special occasions. And, invariably, they’ll have a designer’s name on their waistband. We say, if wearing them helps you feel 100 per cent, embrace it.

The Best Men's Underwear Brands

Calvin Klein

By sewing his name onto his pants, Calvin Klein made it fashionable to flash your smalls. Having diversified from the world-famous boxers, they now produce briefs, trunks and boxer-briefs in various lengths and fabrications.


When it comes to activewear, Nike's expertise speaks for itself. Effortlessly fusing style and performance, their boxers are both super comfortable for everyday wear and fully equipped to support you through whatever exercise you throw their way.


The people who brought boxer shorts to the UK, Sunspel have been making underwear since 1860. Their boxers are almost identical to the original designs but they’ve done away with the excess fabric so you can wear them under fitted trousers comfortably.

Hugo Boss

German designer label Hugo Boss make their boxers from a cotton and elastane mix that means they’re comfortable to wear and move with your body. Their slim waistband, shallower than their competitors is arguably subtler, too.

Emporio Armani

Every self-respecting fashion-lifestyle brand needs underwear in their stable. Armani is no exception. With their eagle emblazoned across the waistband of your underwear you’re immediately part of the Armani universe.

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