There comes a time in every man's life when you have to ask yourself:

Should I be investing in designer boxers?

Maybe you're sick of replacing cheap boxer shorts every few months. Or maybe you just want to impress a certain someone. Either way, there is a wealth of options out there for the more discerning gent.

Every fashion house produces its own range of underwear, at a number of different price points. And then there are the underwear specialists.

Expect to pay upwards of £100 for a single pair by Thom Browne, Zimmerli or Derek Rose. While it may seem crazy to spend so much on a pair of pants, there is clearly no shortage of demand.

Designer boxers are made from higher quality, and therefore more expensive, cuts of fabric. As well as providing a better weave, all named brands will have been thoroughly road-tested to ensure they conform to every body shape. 

And while boxers are always a favourite, you could also experiment with trunks, boxer-briefs, Y-fronts, and more.

Read on for our essential guide to men's designer boxer shorts…

Accessible luxury

+ Best brand: Ralph Lauren

You don't have to spend a fortune to feel the benefits of designer boxer shorts. Just look for lightweight fabrics made with natural fibres (such as cotton) and a range of different fits, which suggests that they have been modelled for a variety of body shapes.Nevertheless, you should expect to spend at least £30 for a pack of good underwear that will last the test of time.

Sporty fit

+ Best brand: Bjorn Borg

Sports underwear is the perfect pick for men on the move. Ergonomically designed, they should be exercise-proof (i.e. sweat-proof) and fitted with a tighter weave of fabric that stays where it is supposed to. And keeps everything else where it's supposed to be…

Classic design

+ Best brand: Hugo Boss

The brand-stamped waistband has become a staple of boxer design over the past few decades after the Calvin Klein underwear collection was launched. And if it ain't broke, why fix it? Mix up these classic designs by investing in a range of colours and stick with high-quality fabrics that combine breathability, insulation, and supreme comfort.


+ Best brand: Diesel

Like it or not, athleisure is definitely a 'thing' now. It basically refers to sportswear that isn't really meant to be used for sports - so, breathable fabrics, with an overall emphasis on style. Look for high street brands such as Diesel, who have begun to offer hi-tech underwear that still looks stylish.

Fashion forward

+ Best brand: Paul Smith

If you're bored of the usual white, grey or black underwear options, designer boxer shorts are a great way to mix up your style. Look for bright colours and unusual prints, which don’t compromise on comfort.


+ Best brand: Tommy Hilfiger

Calvin Klein, Tommy Hilfiger and Ralph Lauren have revolutionised the world of designer underwear. And their tighter-fitting boxers, visible waistband, and high-end fabrics still typify the American aesthetic. Stock up during your next trip to the US, or invest in a multi-pack.


+ Best brand: Ted Baker

If you really want to push the boat out, there are a number of high-end designer options out there to choose from. Menswear genius Tom Ford is launching his first underwear range this year – expect it to sell out fast, regardless of the price tag. In the meantime, look for classically-cut single pairs of boxers by British brands such as Ted Baker.