Men’s Underwear Style Guide



Gone are the days when your only choice in the morning was between your Dad’s old fashioned briefs and the muscle-bound model’s favourite – a boxer short. Now we’ve got trunks, hybrid boxer- briefs and even male thongs! A rainbow of colours greet us in the drawer, skyscraper-style waist sizes from low to high-rise and material choices ranging from Merino wool to “breathable synthetics.” Confused? Us too.

But fear not shoppers, Utility Bear is here to guide you through the basics of the modern man’s undergarment essentials, with everything you need to know but were afraid to ask…

What To Consider Before You Choose Your Underwear

There are lots of things that will dictate your choice of ‘tighty-whiteys’. Whether your size requires support or space, how much movement you do during the day, the types of clothes you wear on the outside, your leg size, waist size and whether or not anyone else will be seeing you without clothes on – lucky bear!

Men’s Underwear Styles

Now you know what you want, you need to know what to ask for:


The original underwear staple cruelly classed as unadventurous due to their fanbase consisting mostly of dads, but do not underestimate the classic cut. Their supportive fit – fully around the back, less around the trunk area – means they don’t move around uncomfortably under your clothes. And they’re usually made of a long-wear material like cotton. Comfort and practicality are not to be sniffed at, but they’re as sexy as a knitted Christmas jumper. Opting for a lower-rise waistband will offer the same support but, added to a darker colour, will up the stakes if you’re looking to impress when you undress!


For those who prefer their fruit ‘hanging loose and swinging low’, these are the traditional male go-to. Pioneered by Jacob Golomb, the founder of boxing equipment company Everlast, he tweaked designs for trunks worn by pugilists to create the “boxer short.” The style rose in popularity not just because they were super-comfortable, but because they marked an adult departure from the briefs boys wore as cubs, often made of silk for real gentleman swagger. A long-cut leg and completely loose style (except at the waistband) this short-style underwear allows for optimum space and temperature – i.e. optimum fertility!


The modern hybrid of old and new changed the game thanks to Calvin Klein’s head of menswear design John Varvatos. The uber brands of the 90s changed underwear from something we hid under our clothes to something we flaunt publicly as part of our outfit. Well, the waistbands at least! They do what they say – support like a brief with extra coverage like a boxer. The benefit is purely aesthetic, with longer leg coverage reducing the geek-factor of the brief with every extra inch of material, as well as the adventurous patterns and colours of the modern branded waistband.


Think boxers with a shorter leg, hipster trunks are like the “hot pants” of the male underwear world: fitted to support and avoid over-movement, with an added sexy-factor thrown in. The fit is based on mid-century swimming trunks, hence the name. Arthur Kneibler, a designer at the Wisconsin hosiery company Coopers Inc., introduced his new kind of legless underwear after seeing an ad for French swimwear. He called it the “Jockey short” because the high level of support was reminiscent of jockstraps. In 1971, the company rebranded as our very own Jockey underwear. With the amount of skin on show, they’re probably best-suited to a more athletic physique though!


With that said, they don’t come as daringly skin-showing as the male thong! Growing in popularity as the boys realise the minimalist benefits of a strap-and-pouch undergarment, especially when the Age of the Skinny Jean dawned, the thong provides comfort and support without the visible lines and often uncomfortable movement of looser styles. They split into two main options – the “T- shape” thong and the thinner “G-string” variety. Not for the faint of heart or low of confidence!


Named for the traditional bikini style, but very different to their female counterpart, these undies provide a modern, complimentary mix between a trunk and a thong – a low waist and very high-cut leg with a fitted front cup that is triangular, like a jockstrap to provide support but with coverage and support at the back too. Bikini bottoms often also come in a waistband-only or a “Tanga” band-side style – allowing for extra leg movement making them a great choice for sports. Overall a simple and practical design, suitable for everyday use.

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