Which is the most comfortable brand of underwear men?

If you're anything like me, you probably don't buy new underwear as often as you should. (I've pushed my undies to the limit in recent years, retiring them only when the waistbands detach or holes appear.) 

But to the rest of the world, men's underwear has become a hot fashion commodity. Streetwear behemoth Supreme released boxer briefs in one of its unannounced drops – a four-pack costs about $100 from online re-sellers. Then Virgil Abloh's mighty Off-White issued cotton boxers at the frankly ludicrous price of $230 for a single pair.

Traditional underwear manufacturers have started to release limited editions and luxury versions, too: British heritage brand Sunspel recently launched cotton trunks "made from rare Sea Island cotton for ultimate softness" that retail for over $100. Then, of course, there's Calvin Klein, whose new customisable #MYCALVINS retail at $60 each.

Tom Ford enters the fray

The latest competitor in the men's underwear space is Tom Ford, whose new range is available in Australia exclusively via Harrolds. Like Mr Ford's suiting, the underwear is ambitiously priced: a pair of basic boxer briefs costs $99 while the silk boxer shorts are an eye-watering $219. 

In addition to plain colourways, both the boxer briefs and the boxers are available with cheeky zebra-stripe and leopard-spot prints. There's also a rather strange-looking 'metallic cotton' boxer brief that glimmers in the light.

Curiosity got the better of me, so I decided to pick up a pair of Tom Ford's boxer briefs and test-drive them. For comparison's sake, I also acquired the latest boxer-brief styles from my usual brands, Calvin Klein and Bonds.

La dolce vita

The first thing I noticed about the Tom Ford boxer briefs was the quality of the cotton. The material itself is thicker and sturdier than is usual for a pair of boxer briefs, but the weave is incredibly fine, allowing for good movement. Checking the tag, I wasn't surprised to see that the underwear was manufactured in Italy.

Over the course of a busy day in Sydney, the Tom Fords were unobtrusive and comfortable. Importantly, there was minimal ride-up and little need for re-adjustment. 

They won't be to everybody's taste: there is just five per cent elastane in the Tom Ford material (many other brands now include eight per cent to 10 per cent) which means the underwear is less clingy and stretchy than some of its competitors.  


But the quality of these jocks is undeniable. Judging by the construction, I imagine they'll be in my underwear rotation for years to come.

Revisiting the classics

The next pair of undies I grabbed was the cotton stretch trunk by Calvin Klein ($49.95). It's been a while since I've purchased CK underwear, and I was surprised by how much elastane this style contained (nine per cent). The elastane, combined with the overall thinness of the fabric, gave the trunks a 'barely there' feel during my test-drive, but made me wonder how the underwear would fare over the course of a long day or an international flight.

I also picked up a pair of Bonds' new X-Temp trunks ($24.95), which apparently help regulate body temperature and evaporate sweat quickly. Those assets weren't apparent to me, but I was impressed by the quality of the X-Temp's construction: the waistband was strong and the cotton weave struck a good balance between protection and breathability. Noteworthy were the thick, elasticated leg bands, which took some getting used to but completely eliminated ride-up.

Reaching a verdict

None of the underwear I tried was defective in any way and choosing a winner is really a matter of personal preference. I found the Calvin Kleins the most comfortable and, if I were still single, would feel good about wearing them on a date. The Bonds seemed exceptionally well made for the price and would be ideal for the gym. And the Tom Fords exuded sophistication and quality.

Would I buy more pairs of Tom Ford's $100 underwear? If I could afford them, yes. But the alternatives aren't too shabby, either.

Dan's writing on style, travel and more has appeared in The New York Times, the Australian Financial Review, Condé Nast Traveller and others. He is based in Sydney.

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