Chaps, be honest. Have you achieved nether-region nirvana? Twenty years ago I had reached the summit of underwear style and comfort but was haunted by the fear that one day I would come crashing down from these Elysian heights. My brand would go out of business and I would be confronting knicker nemesis. And sure enough, a while ago my fashionista friend Kitty Go duly reported that Regatta of Manila, purveyor of the world’s most fabulous baggy boxers in the jauntiest fabrics, was no more. The crisis had struck.
Let’s waste no time on jockeys, Y-fronts, briefs or those execrable jersey cotton hybrids or clingy lycra atrocities beloved by the clueless young. No, when a man is north of 40, he needs the tried and tested boxer short, named (so Shaun Cole’s The Story of Men’s Underwear tells me) after the heavyweight boxer Jack Dempsey, who won the 1919 world title in a pair of long loose shorts.
The best boxers provide support while allowing free movement and a spot of ventilation across the undercarriage. It’s all in the gusset. My design guru friend Stephen Bayley, a boxers man too, says: ‘Infrastructure is at least as important in building design as architecture. If the plumbing and underpinning don’t work, no amount of surface finery will compensate. It’s the same with getting dressed. The psychological advantages of wearing good socks and good underwear are truly profound. You will never achieve firmness and delight in plebeian Y-fronts or suffocating Lycra containers branded with the name of a has-been designer. When I step into my Brooks Brothers boxers I feel immediately dignified. I like my infrastructure to be Ivy League.’
I know what he means. I have tried popular brands like M&S, Boden, Gap and J. Crew but have always been left unsatisfied. Time to up the ante. Men’s underwear is too frivolous not to take seriously.
For a month now I have road-tested some of the finest boxers in Britain. I have walked my dog in Norfolk’s harshest mountain ranges, crossed deserts, sashayed through warzones and boulevardiered through the capital in a range of boxers to bring you this distillation of underwear wisdom.
My man in Budd, shirtmakers to the cognoscenti, kicks off with two models. One is nicknamed the Chairman’s Briefs (£55), the other is known informally as the Buckingham Palace. ‘They have the biggest ballroom in London.’ I can attest to that. Both are fantastic. Derek Rose offers astonishingly luxurious silk boxers (£130), which had me begging for more. Their cotton counterparts (£35) are also excellent. Both score highly for having buttons on the waistband. A man likes to be undone from time to time.
Turnbull & Asser are shirtmakers to the Prince of Wales. Who knows whether they also provide him with boxers to house the crown jewels, but their Sea Island Cotton boxers (£70) offer royal levels of indulgence. Standard cotton is £50. These are among the roomiest here, with shades of Stanley Matthews bagginess circa 1953.
Honourable mentions go to the sumptuously Swiss underwear maestros Zimmerli (€54), Jermyn Street shirtmaker Harvie and Hudson (£30), Hamilton and Hare, who offer a thrilling, very athletic take on the boxer (£32), Burtonwode (£24) and Beaufort & Blake (£20). Boxer bliss achieved.
Subscribe to The Spectator Australia today for a quality of argument not found in any other publication. Subscribe – Try a month free