Made-to-measure boxer shorts: the ultimate indulgence, or just a load of pants?

The road of excess, felt William Blake, leads to the palace of wisdom. It’s a line long quoted by hedonists to justify their chronic overindulgence. Shopaholics too. Blake continued, sounding as much like a chastened lottery winner as a visionary Romantic: “You never know what is enough until you know what is more than enough.”

How about monogrammed made-to-measure underpants in a cashmere blend, I wondered to myself on the hottest day of the decade as I stood, trouserless, on the shopfloor of a Marylebone menswear boutique, having my bum tape-measured by a charming man named Nic who was wearing a protective face visor, and frankly who could blame him? Are monogrammed made-to-measure underpants in a cashmere blend more than enough? Only one way, pace London’s great hallucinator, to find out.

Navigated by Uber, my road of excess on this occasion led not to a grand palace of wisdom but rather a modest temple to luxury. Hamilton and Hare is a small but airy shop – blond wood and white-brick walls – on Chiltern Street, the second most important address in London for men’s style snobs after the obvious one that everyone has heard of, even those who have never had anything made-to-measure, let alone their smalls. (I know these people exist; I used to be one myself.)

Confession of chronic overindulgence: I am a man not unaccustomed to being fitted for his clothes. Not that I’ve had much cause to wear them lately, but I own multiple bespoke suits, bespoke blazers, bespoke shirts, bespoke shoes, bespoke spectacles. Even so, until I heard of Hamilton and Hare’s new service – 20 pairs of made-to-measure boxer shorts, from £1,650 – I had not considered consulting a tailor about my unmentionables. Not once in my life had it ever occurred to me to commission my kecks. With what I now can see was quite a stunning lack of imagination I have, for as far back as I can remember, bought my pants from Calvin Klein in packs of three. Not that you really need to know this but I favour a boxer brief, and I’ve always found they do the job tolerably well, being neither too snug nor too roomy, too balmy nor too breezy. They might not look like much – but then, who’s looking? 

Hamilton and Hare was founded in 2012 by Olivia Francis, a former account director at M&C Saatchi, the advertising agency, who spotted a gap in the market for premium men’s underwear. “I really do think underwear is important,” she told me over coffee, once I’d put my trousers back on. “And it just seemed to have been so overlooked. For women there are beautiful brands and stores, and the process of buying underwear is pleasurable. That just didn’t exist for men. So I sat on that for a while,” she continued, no pun intended, “and eventually I was like, ‘I’m going to do it.’”

She started with boxer shorts. “It’s something that literally hadn’t been touched since the 1920s,” she said. “No one had thought about it.” Boxers, she learned from male friends, were often uncomfortable to wear. And they didn’t work with slimmer trousers. With the help of a tailor she came up with a better boxer. “We obsessed over every detail until we got it where we wanted it, but the basic idea was to have a back seam, so it’s constructed more like a trouser rather than the old nappy shape.” 

I don’t think I’ve worn boxer shorts since I was a preteen, trying – tragically – to mimic sexy Nick Kamen in the famous Levi’s laundrette commercial. (Google it, kids.) Why would I wear them now? “Because if you’re wearing a suit, the boxer short has a tailored cut that follows the line of your trousers,” Francis said. “It’s less revealing. And it’s cooler and airier. But a lot of that is fit.”

Hamilton and Hare now also offers boxer briefs – “particularly good under jeans because jeans are quite heavy and boxers tend to get a bit crumpled” – as well as briefs, trunks, sports trunks, pyjamas and “loungewear”. But only the boxers are available made-to-measure. 

To put it bluntly, unless one were in some way misshapen, or really quite spectacularly blessed/cursed, why on earth would a man need made-to-measure underpants? “Why do you need made-to-measure anything?” Francis asked me. “It delivers a better product. My initial brief was ‘How do we make the best boxer short?’ The answer is: you should tailor it to each individual body shape. There are people out there who do have slightly odd body shapes where this is very relevant. So yes, it’s catering for those people. But, also, if you have made-to-measure suits or made-to-measure shoes  – or made-to-measure anything – but your underwear doesn’t fit properly, what’s the point?”

The process is straightforward: I was fitted in a standard pair of H and H boxers (size medium, thanks very much for asking). Nic judged that we should take a little from the seat and shorten the leg just a touch. These changes were noted down by his elegant colleague, Harlee, who was sipping iced coffee through a straw – and, again, who could blame her? 

I stroked swatches, weighing textures and patterns. I went for a combination: 15 pairs of midweight cotton boxers, five each in pale pink, a thin blue stripe, and a bolder blue stripe. Then two sky-blue pairs in a silk-cotton blend for very hot days. Two navy pairs in a super-soft cashmere blend, for winter. And most spoiling of all: a piqué-textured pair in white, for wearing with black tie. If that’s not the definition of lucky pants I don’t know what would be. For buttons: corozo nut, rather than mother-of-pearl. And, yes, my initials to be stitched into one pair of each style, because the editor of this magazine insisted. (Infra dig, I’m afraid. But she’s a bit like that.)

I went back a fortnight later and Nic made further adjustments to a prototype pair he’d had made for me, even though, to my mind, he had achieved perfection at his first attempt. The pants fit like a dream. Some weeks later a large box arrived with my name on it. Too much? More than enough? Or just right?

William Blake, to wrap up this pants story with a pretty bow, was born a short walk from Hamilton and Hare, in the flat above his family’s hosiery shop in Soho. The Blakes sold “wool-knit stockings, caps, vests, wainscots and undergarments for both men and women”: loungewear, avant le lettre. So there’s every chance Blake really did have his pants made-to-measure. I like to think so, anyway. It’s what all we Romantic visionaries do.  

Alex Bilmes is editor-in-chief of Esquire