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Custom-Made Boxers

In the very particular world of bespoke tailoring, are custom boxers the ultimate in understatement or pure folly?

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I don’t spend a lot of time thinking about men’s underpants. And my past attempts to learn more about the subject, say, in the locker room, have often ended in awkward misunderstandings. Still, at a moment when Wall Street bankers are busier justifying their paychecks than spending them, ordering some handmade boxer shorts seems like a stealthy way to indulge one’s itch for luxury without attracting the type of scorn that’s heaped on conspicuous consumers in these uncertain economic times.

And uncertain they are—particularly in Underwearland, where a closely watched economic indicator known as the men’s underwear index (MUI) is down. The idea is that the state of the economy can be tracked through the purchase of men’s underwear: When things are really tough, men cut back even on the true essentials. Last year the MUI fell roughly 2 percent, according to Mintel, a leading market research company, and while the forecast is slightly better for this year, we are clearly in need of an underwear bailout.

So how does even the most unrepentant dandy rationalize committing precious capital to underpants that can run up to $400? “The basic reason is comfort,” says Alexander Kabbaz, an East Hampton–based shirtmaker who also makes 50 to 60 pairs of underwear a year for clients who include a prominent Washington, D.C., lobbyist, a famous novelist, and the CEO of a leading Wall Street firm. (An interesting and telling aside: Private tailors, always reluctant to disclose client information, refused to divulge the names of those who indulge in custom boxers. And when we conducted an informal poll of bespoke fanatics—a few whom we strongly suspect tailor every single item they put on—not one would confess to the practice.)

Still, small though it may be, there is a market. Kabbaz is not alone. A handful of haberdashers—Anto, Brioni, Lorenzini, Turnbull & Asser—offer different grades of custom underwear. For Beverly Hills–based Anto, known as the shirtmaker to the stars, the typical bespoke boxer client is someone who already has his shirts made by the firm.

The amount of workmanship that goes into each pair varies, ranging from a “stock special” (a standard-issue boxer altered to the client’s measurements) to a true bespoke garment. The latter involves multiple measurements to create a pattern of the client’s torso. Kabbaz’s process is intricate and indicative of how to make a truly bespoke pair of shorts. After a first fitting he will produce a batiste—a slightly loose rough draft of the final boxer that the client models at the next meeting, at which time Kabbaz refines the design. He asks the client to return in a week to try on a nearly finished version. Kabbaz then sends him out to wear that garment for a day before producing the final order, which generally takes three to four weeks.

“I want my customers to give me notes and criticisms. Some aspects of the fit depend on their lifestyle. How active? How sedentary? Do they have a tennis player’s walk? If they have a wedgie after a day of sitting, I want to know that,” says Kabbaz, who was a graphic designer, an engineer, and the founder of a disco magazine before buying a company called Pec & Co., whose owner cut shirts in the seventies.

Just as suits come with double or single vents or none at all, there are a few boxer styles beyond the traditional straight-front, elastic waist. The most elaborate is the French, with a quilt-like panel around the waist, mother-of-pearl buttons, and an indent along the back—similar to what you’d see on the back of a Savile Row trouser. In my twenties I roomed with a recreational underwear abuser who would break out a pair from Brooks Brothers whenever he had a big date. They had a small silk bow on the back. He called them his “Frenchies” and thought those fancy pants made him look like Sean Connery in Dr. No. To me he resembled a male cancan dancer. A less foppish yet elegant model is a flat front with no elastic waistband, just side tabs. And finally there is the simple traditional style.

One of the first details any guy stepping into his first custom traditional boxers will notice is the waistband. Instead of elastic chafing against your skin, there’s pleated fabric running around the length of the waist. Another comforting detail: Side vents on the thigh let you sit down without your shorts riding up.

Aside from the workmanship, the biggest factor in determining the price is fabric, with Sea Island cotton being one of the most expensive. The final decision is where to place the monogram (the usual spot is over the left thigh). Ever since I had my first bespoke piece made, I’ve had a love-hate relationship with monograms. My feeling is that the way clothes are cut should be on display without any monument to ego or income. So I asked Jack Sepetjian, who owns Anto with his brother Ken and makes my shirts for me, to put my monogram on my shirttail. That way only my wife would see it. Jack agreed and let me bask in this romantic notion for a minute before informing me he had another client who used the same placement: a studio executive whose claim to fame was being linked to a famous Hollywood madam. We did not discuss that man’s choice in underwear.

The Boxer Briefs

A lot of shirtmakers claim to offer bespoke boxers, but what they are really selling are “stock specials,” or customized versions of ready-to-wear models. True bespoke shorts often require several fittings and are assembled from the resulting pattern.


True bespoke. Hollywood’s favorite shirtmaker requires two fittings to get its clients’ boxers tailored perfectly. From $125;


The fashion house offers a traditional style that can be customized using fabrics from its Reale collection, which includes about 250 swatches made from West Indies Sea Island cotton. From $340;

Kabbaz-Kelly Custom Clothiers

These boxers involve two to three fittings. East Hampton–based Alexander Kabbaz asks new clients to spend a day wearing a rough-draft version of their future boxers and provide him with notes before he makes their first pair. From $250, with a first-order minimum of six pairs;


The family-owned Italian shirtmaker offers both made-to-measure and bespoke boxers that come with a waistband featuring two mother-of-pearl buttons for easy adjustment. Its off-the-rack offerings are sold at Barneys in packs of three. From $200;

Turnbull & Asser

The official tailor to the future king of England does a very comfortable made-to-measure short, thanks to a wedgie-defying wishbone seam on the back. Our “Does Prince Charles or doesn’t he” custom boxer query was met with a stony “No comment.” From $110;


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