Finding Keepers: San Francisco Bespoke

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I admit to having some prejudices when it comes to tailoring. For years, I believed the best work is done by old men who have a no-nonsense approach to their craft. In the forward to Anderson & Sheppard’s vanity book, A Style is Born, Graydon Carter describes the Savile Row tailoring shop as a dark, intimidating place. Worn wooden floorboards, ancient tables with heavy rolls of wools and tweeds, and a chest-high etched-glass divider where the front of house would take your order. Even Carter’s description of his cutter, the famous Mr. Norman Halsey, is comically cold:

A few years after we had gotten to know each other, I suggested that he call me Graydon rather than “Mr. Carter.” “Of course, Mr. Carter,” he replied. On occasion, I would try to get him to make something outside the mould, something a bit dramatic, to which he would say “A most daring idea, sir,” and the plan would be quietly dropped. During one fitting, when I felt I had put on a bit of weight, I asked Mr. Halsey if he could cut it so the extra pounds wouldn’t show. “We’re only tailors, sir,” he replied politely, but firmly. 

In the world of bespoke tailoring, you’ll find hundreds of little stories like these. All charming – such as the one of gruff Neapolitan tailors offering clients coffee (I once wrote a two-part follow-up at StyleForum) – but they also contribute to this idea that there are prima facia conditions for a tailoring house to be taken seriously. Things that position the house as genuinely inclined to the craft, rather than a slick facade that’s more about marketing than good work. 

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On that, Tailor’s Keep in San Francisco is exactly the kind of business I would have traditionally ignored in the past. The shop’s owner, Ryan Devens, is a charming young American, not some old Italian maestro. And his shop is tidy and clean with quaint furnishings, rather than dusty and cluttered. There’s a large leather couch sitting across from a small coffee table holding swatch books, then some brass-and-wood shelves nearby holding whiskey. The fitting room is upstairs, where Ryan also keeps his bike. The place feels friendly, young, and inviting – which is exactly the sort of environment that would have turned me away two years ago for no other reason than snobbery. 

Last year, however, my friend Peter wound up with a really nice pair of Tailor’s Keep trousers. Impressed with the work, I gave the shop a call one night. I was actually a bit frustrated that day with an order I received from an overseas Italian tailor – six pairs of bespoke trousers, which took three years to deliver and a bit of back-and-forth for adjustments. In the end, they didn’t even fit as well as my ready-to-wear pants. I didn’t want to send them back to Italy, so I needed someone local for alterations. 

The thing that sold me on Tailor’s Keep is Ryan’s honesty, forthrightness, and intimate knowledge of his work. I described to him my problem with the pants, and he reiterated the same solution Edwin DeBoise explained to me a month prior (Edwin is a great bespoke tailor, but he doesn’t take outside alteration work). Impressed with his answers, I stopped by Ryan’s shop two weeks later. 

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Tailor’s Keep doesn’t have a house style, but a lot of their work tends to be slim and slightly fashionable. Most of the clients here are young, often men looking for a wedding suit, and they typically opt for the made-to-measure program. Ryan makes no qualms about how he uses a Chinese factory – again, a level of forthrightness that I appreciate – and will talk about why he thinks the work is good (as well as the limitations). 

He also has a in-house bespoke service, where a tailor upstairs will draft and cut a personalized pattern from scratch. And if you ask, he can make you something more classically fitting. That’s what I choose. For my first order, I gave Ryan three pairs of trousers to alter – slimming a pair from Steed, then fixing the back balance on some trousers from Salvatore Ambrosi and Napolisumisura. We agreed that, if the alterations turned out well, we could use them as fitting pairs for my bespoke pattern. 

From my experience, the hardest thing to get right on trousers is the back balance. If the trousers are too long or short in the back, you’ll get ripples under the seat or along the back of the thigh. Most men never realize this because you need a proper three-way mirror to see how the trousers fit. You can’t just crane your body because doing so will affect how the trousers look. Add to this the nuances for how the back rise should be cut – the shape of your seat, as well as your natural posture – and you’ll find that you need an experienced tailor to get things right. 

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In that regard, Tailor’s Keep is fantastic. Ryan altered my three pairs perfectly, then we went ahead with a bespoke order, which turned out equally well. The best part is Ryan’s ability to produce something classically fitting, but slim, and have things drape cleanly around the back. No rippling, puckering, or excess fabric – just a clean line from the top of the waistband down to the hem. Ryan isn’t a cutter, but he has extensive experience as a fitter, having worked for a tailor in Nashville before opening his own shop. 

Tailor’s Keep can also finish trousers with any level of handwork. We went with the full monty on this order – decorative handsewn topstitching along the side seams, a handsewn waistband, handsewn buttonholes, and handsewn crows-feet buttons. The work is as good as anything I’ve gotten from Naples. 

If I had to criticize anything, it would be the hips are slightly tight. You can see the issue on Peter’s pants below, where the side pockets slightly gape. That said, it’s an easy enough problem to fix. And if you get trousers with side seams that follow the pockets, like I do these days, the problem is somewhat mitigated.

If you’re in or around San Francisco, and interested in bespoke trousers, I heartily recommend Tailor’s Keep. Personally tailored trousers can be absurdly expensive these days – upwards of $2,000 per pair on Savile Row. Tailor’s Keep is a small fraction of that price, especially if you forgo the handwork, and Ryan is incredibly detail orientated. No, he’s not an old Italian maestro or a British cutter in a three-piece, but he produces excellent work. A reminder that people should be taken on their merits. For all the tailors I’ve tried around the world for trousers, I’m happy to find my favorite one is about thirty minutes from my home. 

(photos via Tailor’s Keep and Peter)

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