Tailor’s Keep

Made by hand in San Francisco.

Often, we can’t help but consider how we would do things if we had the space, the resources, or the freedom to make exactly what we want. We all know these options exist, but for whatever reason, they go unacted on. Over several months, Tailor’s Keep in San Francisco made a jacket in that spirit — a one-of-one, just for me. It was an emotional affair on many levels: to see such a pure expression of craft, to bond again with the city of San Francisco, and to revitalize a wardrobe devastated by things beyond my control. What started as simply a nice jacket ended in connections I will forever cherish and a piece of clothing I will always own.

Good tailoring benefits from planning ahead. When you take the time to find the right fit and think carefully about what your wardrobe is missing, you can make decisions with a clear, unhurried head. After commissioning a jacket with Tailor’s Keep, I saw a wonderful expression of all of these concepts take physical form.

If you are like me, you spend a lot of time thinking about the perfect thing. The focus of our wardrobes evolves around that idea once the foundation is in place. We obsess over the jacket that’s just right for that short sliver of spring. We look for the perfect shoes for a specific event, or the very particular bag suited to one type of outing. What if something specific was the perfect thing because it was made just for you — and with versatility in mind? That’s what I set out to do with Tailor’s Keep. I wanted something made for me, and I wanted to be able to wear it constantly.

There’s a lot to consider when commissioning a bespoke jacket. It’s a big commitment on many levels, but it also forces you to think deeply about what you really want from your clothing. My journey started mid-year when I flew to SF to select fabrics, have an initial fitting, and begin a process that would become one of the best clothing acquisitions I have ever made.

There are people far more knowledgeable about tailored clothing than I am — Coggins is one of them, as are Simon Crompton, Jeremy Kirkland, and of course Derek Guy. Though I do have a solid understanding of how things are made and what makes something good, my focus has always been elsewhere: what makes the people behind a brand worth supporting. Trust in people and they will deliver you quality. When people you believe in make something you love, it gives the garment soul. This is what elevates a jacket — a deep connection that transcends the mere buying of clothes.

Tailor’s Keep makes bespoke garments by hand in their small workshop in the Jackson Square neighborhood of San Francisco. It’s a one-of-one artisan operation in the workrooms above their beautiful shop, in the shadow of the Transamerica building. Ryan Devens started Tailor’s Keep in 2015 with money from his savings. I marvel at endeavors like this because it runs against the conventional wisdom of modern entrepreneurship — especially in a city like San Francisco. Ryan had a vision and a passion for clothing, which is the only way something like this could work. Over the years, Tailor’s Keep has gained a committed following through both a refined point of view and a commitment to craft. A small team of master craftspeople work a few floors above the shop, where bespoke garments are made entirely by hand — from measurements to paper patterns to finished pieces, all in the same room. It’s an incredible commitment to the purest form of tailoring.

When I met Ryan for the first time, I had so many questions. How did you end up doing this? What gave you the idea it could work? How have you made it to ten years? The story is fairly straightforward. Ryan loved tailoring and wanted to do something ambitious. He doesn’t seem daunted by challenges or obstacles — he studies them meticulously and systematically works through each problem until he has mastered the medium. I saw this in several areas of Tailor’s Keep. The way he dove into photography is one example, driven by curiosity and a love of equipment. It’s happening now with denim as he works on making jeans. He doesn’t seem intimidated by these ideas, and I think that’s exactly what has driven him to build Tailor’s Keep over the past decade.

I genuinely love this kind of stubborn ambition. Tailor’s Keep is the sort of thing I imagine people probably tried to talk Ryan out of. “There’s no way a bespoke tailor succeeds in San Francisco,” they might have said. But through his dedication to the vision, he built a steady clientele and a real business. He is doing things exactly the way he wanted, and to me, that’s inspiring.

At the beginning of the process, you think conceptually about what you want — the fabric, the details. I wanted a sport coat I could wear in California, but also in New York or Scotland. I landed on a beautiful Glen Plaid cloth from Fox Brothers Flannels in England. It’s a timeless pattern in a beautiful color. I wanted patch pockets and a decently wide lapel. Over the course of two more fittings, you could see the layers of the jacket coming together — first with no sleeves, then at the final appointment, one sleeve on and one to be finished that same day.

I don’t wear many suits, but I find myself reaching for sport coats with denim constantly. I love that pairing and it was the inspiration for this commission. I wanted something softer than the tweed I’d had made recently, and it was hard to resist this wool from Fox Flannels.

Having this jacked made for me took longer than it might for someone local or more flexibility in their schedule. I spaced my trips out by several months, working around other things in my life, and there was no pressure to rush. Part of the point was spending time in San Francisco. Every return visit was a genuine delight. I drank wine at Verjus, shopped at Cable Car Clothiers, Presidio Post, and Lost Coast Outfitters, and had coffee at The Coffee Movement. I went into each trip with so much positive anticipation it was hard not to enjoy every minute of it.

When I arrived for my third and final fitting, it was an early autumn morning. I took the first flight in and San Francisco was just waking up as I arrived. As I made my way to Jackson Square there was a chill in the air —sport coat weather I thought— and I knew that by sunset I would be wearing my new jacket.

As I walked up to Tailor’s Keep, Ryan Devens was standing on the sidewalk in front of one of his two storefronts on Washington Street. In his hands was my jacket, its Glen Check pattern distinct even from a distance. The jacket was missing one sleeve, and Ryan was carrying it down from the workshop upstairs to check the fit before the last arm was sewn on. It occurred to me in that moment that this is how the jacket travels at Tailor’s Keep. There’s no complex logistics operation — someone just carries it downstairs, in their hands, unwrapped. It’s a way of working that, in addition to being hyper-local, isn’t seen much anymore because it’s considered too impractical.

There’s a lot of talk about what you would do if you lost all of your possessions. The optimistic take is that you’d have a fresh start — a chance to build a wardrobe with the clarity of style that’s been refined over time. That’s the conventional wisdom, but I’m here to say it doesn’t really work out that way. Having this jacket made for me was a realization that certain items just mean more.

Some of the things we own represent a time or a place that can’t be recreated. Some clothing has more soul than others, and when it’s gone, it feels like a piece of you is missing too. Making this jacket was an undertaking, and it is forever linked to the friends I made in SF along the way. Every time I wear it I will think about those trips — the fittings with Ryan and Tim, the martinis and steak at Harris’, the burgers at Sam’s, the guys in the shop and all of the work done by hand. The process shapes the experience. It elevates a simple piece of clothing into something that becomes truly part of you.