It’s hard to believe it’s been ten years since we opened the doors at Tailors’ Keep. When I look back, it’s wild to think how far we’ve come—especially considering how it all started.

I’ve been obsessed with clothing for as long as I can remember. As a kid, I spent hours in mall stores, picking apart why one shirt fit better than another, why a t-shirt from one brand hung just right and another didn’t. At the time, I didn’t think much of it—I just wanted to spend time in those spaces. But looking back, my obsession with detail was already taking root.

Fast forward a bit, and I found myself working retail jobs—Banana Republic first, then J.Crew—learning everything I could about merchandising and fit. It was while working at J.Crew that I met my first tailoring mentor. I asked if he’d take on an apprentice, and he said he’d been waiting for someone to ask for the last ten years. That was it. I dove headfirst into learning the craft. No shortcuts. No corporate ladder. Just hands-on, needle-and-thread, figure-it-out-from-the-ground-up work.

By 2012, I was in San Francisco, working in custom suiting. Three years later, I took a deep breath and started Tailors’ Keep. No investors. Not much of a safety net. Just a few loyal clients and a belief that if we focused on doing the work really well, people would find us.

At the start, we were scrappy. We did it all—alterations, custom suiting, anything to keep the lights on. Alterations got us through those early days. People trusted us because we cared about the details, whether it was hemming their jeans or remaking a jacket. It wasn’t the most scalable business, but it was what we needed to build trust.

Then the pandemic hit. It forced a hard reset. I had to ask myself: who do I want Tailors’ Keep to be on the other side of this? The answer: a company that does one thing really, really well—tailoring.

That’s when our tailors and I reached a point where we could fully embrace our in-house bespoke program. It’s something I’m deeply proud of. A fully bespoke garment is a true investment—of time, cost, and care—and we wanted to honor that by doing it the right way, every time.

At the same time, we reimagined our semi-bespoke offering by partnering with new makers whose work not only matched our standards, but in many ways exceeded them. Today, our semi-bespoke garments are 90% made by hand, and the quality-to-value ratio is something I stand behind without hesitation.

Now, every garment we make—bespoke or semi—is the best it’s ever been.

What sets us apart isn’t just the clothing. It’s the experience. In a world where you can buy anything with two clicks and have it show up the same day, we offer something different. A place where you can slow down, have a drink, talk cloth and fit, and build something personal.

Over the years, we have built an exceptional team and they make Tailors’ Keep what it is. Everyone has a clear role, and they’re damn good at what they do. The front-of-house team sets the tone, making sure every client feels welcomed, understood, and confident from the moment they walk in. Our fitters know their craft—translating someone’s vision into a garment that fits and feels exactly right. Behind the scenes, our back-of-house team keeps everything running smoothly, managing the details, timelines, and logistics that make the whole process work. It’s not effortless—but it’s thoughtful, deliberate, and focused on giving each client an experience that feels seamless from start to finish.

Some of our clients have been with us since day one. Watching them evolve, watching their style grow along with ours—that has been something truly special. One of them even painted an abstract piece for our Palo Alto shop. Another has sent so many people our way over the years that I’ve lost count. These relationships are the backbone of Tailors’ Keep.

And looking ahead, we’re focused on refining and growing—dialing in our process, expanding our offerings, and continuing to make the customer experience as exceptional as the clothing itself. We’re working on a denim ready-to-wear line, along with some other really cool things that I’m not quite ready to share yet.

To mark this milestone, we’re hosting a celebration—and we’d love to see you there. Join us on Friday, December 12th, for an evening of good drinks, good conversation, and ten years of Tailors’ Keep. It’s our way of saying thank you to the clients, collaborators, and friends who’ve helped shape the last decade. Details to follow, but for now, save the date.

Friends often ask what it’s been like, or if I have any advice for someone just starting out—whether it’s in a career or building something of their own. If I’ve learned anything over the last ten years, it’s this: stick with it. The early years are tough. You’ll question yourself, you’ll wonder if it’s worth it, and there will be moments when walking away feels like the easier option. But if you keep showing up, keep learning, and commit to getting really good at what you do, people will find you. And they’ll stick with you.

I’m a father now and I think about the lessons I want to pass on to my son. Patience, consistency, and doing the hard work, even when no one’s watching, have gotten me through the last decade. I have a feeling they’ll serve him well too.

At Tailors’ Keep, I have always believed that quality matters. Ten years in, we believe it even more. 

Here’s to the next decade.

- Ryan