TK: You’ve got a distinct point of view when it comes to style. Going into this suit with Tailors’ Keep, did you already have a vision for it?
JO: Yeah, Ryan and I were on the same page right away. We both love vintage—whether it’s cars, clothes, jewelry, suitcases. We wanted something that nodded to the 60s and 70s but also felt unique and experimental. That’s where you get details like the belted back vent or the exaggerated lapels and flared trousers. It’s a blend of safari and tailoring—a little unexpected, but it all comes together.
TK: A lot of people still associate custom suiting with formality—think Savile Row, wedding tuxedos, corporate uniforms. But you’ve always worn tailoring in a much more relaxed way.
JO: Totally. Growing up, I thought of suits as something for funerals or business meetings—never something you wore just because you wanted to look good. But when I started diving into vintage style, I realized how casually people used to wear tailoring. People dressed with intention, even to go to the grocery store. That’s what I love. Suits don’t need to be so serious.
TK: Who’s inspiring you style-wise right now?
JO: I pull a lot from the past—Paul Newman, Steve McQueen, Sinatra—but I also love what Leon Bridges is doing. He mixes vintage pieces in such a fresh way. And then there are little things: old posters, old Levi’s ads, even how they used to design luggage or cars. There was a sense of craftsmanship, of personality, that’s harder to find today. I want to bring some of that back with how I dress—and now with the pieces I’m working on for my own line.
TK: Last one—what’s on your playlist right now?
JO: Leon Bridges, of course. Duran Jones and the Indications are big for me. And honestly? A lot of 2000s R&B. Usher, Mario, a little Ludacris. It’s just good vibes.
Our Locations
San Francisco
Our San Francisco showrooms are nestled at the crux of an eclectic mixture of Jackson Square, the Financial District, North Beach, and Chinatown.
This showroom is appointment-only.
Palo Alto
Our newest showroom in Palo Alto opened in 2023, and is tucked away at 433 Hamilton Avenue.
This location is appointment-only.