Jimmi Simpson Talks Tailored Clothing and Westworld Predictions 

Spoiler alert: Jimmi Simpson isn’t done with

yet. At least he hopes he isn’t, as do the rest of us, who marveled at his character’s transformation from earnest, rumpled William into series-defining dark cowboy over the course of the show’s hit first season. Luckily, Simpson predicts there’s at least “six or seven” seasons of

,” he told us. And we’ll happily go along for the ride. Not only did

deliver gripping performances—shoutout Evan Rachel Wood—and mind-melting plot twists, it was low-key one of the most stylish shows on television. Nearly every character’s costume in the futuristic Wild West theme park balanced historical accuracy with a pinch of contemporary trendiness. And Simpson’s character wore band-collar shirts, patterned silk scarves, black jeans, and cowboy boots with the best of them.

s Spring fashion portfolio—where he and some of our other favorite guys of the moment rocked the season’s best relaxed tailoring—to discuss what’s next for him, for William, and for his newly reinvigorated personal style. Check it out below, and check out the full shoot here.

I was delighted. It’s some of the work I’m proudest of. A lot of times, I do work either on stage or on small-scale television that a lot of people miss. It’s so nice to feel proud of something that people are engaged in.

Really—it’s so pertinent. We’re dealing with our own waves of revolution. And it was the perfect time for [

writers] Jonah [Nolan] and Lisa [Joy] to talk about it.

was the costume design. From the moment your character, William, arrived on the show by walking into basically a futuristic Tom Ford cowboy store—

It was just gorgeous. The same person that brought the style into that scene was responsible for all the historically accurate style—or intentionally inaccurate style—throughout the whole show, [costume designer] Ane Crabtree. She did every single choice that blew your mind. And it’s because she’s so passionate about it.

Back in the day, they did things a little more fitted than I’m used to doing, and Ane encouraged me to do that in my life and have a little bit more structure in my look. I’ve always been a little bit Western-leaning anyway. Tailoring is something I think most, like, straight men aren’t aware of how amazing the effect is. Especially being a skinny guy. We learned from the baggy ’90s situation, where the idea was you’re thin, so surround yourself in fabric. But as I got older, I realized—when you cut the fabric away, you stop looking so skinny!

Sure, and now that dress codes are relaxing, wearing one is a much more conscious choice.

Oh, it’s so true. I guess that’s why they’re looking sharper. The suit now is less a uniform that you’re putting on to go to school and it’s a choice, a choice to look better, as opposed to looking how you have to look.

It would be helpful if I did. I think I’ve gotten most from the activity I’m doing, which is generally skateboarding. It’s about simplicity, and layers, and comfort. I think a well-fit T-shirt and jeans can just kill, style-wise. At least that’s what I tell myself, because that’s what I’m going to keep wearing till I die.

I mean, I’m 41, so I moved to the longboard when I hit 30, but it’s a lifesaver. Not only does it eclipse my time for parking in Los Angeles, because I keep my skateboard in my trunk at all times, but it helps me feel kind of young. I’ve skateboarded my whole life, and I’m going to keep enjoying it until my age prohibits me. My buddies who play golf, it seems to me a very passive choice of like,

I’m old, I’m tired, and this is now my time where I don’t have to talk to anybody.

“No matter which job you’re doing in acting, you have to be doing something different, or else you’re not doing your job.”

What’s your next project? I just wrapped David Robert Mitchell’s movie

, and he’s written this 150-page opus to L.A., and he’s fabricated this entire history and it’s fabulous, and Andrew Garfield’s our lead and he’s so talented.

It’s all its own art form, each one. I do a lot of theater, a lot of television, a lot of film. Even more than the medium, I think it’s project-specific as to how your craft changes. But it’s always different. And that’s one of the reasons I fell for this career, is because no matter which job you’re doing in acting, you have to be doing something different or else you’re not doing your job, basically. So it’s always new, and I personally get off on things being new and fresh. You always have to be pushing your boundaries. I try to avoid doing long-term roles that don’t grow or change. I’ve been in this business for 20 years, and I haven’t had a long-running sitcom or anything that’s a little more technical, because I think I’d start to lose my shit.

season two and beyond. What do you know about your potential involvement?

So far, my involvement in that is unclear. If they have more for William, I would assume it would be a whole new kind of story. Because I feel like this story, the love affair [with Evan Rachel Wood’s character, Dolores], we know everything, we know what happens, we don’t have to belabor that point. But if they have a reason—I mean, it was the greatest set I’ve ever worked on. But we’re all speculating what season two will be, and I think it’ll be something that will blow our minds, to the degree that the first season did. But I wouldn’t be surprised if William showed up season three or something.

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