The SPY Debrief: Menswear Maven Jay Carroll
Our editors independently select the products we recommend. We may earn a commission on items bought through our links.
Where do you land on premium, deftly-branded olive oil? If it’s somewhere close to “Is there another way to live?” then Jay Carroll needs no introduction.
Today's Top Deals
For the rest of you living the Kirkland Signature lifestyle, Jay Carroll is a menswear maven, brand builder, Mainer, and olive oil impresario behind the brand Wonder Valley. You’ll also find him in Joshua Tree and Kyoto throughout the year.
Carroll has spent a career cultivating (and falling prey to) desire. His cool kid IMDB includes stints at Rogue’s Gallery, Levi’s, Hopper Goods, and projects with the Ace Hotel and L.L. Bean. Wonder Valley also makes outstanding skincare products, but that hasn’t stopped Carroll from putting his shaved head down and working out a new skincare brand called Non Finito, which launches later this year.
Here’s Jay on what he buys, why he buys it, and the forever brand he just can’t shake.
What was your first big purchase?
I remember, back when I didn’t have much money, going to Japan and spending way more than I had at Kapital stores. I was working for a small menswear company around 2008 and Kapital just blew my mind. I just got whatever I wanted and put it in the bag. That’s not how I shop at all, but at the time I was like, “So this is what shopping sprees are like.”
What about a recent splurge?
I splurged on a pair of custom boots from Stewart’s Boots in Tucson, AZ. I love that whole process of going to get your feet traced and talking directly with the dude about what you want.
I also recently bought a jacket from Tony Shirtmakers, a local shop in the part of Maine where I was living this winter. We had Tony over to the house and he left his jacket by accident. I was like, Hey I’m gonna get this to you but in the meantime can I take it for a test run? After wearing it for a couple weeks, I had to have it.
What do you collect and why?
I used to collect a lot of stuff, and I’m having a moment where I’m letting go of sentimentality and trying to be present. In both my Maine and Joshua Tree houses, I collect rocks and minerals. I usually take them away from a hike or a moment with a friend. In Maine, I’ll go on a beach hike with a pal or my wife and daughter and I’ll pick up some cool rock to remind me of it.
In the past, I’ve collected rare denim, and since sold it all. I used to have 500 vintage t-shirts. I had a good amount of Native American jewelry for a while too. Now I have just two or three pieces left.
I was borderline a hoarder before. When my wife moved in with me when we lived in San Francisco, she opened up the oven and cabinets and they were filled with Japanese fashion magazines. I had to let it go. Even since I was a kid taking Polaroids and writing letters, sentimentality was in my DNA to a point where I felt like it owned me. And I’ve had to let go over the past 5 years or so.
What will we never catch you spending money on?
Haircuts! I shave my head. I guess streetwear drops. I’m not a drop consumer. I’m never going to buy Chrome Hearts jewelry, I’m never going to own a Cyber Truck. You’ll never catch me with NFTs or bottle service. And I won’t get Botox.
Have you ever shoplifted? If so, what?
When I was probably like 15 or so, do you remember JNCO jeans? Skaters, ravers, and straight edge kids all used to wear these huge jeans. There was a system I learned from a friend of a friend that you could wear a pair of JNCOs you already owned into the dressing room and then put another pair underneath them and walk out.
What’s a purchase you regret making?
I get very into the sensory world of retail, and when it’s done well, I can really be transported by it. And when the retail people have done their jobs really well, I have found myself trying something on in the store that makes me feel like a part of that world. And then you bring it home and wear it and you look like a fucking clown.
I can think of one example at RTH in Palm Springs. He builds a strong world and there were some drop crotch tapered pants that felt right at the time, but wearing them again I’m like what did I do?
What direct-to-consumer ads do your algorithms feed you? Put another way, who does your algorithm think you are? Is it on par with how you think of yourself, or not so much?
The internet thinks I’m someone who is so concerned with their health that they think they’re going to die if they don’t buy every supplement and every pill and work out every day. I’m 44 now and I do go to the gym, but I get hit with all this stuff that says you’re doing it wrong and this is what you need to do to save your life.
If you could be a spokesperson for an existing brand, what would it be and why?
I’m still a Kapital fan. They’ve informed a lot of what I’ve done in my career in menswear. What’s special about them is that they own their own factories and they’re able to produce stuff that felt impossible, from my perspective, to make. I drank the Kool-Aid and I’m still a big fan.
What items do you carry with you every day?
The holy trinity of wallet, phone, and keys. My keys include my truck fob and this old brass cast anchor keychain from my Rogues Gallery days. I have a gorgeous hand-sewn Japanese leather wallet from a guy in Kagoshima Rhythmos.
I also carry water and Jacques Marie Mage sunglasses. I did a collab with them once, maybe 9 years ago when I was working for a brand called Hopper and we did a sunglass called the Taos based on Dennis’s character in Easy Rider.
A.J. Morgan Women's Round Sunglasses
Buy Now On Amazon
This Amazon dupe isn’t a 1-1 with Jacques Marie Mage’s $800 frames, but the thick design and rounded square shape get you close to the aesthetic.
More Top Deals from SPY
Best of SPY
