Some people are lucky enough to be in the right place at the right time. Others have a hand in making that time and place the right ones. Chase Winfrey (Instagram: @chasehwinner) falls into the latter category. At only 25 years old, the Ohioan-turned-New Yorker is proving why he is one of the leading young voices in classic menswear in New York, and a torchbearer for the next generation of Ivy enthusiasts. Winfrey has a fascinating background with eclectic influences and a resumé that colleagues twice his age would vie for.
Ivy Style caught up with Chase to find out more about the man and the many projects he’s had his hand in. — TREVOR JONES
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Ivy Style: How did your home in Ohio influence you and your outlook on clothes?
Chase Winfrey: Ohio certainly isn’t a hotbed of menswear. There are a few great small shops across the state, though, one of which I was lucky to work at while I was in school. It was a great experience working with brands like Gitman, Southwick, and Alden. Overall, there’s definitely a certain Midwestern attitude, and I’ve rebelled against it a little bit. There was always the thought that your clothes shouldn’t cost too much or they couldn’t be too bold. My grandfather, who was a steelworker for most of his life, would always call people “common,” which was a great compliment for him. But he was the kind of guy who kept his shoes shined and wore a suit to church, so there was also a certain importance to dressing for an occasion. Maybe that’s merely a generational thing rather than a regional thing. Regardless, I try to have a little humility in the way that I dress and I certainly have a great respect for what I consider to be a fairly traditional way of dressing. That being said, I love patchwork tweed and go-to-hell trousers, so maybe I’m contradicting myself.
IS: When did you become interested in clothing?
CW: I first became interested in clothing around age 13 or 14. It was sort of the #menswear heyday online. Everyone had a Tumblr or a blog. I would come home from high school, rushing to read the Pitti Uomo street style roundups. There was also a lot of interesting retail happening then. J. Crew was at its peak, introducing your average shopper to Alden or Barbour. I can remember making a trip to New York to visit Rugby, RRL, and Gant, when those were all a block away from each other on Bleecker Street. Sid Mashburn, of course, was a huge influence at that time. Probably some of the first items I bought that were really me were a pair of Nantucket reds and an old Corbin navy blazer. I think my parents were very confused.
IS: You went to school for fashion in Ohio. This, obviously, had to have been hugely important to your development. Tell us a little bit about your experiences there.
CW: I went to The Fashion School at Kent State University. It was a good four years and I’m happy to have gone to a smaller school in Ohio. Looking back, I realize I wasn’t ready for New York. I’ve never been much of an academic, but I learned a valuable skill set from these experiences.
IS: What brought you to New York? Did you move there to work at Drake’s specifically, or did that opportunity arise once you were already there?
CW: I finished my last exam on Wednesday and was in New York on a Friday. I’m lucky that my brother had a couch to sleep on as I worked an unpaid product development internship for a couple of months. I think everyone in the industry has a similar story. I knew the boys at Drake’s, Alex Winchell and Matt Woodruff, through Instagram and, rather fortuitously, Matt reached out to me as I was wrapping up my internship and asked if I’d be interested in applying for the job at Drake’s.
IS: What did you do there, and how did it influence your outlook on style?
CW: I worked in a few roles during my time at Drake’s, doing some wholesale as well as retail on the shop floor. Those first few seasons that they did RTW were really something special, some of the best look books I’ve ever seen and the product at that time was not only incredible quality, but actually a very good value. I have a dear friend, Glenn, who used to work down at H. Stockton in Atlanta. He once told me, “You guys are the most exciting story in men’s clothing in the last decade.” I still think about that a lot. Our crew was really special and I’m immensely proud of all of them, for what we did then and what we’ve all moved on to now. It was great to be defining a certain look in the city and to be inspiring a lot of young guys who I think would have been intimidated otherwise.
IS: What led you away from Drake’s and to J. Meuser?
CW: Ultimately the tides were changing and the whole crew trickled out the door. At a certain point, I was ready to step into a more exciting role. Luckily, Matt had just started at J. Mueser and Jake Mueser had asked me if would be interested in coming aboard as well. It’s good to be doing something a little more tailoring focused again.
IS: Can you tell us a little bit about J. Meueser as a company? What is their house cut?
CW: Jake started J. Mueser about a decade ago. We have a ready-to-wear shop at 19 Christopher Street and a small space for bespoke fittings across the street. The bread and butter of the brand is definitely our custom clothing, which is a fairly reserved, Neapolitan silhouette, though we also have bench-made make that is done here in the States, and is much more Saville Row in its silhouette – think something akin to Anderson & Shepherd. We’re also starting to expand our ready-to-wear, which includes a really nice line of soft coats that are machine made in Naples, are made up in a shirt construction, and retail for right around $1,000. Value is something that’s important to me, I want to know that what I’m offering to the guy that maybe doesn’t have a closet full of suits is a good deal.
IS: You’ve had a significant hand in the formation of Wythe. How did that come about?
CW: Wythe has been a fun project to consult with. It’s been fun seeing our following increase and seeing the outpouring of support from our Kickstarter. Wythe is amalgam of so many things: it’s a love of New York as a second home, it’s a vintage deep-dive, it’s making something that your average guy can actually afford to buy. We showed the first collection for Autumn/Winter 2020 at MAN a couple of weeks ago and had a really great response.
IS: The first items coming from Wythe were very Ivy: sturdy yet soft OCBDs with a beefy collar role, breast pocket, locker loop, and a relaxed fit. The first full collection, coming later this year entitled “Slow West,” seems to be geared more towards a Western look, described as “a new vision of Americana.” How did this transition come about? Do you see a return to more classically Ivy items in the future?
CW: I wouldn’t necessarily call it a transition as I think that was always the intent. It’s a mixture of a few different facets of American clothing. For example, next fall we have some great Shetland sweaters coming down the pipeline. So we have that and the oxfords juxtaposed with some chamois pearl-snap western shirts and cowboy boots. We’ll continue to have a mix of these sorts of products and looks as we move along.
IS: One thing you drew some criticism on was the decision to use alpha sizing rather than standard neck and sleeve measurements. Can you shed some light on that choice?
CW: We did draw some criticism from the Ivy-Style.com crowd. Oddly, we didn’t actually hear any negative feedback from the folks that donated over $20,000 to have the shirts made. I’m of two minds, and see a value in both. For now with, our budget and the amount of inventory we can handle, they will continue to be alpha-sized. I would ask anyone who is skeptical to give them a try, I really think they’re just about the softest oxfords I’ve ever worn.
IS: You’re also the founder of the Bullshot Book Club which includes many young luminaries of the New York classic menswear scene including Drake’s and J. Meuser colleague, Matt Woodruff; Wythe co-founder, Peter Middleton; Ralph Lauren alum, photographer and designer, FE Castleberry; and a host of other friends and colleagues. Obviously your focus is on only the highest forms of literature (and perhaps some libations make their way into the mix), but does clothing ever come up? You must bounce ideas off one another…
CW: That’s right, I think there’s all but two of us that are in the men’s clothing industry. We don’t make it a point to talk about clothing, but inevitably it will come up. Really, we’re there to chitchat, drink, and hopefully discuss the book. The Bullshot Book Club is more than clothing, it’s a good steak, fries, and a good cocktail. If you can’t enjoy that without telling somebody about your “natural shoulder sportcoat” then you’re not really living. It’s about creating an exciting community that people can follow along with and engage with. But to contradict myself again, I should have a Bullshot Book Club club-tie coming out soon, along with a restock of the classic Bullshot Book Club ball cap.
IS: How has the Ivy League Look specifically had an influence on you?
CW: The Ivy League Look had a huge influence on my personal aesthetic. It’s still largely how I dress, I just probably arrive at it from a different avenue than a lot of people. My tailoring may be Italian but I still wear an oxford-cloth shirt with a button down collar just about every day, usually with a repp tie, and a pair of Aldens. Having such a traditional look allows me to have some fun with certain aspects, like wearing a funky pair of Padmore & Barnes Wallabees, or a bold pair of sunglasses, for example.
IS: You seem to draw heavy influences from a variety of places, including classic American looks like Ivy and preppy, British country wear, and custom Italian tailoring. How do you mix these elements to cohesively form a singular style?
CW: I draw inspiration from a lot of places. My greatest influences are definitely the Sloane Rangers, the BCBG, and the preppy look. Especially as we head into spring, I’m already madras shopping. But I also draw a lot of inspiration from western wear, I wear a wrangler denim shirt or a Lee 101J most days. Everything I like comes from some sort of tradition, be it American or French or whatever it may be. That’s why I think you can throw most of it together without a lot of thought and it will always work.
IS: Finally, something of deep interest to me: social media and menswear. Social media gets many young men into classic menswear that would not have been exposed to it otherwise. How has it influenced your style journey?
CW: Social media is a great tool. I think sometimes it can breed an obsessive nature in us clothing nerds that’s definitely a little bit unhealthy, but it’s a wonderful networking tool and it’s really the reason I’m here to begin with. If it wasn’t for the many menswear blogs, Tumblr, and eventually Instagram, I probably would be on a very different career path. Nowadays, I use mine to show what I’m wearing, what I’m excited about, and, more than anything, to showcase the various personalities in this tight knit scene. If I had to give any advice to young people looking to get into the industry, it would be to embrace Instagram or whatever is coming next, and not only put content out there, but also reach out and interact with people, keep in touch, and maintain those relationships. I’ve found this to be immensely helpful in my professional life.