Chase Winfrey
Where did you grow up?
Middle of Ohio, close to Columbus.
Do you think growing up in a small town had an effect on your style or how you felt about style?
Yeah, maybe a little bit. I think my aesthetic is very traditional American. I think there is probably not as much international influence in the way I dress, which I think if I grew up in New York or Los Angeles, that would not be the case.
I know you had a Tumblr phase, was that your introduction to menswear?
Yeah, I guess to that point, growing up in Ohio meant a lot of my exposure in terms of men’s clothing came from the internet. As I’m sure is true of anybody my age. Even more so, being in someplace that would be a little bit of a desert in terms of clothing. So yeah, Tumblr that sort of phase and that phase where everyone had a menswear blog.
I feel like you were introduced to menswear at the height of menswear blogs.
Oh yeah, definitely. Also, while that was happening was I think, for me, the years where you’re deciding what you want to do with your life when you’re 14/15. When you’re really thinking about what you want to do, it was definitely an influential time.
What blogs would you read?
Secret Forts, which is great, and I still go back to all the time. A Continuous Lean. WM Brown, obviously. I was a big fan of Unabashedly Prep; I loved Freddie's [Fred Castleberry] blog. His street style is great. I’m trying to think of what else. Those were probably the big ones.
Is it exciting working with those people now?
It is, it was really weird when I moved to New York and started working with Freddie. I was a very big fan of his blog and definitely had images saved that I think about, just because it was the perfect execution of whatever weird prep thing. His aesthetic has evolved so much since then; back then, it was much more of his street style, which was really interesting.
Especially for your exposure, not being in New York getting to see his take on street style.
Definitely! It’s very cool, that’s the beauty of New York.
Do you remember the first thing you found that gave you that feeling of “this is it!”?
Nantucket Reds. I was probably like 15 or 16. I don’t know where I had seen them. I remember being like, “Where can I even get these?” A town of like 2,500 people in Ohio, “Where do I even buy these pants?” I remember being like, “Oh, I can just order these from Ralph Lauren. This seems cool!”
The internet exists!
I’m very colorful naturally, and there is something so great about the Go-To Hell thing, as obnoxious, and overused as it is, I want a loud jacket. I want pants with whatever embroidery on it - I can’t help it.
Before you got the pants, what was the outfit?
I think I always liked to dress up, but it just wasn’t in a way that was cohesive and tied into a specific style of culture that I understand. I was probably 14 or 15 when I said, “Preppy is cool. I like that!”
Did you wear the pants to school?
Oh absolutely! I wore them everywhere. I immediately was like, “I need a navy blazer.” I just always had liked kelly green chinos and a navy blazer. I looked like everyone’s least favorite fraternity brother, but I was like 15, and my mom would always be like, "We are just going to the grocery store. You don’t have to have this on.” I was like, "Well, but I want to wear it.” My dad was always like, “Leave him alone! He can wear whatever he wants!” My mom was like, “I just don’t want to be seen with him out in public!”
That’s super funny! How do you think your style has evolved from those days?
It’s definitely gotten a lot less “brash.” That being said, I would still love another pair of kelly green chinos. Maybe this summer? But, yeah, it’s definitely toned down a lot. Lots of different influences there too. It’s definitely matured. I don’t necessarily think I still look like a fraternity brother. I think I try and use vintage in a smart way. I don’t ever want to have a vintage look, but I like to use vintage pieces a lot.
So, you don’t want to go full ‘30s? What’s your time period? Or ideal birth year?
No, I never want to go full ’30s. Late ’50s, early ’60s. I like the way the Ivy League campuses looked and the way the ’50s before the Ivy heyday. I also love anything ’80s. To me, if you’re talking about prep, it’s like Beamers and Nantucket Reds and the most obnoxious stuff you can imagine.
I like that the Nantucket Reds were the piece that changed it. Would you go back and buy them again? Do you still have them?
Absolutely. I definitely have them, the problem is that they were very short which was also a point of contention with anyone in my life. I was always like, “Well, the pants have to be above the ankle!”
No socks? Classic Sid Mashburn move.
I’m obviously not going to wear socks because that’s wild! If I had not been 16 and had been able to afford a pair of double monks, I totally would have bought them.
What was the go-to shoe?
Penny loafers - just Weejuns. I always wanted the classic Alden tassel, which was like the perfect shoe. I worked at a little store when I was in Ohio, and we would just drool over that shoe; it was like $800, which, when you’re basically unemployed, seems like a million dollars.
When you did eventually get that pair what was that experience like?
When I moved to New York, and I worked at Drake’s, I ordered a pair through them. It was an emotional experience. I still remember the exact night we got them. We were having a party at Drake’s, and we were opening the box and putting them on. The thing about the Alden tassel is that they always come with a blue rubber band around the tassel. I was standing there looking at them with that blue rubber band on them, and I felt like I could cry. It was just what I’ve always wanted. I still love them. They’re my absolute favorite shoes. The best shoe a man can own easily.
Do you have an emotional connection to clothes?
Oh easily. Very very much so. My Barbour, that thing is like my best friend. It’s been through every bad night. I’ve slept in that thing.
When did you get it?
I got it on eBay my freshman year of college. So it’s a little bit old now. It’s starting to get some patches. The best coat ever!
Do you remember the first time you met one of those influential menswear guys?
It’s always really exciting to meet people you’ve read about online. It’s like, you know how it is in New York you run into actual celebrities, but you kind of have to act like they’re not a celebrity, you’re like “Oh hey… man!” Or maybe you’re like, “Love your work.” Maybe.
If anything. Only if there’s an awkward silence!
“Oh by the way - ”
“Oh, by the way - I’ve seen you in something. Let’s not pretend I haven’t.”
But yeah, it was really cool to meet David Coggins for the first time. I’ve read everything he’s ever written. Bruce Boyer was a big one. He’s the nicest guy I’ve ever met. The weirdest thing too, Bruce, when I first met him, immediately called me by my Tumblr handle.
Are you going to give that out? Should I link it?
It’s called The PopinJay. It’s like a mockingbird … anyway, as soon as I saw him, he was like, “Your tumblr, you don’t post that much anymore.” I was like, “No one does, but I’m glad you follow along with it.” Now that’s what he calls me. Matt Hranek was so cool to meet. As I said, I’d always read his original blog, and the first time I ever met him, he came up to Drake’s. He’s the only person I want to see smoking a cigar - that’s the thing about Matt. I remember Matt came up to the door he’s got whatever Barbour on, his big aviators, and he’s got a big cigar. He walks up to the door, and I’m like, “WHO is this guy?!” He does a salute, takes his cigar and leaves it on the stoop, comes in, and is like, “Hey boys! What’s going on?!” We were all like, “This man has a lot of energy!” He wanders back out, picks up his cigar, and goes on his way. He’s so cool.
Matt’s great! It’s cool too because you’re at the age where you got to grow up reading what those guys wrote, but you also get to work with them.
It’s important to be a little bit of a fanboy, I guess.
I think you appreciate it a bit more too.
There’s nothing worse than somebody being too cool for school. I’m doing what I’m doing because I’m passionate about it, and I find the community really exciting.
You followed them for so long that it’s obvious you had a love for it for a very long time. You were 14 and wearing Nantucket Reds and a blazer to school; there is proof that you’ve liked it for a long time.
I’ve pretty much always looked like this!
Is there anything you buy “too much” of? Or what other people would consider “too much”?
Neckties. I buy a lot of neckties. I love them! I wanted to be a neckwear designer for a long time.
You still have time!
I wear a tie basically every single day, and I have for a decade. I have a lot … probably a little over 1000.
Oh. Yeah, some would say that’s too many.
Some people would say that!
I think that’s the most significant number for the question I’ve gotten by … a lot. I guess they don’t take up that much space, compared to other things.
Well, 1000 takes up a lot. But I tell myself they don’t take up that much room.
It’s not like … mine is shoes which kind of occupy a great deal of space
Shoes take up a lot of room. Neckties, it’s like a handbag for women. It’s not about practicality, it’s just a beautiful object. Everything else about men’s clothing, for the most part, is based around utility. A necktie is just fun! It’s colorful.
Do you revolve your outfit around the tie? Do you pick that first? What’s your process? Do you just wake up in the morning and decide then?
Less and less. I probably used to. Probably the sport coat. I like a big pattern. I’d probably go with a sport coat first and decide from there, but I don’t know! I’m not one to plan out my outfits. I do change very often in the middle of the day.
What is your average number of outfits per day?
Probably two. If I’m at work I’m probably going to change.
Mid-day? Afternoon?
So, Mat [Woodruff] and I have always had a “mid-day tie change.” So there is always that point in the day where we are like, “I’m feeling like a mid-day tie change.”
I laugh, but I also change sometimes too.
Usually, two outfits. I don’t think that’s too wild.
Yeah, one for the day, maybe one at night.
Maybe three who knows.
I think once you pass three -
Things are getting a little wild.
Out of hand.
I think when I was in college, I wanted to think about what I’d wear, and then I would sit stuff out, and I’d never end up wearing it. By the time I’d wake up in the morning, I didn’t want to wear it anymore.
So you have a book club, Bullshot Book Club. Tell me a bit more about that!
I do. Basically, my friend Steph and I, we were having dinner at JG Melon, the original. I had never been there before. He said, “If you come to JG, you have to have the Bullshot.” I was like, “What is this?” Basically, it’s like a bloody mary but without the tomato juice subbed in as beef broth. Which sounds disgusting I will be the first one to admit, that sounds really gross. So we ordered those. Meanwhile, we were having this conversation about reading a couple of books. He’s a really big reader; I’m a really big reader, so we were talking about reading a couple of books together. The first of which was Infinite Jest - maybe we finished it, maybe we didn’t, it’s not important to get into at this juncture. So, we were talking about reading it at the same time. He said we should have a little book club. I said, “Why don’t we invite all our friends?” We have a pretty tight-knit group of guys, so we decided to invite everybody. We were like… “What should we name it?” We were sitting there drinking those bullshots, and I’m like, “It’s the Bullshot Book Club!” That’s basically it.
The origin story!
It’s basically just incorporating a very very weird archaic drink which has a kind of interesting, Manhattan specific history. It’s what Marilyn Monroe would drink, what Hollywood stars would drink when they wouldn’t eat food. It was what the ad men in the ‘50s would drink on Madison Ave. As New York kind of changed and this weird steakhouse culture disappeared in a lot of ways, the drink disappeared as well. There are still these remnants of it. JG, P.J. Clark’s, Donohue’s, or the Odeon. These really classic spots. I’m also just somebody that loves that sort of diner/burger joint. That culture, I think, is really interesting. It’s so specifically New York, too, which is something that I love.
Do you have a favorite book?
I do, it’s not super exciting, I should pick a more exciting favorite book to have. I love any Salinger book. Specifically, I really like Nine Stories. Franny and Zoey is great.
Do you re-read them?
Very often. Franny and Zoey is great; it feels like The Royal Tenenbaums set in the 1950s. It’s that feeling, such a fun book, even if it’s kind of dark. That whole world is so interesting - the Glass family. It’s just fascinating.
Padmore and Barnes?
I am a big Padmore and Barnes guy. I love those shoes. They’re so comfortable. They’re fine dressed down, but they’re so good with a suit. And then there are these guys [points at shoes] which I think are like the OG Country Runner. They’re super light. They have this cool whatever on the back. Cool with jeans and a sport coat.
Can you tell me a bit more about your watch?
So my grandfather got this the year he married my grandmother. But when he passed away, it was just one of those watches that was in a drawer gathering dust. It had broken, and he’d never gotten it fixed; I guess he’d kind of forgotten about it. I wear it every single day. My grandfather was not somebody that had a lot of nice things, and this is just a beautiful object. It works better than any other watch I’ve had.
Aside from clothes, is there something else you nerd out about?
I’m a stickler for a lot of things. I draw, and I paint. Those are definitely things I nerd out about. I’m kind of a stationery nerd in general. Anything around that I’m very picky about.
What are 5 songs you always play?
Daniel and The Sacred Harp - The Band
That’s Us/Wild Combination- Arthur Russell
Can’t Hardly Wait - The Replacements