Drew Joiner’s Journey Through Modern Menswear
Drew Joiner on Menswear, Sustainability, and Creative Growth
"Fashion isn’t just about trends; it’s about storytelling and the confidence to express who you are."
From the very start of Easy On The Ivy, I knew I wanted to incorporate interviews from time to time, and right at the top of my list was Drew Joiner.
For those of us who appreciate Ivy style, it’s easy to get lost in the past. But I believe it's just as important to embrace the future, while carrying forward the best elements of what’s come before.
Based in New York City, Drew is a content creator whose impressive portfolio includes everything from engaging content and podcasting to modelling and beyond.
My introduction to Drew’s work came through the brilliant episode of his podcast, Beyond The Garment, where he interviewed Jason Jules, co-author of Black Ivy.
Listening to Drew’s enthusiasm for menswear sparked my curiosity, and having a blog provided the perfect opportunity to learn more about him!
Tom Hoy: It's a real pleasure to be chatting with you. Your work has inspired many people, myself included, not only in challenging the way we dress but also in being comfortable with how we do so. Was your passion for clothing a conscious decision, or something that happened by accident?
Drew Joiner: I would say it’s somewhere in between—an accident that later became a conscious decision. In the beginning, it was accidental. I was just naturally drawn to fashion, but without much intentionality. I was fascinated by simple things, like sneakers, how they were laced, and even how socks should be worn. These small details caught my attention when I was a teenager, particularly in high school.
It wasn’t something I was fully aware of at the time. But as I got older, I became more conscious of these choices and began to care more about them. I started making deliberate decisions about clothing, style, and aesthetics. Now, it’s something I’m passionate about and think deeply about, but it definitely started unintentionally and evolved into something more mindful.
TH: How would you describe your style?
DJ: Oh, wow. That’s always a tough one to answer. I’d say my style is a mix of many things—it's a reflection of my personal interests, where I grew up, and the aesthetics I care about. Growing up in Colorado, my style was influenced by Western wear, outdoor gear, and technical apparel. I’ve always loved practical clothing, like jackets with zippers and hoods that keep you warm. It made sense with the weather and lifestyle in Colorado. But I also grew up playing basketball, so sportswear and basketball culture played a big role, too—sneakers, jerseys, that whole aesthetic.
As I’ve gotten older, I’ve developed more of an interest in menswear. I’m drawn to Japanese Americana, Japanese denim, Ivy styles, and other elements of that world. My style has become a mix of these influences. At its core, I aim for something timeless and sustainable. I think fashion, like any industry that produces so much, should have a consciousness of sustainability. So, I’d say my style is a combination of timelessness, practicality, and a reflection of contemporary trends, with an eye toward sustainability.
TH: It may feel like a silly question, but I’m interested to hear your thoughts—what were some of the things that drew you to move to New York City?
DJ: There are so many reasons I was drawn to New York. The first thing is the energy. Every time I visited, I felt this incredible buzz—whether it was the people, the events, the creativity, or even just the aura of the city. Growing up, I was a big Spider-Man fan, so that probably played into it, too! But on a more practical level, I love walkable cities. Some of my best memories from college were when I could get around without a car. There’s a sense of freedom in that, and New York is perfect for it.
Then, of course, there’s the fashion scene. New York is the fashion capital of the U.S., and I wanted to immerse myself in that world. Being here has allowed me to learn, engage with the biggest creatives, and be part of conversations I wouldn’t have had access to elsewhere.
TH: Has the city changed or influenced the way you dress? And do you notice your style evolving at the moment?
DJ: Definitely. Before moving to New York, my style was heavily influenced by Colorado—practical, outdoor-oriented, and with a touch of New York flair. But after moving here, I’ve really leaned into menswear. I feel more confident experimenting with things like ties, fatigue pants, and different types of jackets. There’s a boldness in New York that encourages you to go for it, and I’ve embraced that.
As for evolving—yes, my style is always evolving. I think that as a person, I’m constantly changing, and my style reflects that. Sometimes I’m super into fashion, and other times, I step back a little. It depends on what excites me. Right now, I’m really enjoying where my style is, and I feel like it’s maturing along with me.
TH: What are some of the places visitors interested in menswear should check out?
DJ: There are a ton of great spots! First, outside of New York, Canoe Club in Boulder is doing some cool things with menswear, and so is Standard & Strange. But here in New York, definitely check out The Armory—it’s a fantastic store. You can’t leave out Ralph Lauren, either, which has been a guiding force for American menswear for decades.
Some other favourites are Blue in Green, Self Edge, and CHCM. And then there are more niche brands like Atelier Baema T Boa in France—they do amazing shirting. I also love Orslow, which does excellent work in the menswear space, and Taiga Takahashi, which is another really cool brand to keep an eye on.
Taiga Takahashi | LOT.303 COVERALL JACKET
TH: Your recent trip to Japan looked incredible. What were some of your menswear observations while you were there?
DJ: Japan was amazing. What stood out to me was how much attention to detail people there have for menswear. There’s a respect for traditional styles, especially from the 1950s to the 1970s. Even though you see contemporary fashion there, traditional menswear feels much more prominent compared to New York. The silhouettes are different, too—slightly more oversized and with a unique Japanese twist on tailoring. There’s also a strong influence of Americana, but it’s blended with Japanese textile history in a way that feels distinct.
TH: The idea of Ametora and Japan’s interpretation of classic American style has always fascinated me. As someone from the U.S., how do you perceive the Japanese influence on Western style, and vice versa?
DJ: Japan and the U.S. have a fascinating cultural relationship when it comes to fashion. There’s a mutual respect, especially for vintage and reproduction pieces.
In the U.S., there’s this idea that Japanese clothing, particularly in denim and workwear, is of higher quality and more detail-oriented. Meanwhile, in Japan, there’s a deep appreciation for American garments from the 20th century, like vintage Levi’s.
They take these classic items and reimagine them, making them their own. Japan has really kept that heritage of manufacturing alive, and it’s something the U.S. looks to as a model now, especially as we’ve outsourced much of our production.
TH: Where would you like to travel to next?
DJ: Copenhagen is at the top of my list! I’ve heard great things—especially about the city’s biking culture, which I love. I’m curious to see how it stacks up as a hub for menswear. Other places I’d love to visit are Berlin and Italy, especially for Pitti Uomo. There’s just so much I want to explore!
TH: What are some of your favourite items in your wardrobe at the moment?
DJ: Right now, I’m loving my denim collection. I’ve got a pair of Yohji Yamamoto five-pocket jeans that I’ve been living in for the past two years, along with my Sugar Cane Okinawas. I also have some unique button-downs from Ralph Lauren, which I wear a lot.
One standout piece is my Orslow herringbone tweed jacket. It has that perfect professor vibe. I also have a French chore jacket from Orslow that I adore—it’s a blue one, and the founder, Ichiro, even did his own paint splatter on it when I visited Boulder. For footwear, I love my Moorhouse loafers and recently picked up a pair of Allen Edmonds Dallas Roper boots, which bring that Colorado Western touch to my style here in New York.
TH: I think you’re someone who pushes fashion forward. You're influenced by the past but embrace the future too. What are some of the brands people should check out in 2024 and 2025?
DJ: Story MFG is definitely a brand to watch—they blend traditional craftsmanship with futuristic designs in a way that’s really cool. I also love Samuel Zelig for their heavyweight sweaters and hoodies. Another standout is Merz b. Schwanen, known for their loopwheel shirts. They’re doing great things in the traditional manufacturing space.
A more low-key brand I’m really into is Slow Boat New York—they make fantastic contemporary reproductions of heritage menswear. And I have to mention Taiga Takahashi again; they’re doing really interesting work as well.
A huge thank you to Drew for taking the time to chat with me—I'm a big fan of all his work. To explore more of his content, you can find him on Instagram and YouTube.
ICYMI
I’m hoping to grow my YouTube channel, and this is the first of, hopefully, many videos to come.
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Thanks as always,
Tom
Big fan of Drew as well, great interview!