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Daily Inspiration: Meet Justin Holiwell

Today we’d like to introduce you to Justin Holiwell.

Hi Justin, we’d love for you to start by introducing yourself.
I’ve always been interested in how I present myself, going back to wearing my first tux as ringbearer.
My wife has a running joke that I’ve had more fashion eras than Taylor Swift’s tour. She’s not wrong. 2000s preppy, skater phase, coastal casual, the capsule wardrobe obsession, streetwear, full sneakerhead mode. I’ve been in all of them. And at some point, you realize you’ve been treating your wardrobe like a costume department, always looking outward for whatever the current reference is.
The shift happened gradually. It started feeling less like something I was performing and more like something I was building. I stopped asking “what’s the right thing to wear right now” and started asking “what actually fits the way I see myself.” That’s a different question.
My clinical background plays into this more than people expect. In practice, you’re trained to sit with a patient, take a history, and understand what came before to understand what’s happening now. I started approaching garments the same way. What informed this piece? What problem was it solving? Who was wearing it and why? That’s not just a nerd spiral. It actually changes how you relate to what you own.
And then my dad’s closet happened. Tweed blazers. Rep ties. A pair of fisherman sandals with years of backyard cookouts and vacation fits built into the leather. The kind of patina you cannot buy. That was the moment I realized I wasn’t just interested in clothes. I was interested in what things carry. The history, the inheritance, the cultural lineage underneath the aesthetic.
That’s what the work is really about now.

We all face challenges, but looking back would you describe it as a relatively smooth road?
Honestly? No. Two different kinds of hard.

The first one is internal and it never fully goes away. Learning the difference between dressing for yourself and dressing for validation sounds simple until you’re actually standing in front of a mirror trying to answer it honestly. Even now, I’ll pick something up and have to sit with it for a second. Do I actually want this, or do I think it’ll perform well? Those aren’t the same motivation and they don’t produce the same result. The clothes you buy for validation tend to sit in the back of the closet. The ones you buy for yourself are the ones you reach for without thinking.

The second one is more practical. Being a creative in spaces that don’t take creativity seriously. I heard “that’s a nice hobby” more times than I can count. And the implication was always clear: real life is over here, that thing you love is over there, and the two don’t touch.

Then there’s the version of that struggle that’s entirely self-imposed. Deciding which creative outlet gets the front seat. Do I double down on the podcast? The DJ sets? Content? They all pull. And none of them feel like the wrong answer, which somehow makes it harder to choose.

What I’ve landed on is regular check-ins. Is this still serving me? Not “is this performing,” not “is this what people expect from me.” Is this still the thing I actually want to be doing right now. When the answer is yes, you keep going. When it’s not, you adjust.

That’s still the practice.

Thanks for sharing that. So, maybe next you can tell us a bit more about your work?
I think of myself as a creative and a community builder before anything else. Those are the two things that run through everything I do.

On the fashion side, the content I make is less about “here’s what to wear” and more about why certain things exist in the first place. Brands, trends, specific garments. They all have a lineage. Most people skip that part. I think the context is the interesting part. Understanding where something came from changes how you relate to it, whether you’re buying it or just wearing it.

The community piece shows up most clearly in the music work. I’ve been DJing for years, but at some point I started thinking less about individual sets and more about what kind of spaces I actually wanted to exist for people like me. That led to building a collective of DJs and eventually launching Interlude, a DJ and coffee morning event. Low barrier, communal, the kind of thing you don’t see a lot of in the spaces I move through. Building that from scratch is probably what I’m most proud of. Creating something that didn’t exist because I wanted to see it.

What sets me apart is probably the thing most people don’t know about me. I do all of this while working a full-time job as a physician assistant. Clinical practice, daily. And the two worlds inform each other more than people would expect. The way I approach a patient, building a history, looking for what’s underneath the surface, is the same way I approach a garment or a brand or a cultural moment. I’m not opining. I’m diagnosing.

It’s a different access point. And I think it shows in the work.

Do you have recommendations for books, apps, blogs, etc?
A few that I keep coming back to across different parts of my life.

For fashion specifically, Articles of Interest and Blamo are both essential listening. Die Workwear too. These aren’t casual podcasts, they actually do the work of tracing things back to their origin. Which is the kind of content I respect and honestly try to make myself. On the reading side, Amitora and Black Ivy are probably the two I’d hand to anyone serious about understanding menswear at a deeper level. Not just what looks good, but why it looks the way it does and who built it. The Bengal Stripe, Sprezza, Jake Wolf, Where the Pants Break on the blog side. All worth your time.

For books that have nothing to do with fashion but shaped how I move: The Subtle Art of Not Giving a F*ck and You Are a Badass both hit at the right time in my life. Dark Matter is one I think about more than I expected to. And This Is Not a T-Shirt from Bobby Hundreds is genuinely one of the best things written about building something creative in a culture that doesn’t always take you seriously.

Practically speaking, Depop is where I spend too much time and I make no apologies for it. Pinterest too. Outside of the ad situation getting out of hand lately, there is still so much untapped inspiration living there. If you know how to search, you find things the algorithm hasn’t touched yet. Notion keeps me functional. I wear a lot of different hats and without a system I’d drop all of them. And YouTube is still underrated as a research tool. I’ve gone down more rabbit holes there than anywhere else.

On the creative production side, Mailnote has become essential for building pitch decks. Honestly, I might enjoy making the decks more than making the actual content. There’s something satisfying about having the vision clean and organized before production even starts. And Premiere Pro is just non-negotiable. Best editing software in the game. The tool that makes everything else presentable.

The Ladder app for workouts. That one’s just part of the routine at this point.

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Person shopping for coats in a clothing store, browsing gray and red jackets on racks, wooden floor visible.

Man wearing sunglasses and a light blue shirt DJing outdoors with greenery in background.

Man wearing sunglasses, a cap, beige jacket, and jeans, sitting outdoors holding a drink, with trees and a vehicle in background.

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