TK: From the outside, the WM Brown lifestyle looks effortless—beautiful places, incredible food, travel, great clothes. But behind it all is a tremendous amount of work. How do you balance the romance of that life with the reality of making it your career?

MH: I think it's really a gift to make hard work look easy.

I genuinely love what I do, and a big part of that job is the lifestyle it requires—travel, exploration, meeting people, discovering places. But none of it happens without an incredible amount of effort.

When I'm at Pitti for a week and then immediately head to Milan, I'm exhausted. I prepare for those trips. I do my homework. I want to be the best student I can be. Producing the magazine and creating the content requires a tremendous amount of planning, concentration, and energy.

It's not roofing houses or selling cars, but it's still work. It just happens to revolve around the things I love.

TK: One thing that's always stood out is how natural your style feels. What's the difference between someone who simply buys good clothes and someone who has genuine personal style?

MH: Style is personal.

You look at people like David Coggins, Michael Williams, or anyone whose style I admire, and we're all very different. What connects us isn't that we dress alike—it's that we each have a point of view.

My own style comes from growing up as a preppy kid in upstate New York, but over time I've woven Italian tailoring into that foundation. I'm still chasing many of the same ideas I admired when I was younger: American prep, great tailoring, Ralph Lauren, vintage denim.

Film has always been a huge influence too. Robert Redford in The Sting. Dustin Hoffman in The Graduate. Those cinematic references stay with you.

And honestly, my father probably influenced me the most. During the week he'd wear Levi's, a Tattersall shirt, a Barracuta jacket, and desert boots. On weekends he'd put on Harris Tweed. Watching him get dressed taught me that style wasn't about trends—it was about consistency.

TK: You've worn shoes from some of the finest makers in the world, yet you always seem to come back to Alden. What keeps bringing you back?
MH: For me, it starts with comfort.

The first time I put on an unlined Alden Leisure Handsewn in snuff suede, I knew immediately. I could walk fifteen miles in that shoe.

I've made plenty of bad shoe decisions over the years. Everyone has heard the salesman say, "It'll stretch." I've learned not to believe that anymore.

The Alden just fits.

It's beautifully made, the toe shape is fantastic, it captures everything I love about the classic American penny loafer, and it's still handmade in Massachusetts. They've become more sought after over the years, but they've remained incredibly true to their roots.

TK: They're also remarkably versatile.

MH: That's exactly why I keep wearing them.

They work with shorts. They work with tailoring. They're perfect on an airplane because you can slip them on and off.

I've tried plenty of other loafers over the years, but I always come back to Alden. I think I own four pairs in different stages of wear. Some I've had rebuilt by Alden, and sometimes rebuilding them just gives me an excuse to buy another pair.

They're the kind of shoe that only gets better the more you wear them.

TK: The Alden x WM Brown x Tailors' Keep collaboration doesn't reinvent the shoe—it simply celebrates one that's already become a favorite. Why did that approach feel right?

MH: Because there wasn't much to improve.

It's already one of the best loafers ever made. The collaboration was really about celebrating something we all genuinely wear and believe in.

Getting it made wasn't easy. Alden is incredibly traditional, almost frustratingly so at times, but that's also why the shoes remain so special. They're committed to doing things the way they've always done them.

I respect that.

TK: The new Summer Issue of WM Brown also launches on the West Coast during the event. What can readers expect?

MH: This issue features my friend Alessandro Peroni on the cover.

We photographed him throughout Athens wearing his own collection, which is built around warm-weather dressing—beautiful linen trousers, overshirts, and incredibly versatile pieces.

One thing we've always tried to do at WM Brown is feature real men with genuine personal style. We're not interested in dressing models. We're interested in documenting people whose style naturally inspires us.

We also have an incredible surfboard archive photographed by Dewey Nicks, a story on the history of the Barracuta jacket—which has a personal connection because my father wore one for years—the launch of my new Timex collaboration, and one of my favorite stories we've published: Yolanda and I driving our Fiat Panda from Lake Garda to Bordeaux.

It's a very summer issue in every sense of the word.

TK: You're returning to San Francisco for the launch on July 16. What keeps bringing you back?

MH: I've always enjoyed coming back.

Tailors' Keep has built something really special. They're pushing classic menswear forward in a city that's often known more for hoodies than tailoring.

It's exciting to see that kind of style culture continue to grow, and I'm looking forward to celebrating the magazine and the shoes with everyone.