A Few Questions with - Miles Fisher

Actor, entrepreneur, and eternal optimist Miles Fisher on mastery, clothes, music, and why people remember how you made them feel far longer than what you wore.

I've met only a few others who are as focused as Miles Fisher.

Miles gets an idea and runs with it. He’s constantly looking for ways to challenge himself, improve, and ultimately connect with others. I’ve been known to gas people up here and there, but I get a lot of it from Miles. Every phone call, text, or even LETTER, he reminds me (and I’m sure countless others) that life is a gift.

He’s an entrepreneur, an actor, a musician, an athlete, and don’t get me started on his watch collection…It was only fitting that he took an afternoon to answer a few questions.

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What’s a song you can’t stop listening to right now?

“Ithaca” by Beatenberg.

What was the first album you bought with your own money?

Counting Crows, August and Everything After. I still know every word.

If you could only keep one record in your collection, what would it be?

Paul Simon’s Graceland. It’s never wrong.

Is there a concert or show that changed the way you see music?

A Lessons and Carols service when I was a young boy. I remember “Once in Royal David’s City” being sung - the soloist chosen last minute, candlelight, a procession moving slowly through the nave. The Anglican choral tradition is genuinely majestic. That was the first time music felt like something more than sound.

What’s the oldest piece of clothing you still wear?

A rugby shirt I bought on a road trip through New Zealand with my siblings. That was twenty-five years ago. Thing still holds up.

Do you remember your first big fashion splurge?

A bespoke jacket from Huntsman. Dario Carnera cut it. Porter & Harding Glorious 12th cloth— green check wool, 340gsm. It was an absurd thing to do at the time. It is among the best pieces I own.

What’s an item in your wardrobe you’ll never part with?

My college club ties. They’re not going anywhere.

Who do you look to for style inspiration?

A few Spanish and German aristocrats. I’ll leave it at that.

Do you have a uniform or go-to outfit?

Suede loafers, no socks. I’ve worked through most of the canon - Alden, Lobb, Ed Green, Baudoin & Lange, bespoke and a smattering small brands from Spain and Argentina you’ve never heard of. Best fit and wear for my foot is the Crockett & Jones Harvard 2 on a rubber sole. That took an embarrassingly long time to figure out.

What’s the best advice you’ve ever received about your work or craft?

Master something. Mastery is the best goal because the rich can’t buy it, the impatient can’t rush it, the privileged can’t inherit it, and nobody can steal it.

What’s a book that has stayed with you?

The Death of Ivan Ilyich. Tolstoy in forty pages does what most novelists can’t do in four hundred.

Do you have a daily ritual or routine that grounds you?

I try to write by hand for at least thirty minutes before the sun comes up. It’s a good way to metabolize whatever the unconscious has been working on overnight. Communication and articulation is difficult, even to oneself. Practice it.

What’s one object in your home that tells a story?

The day I graduated from college, I left as tour manager for the Harvard Krokodiloes on a 25-country, six-continent trip around the world. This was before e-tickets. I saved every flight stub from that journey and had them framed. You can trace the whole arc of it — a trip that spans the globe. The ink has faded. The memory hasn’t.

What’s something you believed about style when you were younger that you don’t anymore?

I used to think a man’s wardrobe should mirror his life, that intentionality meant dressing for the reality you actually live in. Meetings call for one thing, a casual life refines that. I thought style was about alignment. I’m less convinced now. The more interesting dressers I know don’t dress for their circumstances. They seem to be dressing for something internal that I’m still trying to name.

Who was the first person you saw and thought, “That’s what cool looks like?”

In the early 2000s, I fell down a rabbit hole of contemporary Chinese cinema. Watching early Wong Kar-wai, I became enamored with a young Tony Leung. Somewhere in the middle of In the Mood for Love , I remember actually saying it out loud - that is what cool looks like.

What’s a brand or designer you think people will be talking about in 10 years?

Hermès... if the Dumas family can keep it under sole ownership.

What’s something you’ve always wanted to learn but haven’t yet?

Bridge. Many of the most intelligent people I know hold that game in higher reverence than anything else. It strikes me as intellectually very elegant. Though at my age, truly committing to it might be a bit indulgent.

If you could pass one piece of advice about style to your younger self, what would it be?

People will forget what you wore, but they will not forget how you made them feel. A truly well-dressed man isn’t just elegant in appearance; he’s generous in spirit. That’s the whole thing, really.

What Substacks do you follow?

I’ll be honest, it’s a lot of women who are putting out incredible stuff. Of course, it’s Emily Sundberg’s world and we’re all just living in it, but the commanders of the Pacific and Atlantic fleet - Rachel Karten and Ochuko Akpovbovbo - always cue me into something fascinating before I’d find it myself. The OG’s, Yolanda Edwards and Lizzie Mettler, always deliver. I got into the art of the form through Celine Nguyen - her essays are so good I never realized an email newsletter was capable of that kind of nuance. Also looking forward to what Rickie De Sole does now that she’s at Airmail.

Your Substack, Fisher’s Island, what’s it all about?

I was an English major in college and wanted to go back to the creative gym. I wanted a place to write about what it actually takes to author your own life instead of letting algorithms, careers, or other people’s expectations write it for you. So that’s what it’s become — essays on fatherhood, sobriety, ambition, taste, and institutions that shape us whether we like it or not. It’s not advice, just me trying to get a little closer to the truth in public, in real time.

Thanks, Miles 🫵😎