Acceptance of self is a stage of life that everyone should pass through, but not everyone does. Some of the most “wildly successful” people I know have absolutely no clue who they are, no understanding of what they believe, and no notion of how to express themselves, and I sympathize with them because I know how long it took me to feel comfortable to be the man I am.

I grew up in a beautiful-but-smallminded suburb of Chicago, where the ignorant, corn-fed sheep adhered to the adage, “The nail that sticks out gets hammered.” In my early teens I showed up to school in a pair of checkerboard Vans slip-ons, and the boys who spent their summer together at football camp made fun of me and my “gay” shoes.

After school I went home and cried and decided it wasn’t worth being different if it meant being judged, so I abandoned my style and assimilated with the rest of Midwestern America, because maybe if I wore what those guys wore, they would want to be friends with me. And wouldn’t you believe it, they became my friends once I started wearing oversized JCNO jeans, stark-white K-Swiss shoes, backwards trucker hats, too-tight Abercrombie tees, and many other horrors I have to relive when I thumb through our family photo albums.

For years I emulated the wrong people so I could hide in plain sight and feel accepted, when really I was alone and misunderstood. I let fear of being different dictate who I was and what I shared with the world, but now I am comfortable enough to express myself however comes most naturally.

A lot of days I don’t care what clothes I’m in—because what I wear matters far less than what I do or what I say—but occasionally I like to get dolled up so I can feel distinct and confident when I walk out the door. I want to spend as little time as possible thinking about what to wear—because before long the vanity of it all starts to stress me out—so over the past few years I have been thinning out my closet to keep only the unique, timeless items that complement well and best accentuate who I am, really.

A local friend Mr. George collects vintage hats and sells them out of his home studio, and about a year ago I picked up this Stetson “pork pie” from him. While I would most definitely wear it every day, I prefer to keep it for special occasions, like work events or date nights. Not long after I started wearing this hat a few of my friends asked for introductions to Mr. George to buy dead-stock Stetsons of their own. 

These made-to-order boots take three to four weeks to produce at Rancourt, a family-owned footwear manufacturer in Maine. When I was editing Iron & Air Magazine we collaborated with Rancourt to launch this boot, the Traveler, in two colors—black and brown—but my Travelers are a bespoke pair that use Parisian Blue leather from Horween. They are by far the best boots I have.

Last Christmas my family traveled to the Hawai’ian island of Kauai, and at a small, funky vintage shop in the town of Hanalei my girlfriend found this zzzzzzzz button-up. Even before I tried it on I knew I was buying it—because when your girlfriend says something is “cute,” you buy it—and I’m very glad I did, because it is the least garish Hawai’ian shirt I’ve ever seen, and I can easily wear it to a backyard luau or a party in the Hollywood hills. 

The &SONS Sunday shirt is worn every day, because it is the softest, most versatile shirt I own. Cotton-twill construction means the shirt is tough and feels substantial, but with eight-percent stretch it never feels stiff or restrictive. After a week of living in the shirt, I said to &SONS founder Phil James, “With any luck I’ll still be wearing this shirt when I’m 65 years old.”  

My brother introduced me to Tokyo-based fashion designer Jonathan Lukacek, who works for some of Japan’s most respected brands and has a website called The Bandanna Almanac, where he documents his charming love for historical bandannas. For a while Lukacek had a side project called “Made by Grandma for Mafia,” and used quilt blankets to make bomber jackets, and when I wear my quilt bomber I get as many odd looks as I do gushing compliments.

Every year I look forward to the Handbuilt Motorcycle Show in Austin, Texas, because Austin is one of the most fun cities in America, and the shop that hosts the show, Revival Cycles, is home to some of the best people in the motorcycle industry. It’s been six years since I bought this tee at the inaugural Handbuilt show, and I cannot wait to go to this year’s show in November; typically, the show is in April to align with Moto GP weekend at Circuit of the Americas, but due to COVID-19 Moto GP weekend moved to November, so Handbuilt did, too.

The kids in The Sandlot wore PF Flyers, so as a boy that’s what I wanted, but instead my mom got me high-top Converse Chuck Taylor All-Stars, and I’m happy she did. The Chuck is an inexpensive, all-around casual shoe that never goes out of style and looks better with every blemish and scuff. My favourite modern version of the shoe is the Chuck 70, which uses a wing tongue-stitched canvas body and a thicker, softer insole. 

These glasses belonged to my best friend and dad, Steve Nelson, who five years ago died from cancer. I kept only a few of his things—neither of us were ever particularly sentimental—but I made sure to hold on to these, thinking that when my vision faded I would repurpose the frames for myself. When I turned 30 I suddenly had astigmatism, so I dug out the frames and had them fitted with lenses, and now when I sit down at my computer, I feel a little bit closer to the person I miss most.