From Baby Booties to Red Ball Jets to Samuel Hubbards: My Life in Shoes

I’m one of 9 children, the second son of a growing brood, and that meant a lot of hand-me-downs.  Lucky for me, my older brother Mike was a rough and tumble kid – an athletic boy who splashed his way to school in puddles, played pick up hoop games in neighborhood parks since he learned how to cross the street, and never met a soda can on a sidewalk that he didn’t want to kick all the way home. What did that mean to me? While I inherited his sweatshirts, jeans, t-shirts and more, his shoes were always too beat up to pass down to me. Talk about the luck of the Irish!

Canvas, unisex Keds? Check. Winking at the camera lady (who is also my mother)? Check. Sunscreen? Uhm, what’s sunscreen?


I made the jump from baby booties to Keds in my early childhood.  These days, I’m looking for the coolest shoes in the world along with the most comfortable shoes my hard-earned money can buy. But back then, on my 5- and 10-year old feet, all shoes were comfortable, and my dad determined where we were going to shop (it was his hard-earned money, after all), so my only job was to pick out a color.

Whenever I got a new pair of kicks, whether they were school shoes, church shoes, or what people in the East called sneakers (we preferred the term tennis shoes, pronounced tenna-shoes), I’d of course, wear my old ones to the store.  After making my selection, the salesman would ring up our order, and ask me the magic question: “Do you want to wear them home?” He may as well have been asking me if I wanted Catwoman to make me a PB&J and watch The Flintstones with me. “Yes!” I’d smile up at him. He’d put the old ones that had waded in creek water, tracked through mud, and had a thousand games of kickball on them inside the new shoebox, which was basically a footwear coffin. Those shoes were dead to me. I wore the new shoes out of the store and never looked back.

In early elementary school, I’d wear Red Ball Jets – the big-kid-looking high tops that resembled the Converse canvas basketball shoes I would eventually sport in high school.  On the Born to Run album cover, I couldn’t see the shoes that Bruce was wearing, but I always felt certain that they were the iconic “Chuck Taylors.” And if they were good enough for “The Boss,” well…

At prom, I slow-danced to Eric Clapton’s “Wonderful Tonight,” wearing a powder-blue tux and Frye boots.  I was rocking a haircut that might best be described as a “Danny Partridge.”  When I wore these boots, I felt taller, tougher, cooler.  Shoes were no longer just apparel. There was a sense of statement and attitude and personal viewpoint that could communicate anything from rebellion to conformity to affiliation depending on what I was wearing. After all, a black leather jacket does more than just keep you warm.

In my early professional life, wingtips told coworkers, clients and bosses that, although I was young, I was to be taken seriously.  I struggled to find a balance between what I could afford, what looked smart and what felt good.  Smart-looking shoes didn’t always feel good. Comfortable shoes often looked… well…a little too comfortable.  If I found shoes that were stylish and comfortable, they sometimes cost half a mortgage payment.  It was around this time that I started seeing my wardrobe, including my shoes, as an investment.

I took the leap from cheap kicks to well-made shoes with Rockports, a particular model, if memory serves, called RockSport, and I never bought throwaway shoes again.  They were black, light as a feather, with an elegant outer shape and rubber soles. It was business up top, party down below.  A bit pricey for my 30 year-old self, but the comfort and style made ‘em worth every penny. I had a mini-epiphany: if a pair of men’s shoes isn’t worth re-soling, are they worth owning in the first place?

Since crossing the bridge to “better shoes,” I’ve owned black-and-white Johnston and Murphy spectators, saddle shoes, cap toes, wingtips, loafers and oxfords of black, brown, cordovan and even blue. I’ve bought walking shoes and running shoes. I’ve slipped on comfy Doc Martens and walked my daughter down the aisle in Allen Edmonds.  I thought I’d seen it all.

Then one day, while procrastinating on a writing deadline (like I’m doing now), I Googled something like, “most comfortable dress shoes, men” and scrolled a couple lists before seeing Samuel Hubbard shoes.


They had me at hello. Dope-looking designs. Mind-blowing colors.  There’s no way they’re comfortable, right?  Then I did some reading.  Turns out the guy who was at the wheel of Rockport when I was buying them has created a new brand. This brand. Okay, now I’m reaching for my credit card.

I started with The Founder in chestnut, quickly doubling down on The Free in ocean. I’ve found them to be light, stylish and foot-friendly. They’re shoes that can take me from work to walking to whatever without my having to change.  Great quality leather, and a wide variety from slip-ons to hiking books to dress-for-the-office shoes.  And the comfort is exactly what I expected given this brand’s lineage and heritage.  It’s like finding out the horse you just bet on had Secretariat in his bloodline. Giddy-up!

I’ve got two more pairs on order.


Brian P. Cleary is an American humorist, poet, United States patent holder, inventor and author. The bow-tie wearing children’s author is best known for his books that explore grammar in humorous ways written for grade-school children. To learn more about Brian and to see his work, click here

Kicking it with the kinder in Wiesbaden, Germany in Doc Martens slip ons during a book signing abroad.