Reading · Journeys with Jay

I recently prepared to mop a mudroom, a small entry-area with a bench seat positioned under a large front window with three lower compartments each containing a basket holding spare shoes. The shoes that I normally wear are either kept at the front door or the back door including my current running shoes, an old pair of sneakers for yardwork, a pair of flip-flops to wear when letting the dog out, and some summer sandals. While initially preparing to mop, having to rearrange some of these items caused me to realize that I now own a lot of shoes.

Years ago while living in the city I had only one pair of sneakers that I wore exclusively. A friend told me that I needed a pair of actual shoes, that wearing sneakers is for suburban dads. He is now, coincidentally, a suburban dad. Working as a hotel bellman at that time, I was required to wear black wingtips for work, usually Rockports that could be picked up at Berkeley Shoe a few blocks down the road from Boston’s Marriott Copley Place. When my Rockports wore out, I would have them resoled. Marriott was incredibly stringent regarding its dress code in those days. I was once told after showing up for a graveyard shift that I could not work because I was wearing white socks. The hotel sent me out at midnight to find black socks. With a Store 24 nearby on Boylston Street, I managed to score a pair of black socks rather quickly and was still able to clock in at a respectable time.

My first year as a middle school teacher I typically wore a bargain pair of brown leather shoes that I picked up at Filene’s Basement. They were the only shoes I had with me one morning on a weekend trip up to Rockport. We walked all over town including all the way out to the end of a jetty at the tip of Bearskin Neck causing me to gain a whole new respect for those questionable brown shoes. During the holidays that year, I was given a pair of Timberland Chukka boots from the CambridgeSide Galleria Mall, well-made comfortable shoes that I could wear around the city and also to work. I ended up wearing those boots everywhere, eventually having them refurbished at a cobbler in Arlington just north of Boston. The school principal where I worked, frighteningly similar to Steve Carrell’s character from The Office in more ways than one, stepped out from behind his desk one morning with what I think he meant as a compliment. “I was thinking of wearing my shitkickers today,” he announced to the whole office while admiring my boots, to which I had to comically respond that they were actually my nicest shoes.

My initial discovery of eBay during those years meant buying cowboy boots, salvaged footwear in the spirit of old western movies where a pair of boots might be taken off some poor deceased character who would no longer need them. Once set up on a blind date in the city, I decided to wear a pair of cowboy boots that I had recently purchased not thinking about the multiple blocks that our small group would need to walk down in order to get to our destination, a series of city blocks that I “reckon” would be more appropriate for comfortable walking shoes rather than footwear meant for ambling into a saloon. Needless to say, my prospective date was hardly impressed, the boot situation being further compounded after downing a few drinks. Those boots were quickly gone, just like my date.

I still have a pair of black dress shoes that I bought many years ago. Hardly worn, the shoes were purchased to attend a wedding at the Scituate Harbor Yacht Club in the small coastal town of Scituate, Massachusetts. While having breakfast the morning of the wedding in nearby Brant Rock Village, my date told me to spend the day finding not only a pair of shoes for the wedding, but also a suit that would match her dress. I quickly came across a brand new black suit at a relatively high-end consignment shop in the town of Cohasset for $13.00 and then stopped by Marshall’s on the way home where I found shoes on sale for $15.00. Our Carrell-like principal, a man who prided himself on being a relatively snappy dresser, approached me at the reception. Impressed by my threads, he was in disbelief when I told him that I paid only $13.00 for the suit. I still have both the shoes and the suit, a combination that I sometimes throw on for formal occasions that still looks fantastic, especially if the suit’s particular style happens to be ‘in’ at the time.

Years ago I picked up two pairs of brown shoes made by Clarks from an outlet in Merrimack, New Hampshire. Both pairs were extremely comfortable, shoes that felt more like sneakers. I wore both pairs until they had cracks in their soles making my socks wet on rainy days. Neither pair could be resoled. I searched endlessly in an attempt to replace those Clarks looking at various stores and also on the internet. I ended up ordering a few Clarks models that should have been adequate, but attempts to replace those shoes never felt quite the same. As a result, I still have a few pairs of Clarks shoes, old worn out boots and new shoes that were ordered to replace a pair that had been tossed.

Still looking to find those elusive Clarks, I once found myself in the shoe section of the Nordstrom Rack store in the town of Braintree, Massachusetts. While I didn’t find any Clarks at Nordstrom’s, I did pick up a couple of pairs of fair-priced shoes that appeared to have potential. I bought a pair of pull-on Timberland boots and also a pair of Chukka boots reminiscent of those great shoes from the CambridgeSide Galleria that I originally wore while still living in the city. Both great pairs of shoes, I almost never wear either.

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More than a decade ago I owned a pair of Hi-Tec hiking boots that I absolutely wore into the ground. I replaced them with a bargain pair of Merrell hiking boots that I also wore into the ground, although I still keep those old Merrells around the house for doing exterior carpentry or painting. In an attempt to replace my old boots a few years ago, I chanced upon a pair of Timberland hiking boots that happened to be on sale. Over time I began to wear the Timberlands to work during the winter, the shoes eventually becoming a comfortable favorite of mine. Coincidentally, they are the same Timberland boots as the kind once favored by old friends Gabrielle and Alexandra from the 4th floor of my building in Boston’s North End, comfortable walking boots that they both wore almost exclusively to get around the city.

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A few years ago I was given two pairs of Allbirds, one pair of black high-tops and a pair of black low-tops. I wore these Allbirds while teaching for almost an entire school year receiving more than a few compliments. By June I started to wonder if my lower back and hip pain might be related to the flat-footed nature of these shoes, although most joint pain in my workplace has been prospectively traced back to the rudimentary floors that were installed at the time of the new building’s construction. Although I took my Allbirds out of circulation for a year, I am excited to begin wearing them again in September.

I strangely have many different pairs of flip-flops and sandals, although I generally choose to wear only sandals with crossover straps that can be tightened. My first sandals were given to me as a birthday present while living in Somerville in 2003. Years later I replaced those first sandals with several similar pairs of cheap Filas from Kohl’s. Now almost a decade old, my last surviving pair of Filas has seen better days, sandals that are now only good for dipping your feet in the ocean or wearing while in a kayak. A few years ago I bought a pair of Nortiv8 sandals figuring that if the Filas lasted a decade then this pair might last forever, forgetting that I had already bought a pair of high-end Tevas the year before. Additionally, I still have two pairs of flip-flops that I grabbed at the end of the summer years ago. One is a standard pair of flip-flops with impressive cushioning. The other is what kids now refer to as slides, a red and black pair of rubber sandals that appear to be comfortable but ended up cutting the tops of my feet when I wore them walking on a Cape Cod beach. A pair of flip-flops that I actually do wear I bought at Kohl’s way back in 2010. I liked them at the time because they looked old and worn out. Now I prefer them because they actually are old and worn out.

As a runner, I still have a lot of sneakers around the house. I generally use my New Balance shoes exclusively for running. Some sneakers have fallen into the category of work shoes, like my old 860s that I wore while moving an entire tree that had been cut down in my yard during the summer of 2024 by a dysfunctional lumberjack, shoes that were essentially destroyed although they are still great for weed-whacking, mowing the lawn, or letting the dog out. I have several pairs of New Balance 680s still brand new, shoes that I purchased while on sale in an attempt to stock up, although I have since switched over to New Balance sneakers with foam soles such as the 880s, my new favorites.

I’ve come a long way from owning just a single pair of sneakers, although it probably does no harm to hold on to a few extras, advice I may have gained from my dentist decades ago when my wisdom teeth were starting to come in. When I asked with trepidation if they should go, he laughed. “Not a chance,” he said. “Someday they might be the only ones you have left.”

NOT READY TO GIVE THESE SHOES THE BOOT

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