Iconic Shoe Repair Shop Still Thriving

Sidney Wilson Jr. is the owner of Sidney & Son, a shoe repair shop, once owned by his father; it has existed on Market Street since 1955.

By Hadassah Deleveaux (née Hall)

It’s an iconic shop…one of the few indigenous, old family businesses still standing on Market Street. Sixty-six years to be exact. It’s my go-to cobbler shop, over the hill and I recently found it necessary to stop by.

I can’t stand when shoes begin clacking because of missing or damaged heels, so I needed to rectify the problem. After all, if the shoe itself is in good condition, what’s $10 to save a pair?

I pulled into the tight parking space that could probably fit about three to four vehicles. As I walked in, an elderly gentleman was making his way to a chair. Shortly afterwards, I realized he was there to chat and chill, but not for service. Sidney & Son is that kind of place. The owner, Sidney Wilson Jr. was born and bred in the area, and is friendly with its residents.

Built in 1955, Sidney & Son is located on Market Street.

“I was born through Rupert Dean Lane, Bain Town and from I was born, I was here. From I know myself, I was observing and doing something in here. I have done this all my life. This is my love,” said the second-generation cobbler.

“I know everyone in this area. All my life I was on Market Street. I have seen the turning around of Market Street. Time brings on changes,” he said matter-of-factly.

And lots has changed since Mr. Wilson attended St. Agnes Preschool, Western Jr. (now C. R. Walker Senior) and then went on to St. John’s College, which back then was up the street near Government House in the north. The preschool has long shut its doors and St. John’s has long moved to the Stapleton Gardens area. Further, many of the other shops he frequented as a child are now abandoned buildings or have been turned into other businesses.  

Shelves of shoes in the shop which has existed for decades.

Sidney & Son is that white one-storey building with the red trimming, bars and door, just north of Taylor Street.  His father Sidney Wilson, started the business with his brother Thaddeus, but eventually decided on a solo venture. Initially, his father was renting, but in 1955, Sidney & Son was opened at its current location – on property he purchased.  

Sidney Wilson Jr. proudly holds a photo of his father, Sidney Sr., who was the brainchild behind Sidney & Son.

Upon walking up to the counter, I saw shelves littered with shoes. However, the workshop was still clean. You could tell there is a method to the shoe madness. I also saw very old machines; one was a finish machine, which Mr. Wilson said is over 60 years old and the other was a stitching machine for shoe soles. Both were still getting the job done.

Stitching machine.
This finishing machine is over 60 years old.

Still evident in the store are other pieces of history from a bygone era. For example, on one of the higher shelves, I spotted a pair of platform shoes with the name ‘Keith’ inscribed on one foot and ‘Lover’ on the other. They were exceptionally high. I asked Mr. Wilson about the height and upon measuring one foot, it was a whopping 7 ½ inches. It reminded me of a few of my family photos with men in platform shoes; he mentioned that men wore platform shoes in the 1970s.

On another shelf was an old record player of which Mr. Wilson proudly showed me the record collection he still has in the shop. And sitting in a corner was a cash register; he said it was in the shop from the days of five pounds, shilling and pence. My mother would know about that!

“A penny could have bought bread and sausage, five pounds could have bought property in the Five Pound Subdivision in the Kemp Road/St. James Road area,” he said, as he pulled out a few pieces of the old money still in the shop.

In another corner was a vintage, but lovely double shoe shine chair. My mind immediately went to my father’s youth. I was told he was a shoe shine boy for a while.

Platform shoes, once owned by a man name Keith. It’s 7 1/2 inches high.
Record player from back in the day.
Mr. Wilson proudly displayed an old record collection.
Iconic cash register, still sitting in the shop.
Mr. Wilson pulled out money used before my time.
Vintage shoe shine chair. There’s still something beautiful about it.

Meanwhile, I asked Mr. Wilson what keeps him returning to the business, which is a staple over the hill. He answered, “The people. The customers. I have loyal customers. The whole island has supported me. I even have customers from the out islands,” he stated.

In fact, Mr. Wilson learned his work ethic from his father. He is open year-round, closing only for holidays and Sundays.

Organized chaos.

“Before the pandemic, I would close on Mondays for personal business, but if there was nothing to do, I come to work. And work is just not just fixing shoes; work is cleaning the yard, keeping the place clean and sanitized more than ever before,” he stated.

Questioned as to who will take over the business from him, he hastily replied: “Only God knows.” Back in the day, his father did train other youngsters; however, they did not want to be a part of the cobbler life.

Mr. Wilson too was a bit shaky about getting into the industry during his youth.

“I ventured off, but I still would come and learn the trade. My father told me one day it would be mine, so put some interest into it. It was hard because he was a strict person, but it paid off, and here I am today because of what he did,” he acknowledged.

18 thoughts on “Iconic Shoe Repair Shop Still Thriving

    1. Hi Ernestine. Please forgive me for just responding, almost a week later. Thank you so much for reading the post and yes, do catch up on the other articles. It has been my pleasure featuring each individual or business!


  1. I enjoyed the article on Mr. Wilson’s shoe shop. I always visiting to have heels repaired on shoes I like. In fact I have a navy blue pair to have done as soon as I can get to Market Street. Mr. Wilson’s service is much needed. So Hats off to the Cobbler, for Excellent work.

    Liked by 1 person

  2. I really enjoyed this trip down memory lane with Sidney Jr aka Junnie. Keep doing what you’re doing. Am a 70’s baby and I LOVE learning about the history of our country especially over the hill. Great article.

    Liked by 1 person

    1. Thank you so much Ulean! I too have come to LOVE learning history. If I had this type of love of history in my high school years, I would have studied it as a subject once I reached 10th grade.

      And I will continue to do what I’m doing. Sometimes, I wonder, “Who’s reading this?” This kind of writing is not sensational; it’s not gossip, so it’s not what interest many people. However, this particular story has been shared some 234 times on Facebook so far. It seems to have really resonated with people.


      1. Yes it has. Looking at ALL the comments this story has sparked some interest in alot of folks including me.

        Once again keep up the GREAT stories of yesteryear. May God continue to bless your hands with writing.

        Liked by 1 person

      2. Thank you so much! Honestly, I’m surprised at the traction it has gotten, especially on Facebook. It has truly warmed my heart. I have since called Mr. Wilson and he said he has received so many calls!

        Further, thank you for that blessing. I receive it in the name of Jesus. God gets the glory. Writing is my gift and I absolutely love it. This blog is an avenue of using my gift in a meaningful, positive way.


  3. Oh man… this article makes me now just wanna stop in for a quick sniff… I still remember the distinct smell of… leather… glue…etc. Always just a cozy and welcoming feeling.

    Thanks for this!


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