A Sitdown with Wesley's CEO

Owner, Bruce Wesley has been in the shoe business now for over 5 decades. He started at the early age of 9-years-old. Want to get to know Bruce a bit more? Sit down with him to get a behind the scenes view of Wesley’s Shoes with a Q&A session!

Q: How did you get started?

A: When most kids were watching cartoons on Saturday morning, I was moving shoe boxes in the stockroom. Every Saturday, I would report for work. I really started enjoying it and looking forward to it each week.

It was the 70’s and the shoes were bright, colorful, and exciting. The shoeboxes were like the album covers of the Era: bright and colorful. Soon I was not only shifting boxes, I began waiting on customers and to help Dad merchandise the store. I would escort him on buying trips. Back in those days, they were either held out in Arlington Heights or McCormick Place. We would shop for merchandise. I remember he would ask me which style I liked better. Of course, I would give him my opinion.

Soon I was doing the buying and merchandising for the entire store at the early age 12-13 years old. I also began to experiment with doing window displays and window trims. It looked like artwork to me. I could look at a window display and duplicate it in our windows. I spent many evenings looking at the Windows displays at Marshall fields, Kham & Nate’s and other prominent stores of the time.

Dad was always a forward thinker. He knew our store would need to relocate soon. By the late 70s, we saw the direction it was headed.

Q: What’s the best business advice you’ve ever received?

A: Sol Price, owner of Alamo Shoes here in Chicago told me “Just hang in there no matter how tough things get. Your time will come”. 

Q: What was your first paying job?

A: Ironically, I have never worked for anyone else except my dad. So I pretty much have been self-employed my entire life.

Q: What did you want to be when you grew up?

A: First I wanted to be in the Marines, only because I loved their uniforms. Then I wanted to be an Architect because I loved to create things. I even took drafting in High School.

My biggest dream was to be a basketball star. I ate, drank and adored early ball players like Dr. J, Walt Frazier.

Q: What is inspiring you right now ?

A: 2 things

  1. We were nominated by the Shoe Industry (Footwear News Insights) as the #1 Independent Shoe Store in Illinois and the Midwest. We were ranked #2 in the nation and just shy by 1 point for being #1.

  2. We are in the early stages of designing our Store in Hyde Park. We plan to relocate to part of the abandoned space left over by Trader Joe’s. This will give us street access for the very 1st time! We will be doubling our retail and storage space allowing us to expand our women’s apparel, athletics section and create a state of the arts atmosphere. The most unique store and shopping experience in the nation!

Q: What might people be most surprised to know about you?

A: I am a hopeless romantic.

Q: What is your motto?

A: “I don’t walk away from negative people, I run like hell!” 

Q: What is your favorite hometown memory?

A: Becoming a merchant in Roseland during the early 70’s. South Michigan Ave. during those days was an incredible mix of merchants. We had every store you can think of: J. C. Penny’s, Kmart, Sears & Roebucks, Old Fashioned Doughnuts, and many more. The best place was Gately’s People Store, it was like the Marshall Fields of Roseland. We were located right in the heart of it all.

 Q: Who are your 3 most coveted dinner guest dead or alive?


  1. Jamie Fox because he’s so down to earth, funny, cool and great business head. 
  2. Muhammad Ali. He was to me the greatest athlete ever. 
  3. My Mom: Oneida Wesley. She died when I was only six years old. I really never got a chance to know her. 


Q: What are your favorite tv shows or series?

A: Absolutely “The Good Fight”, A story about a black law firm and the day to day hustle and things it goes through. It’s also filmed in Chicago. I also got hooked on Ozarks and Breaking Bad, both crime series.

Q: What music is on your personal playlist?

A: Drake, HER, Daniel Caesar, Nina Simone, Bill Withers, The Beatles, Minnie Ripperton, Led Zeppelin, Roberta Flack, James Taylor and Eddie Kendricks.

Q: Where do you see Wesley’s Shoes in another 50 years?

A: I predict the Wesley’s name and brand will be as common and well known as Nordstrom‘s, Macy’s, or Dillard’s. I am setting the foundation for future generational wealth and growth and build on the legacy that my dad Alvin J Wesley founded.


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