Generation Cool – A Commercial Time Capsule


For the past 10 years I have been flipping and selling vintage secondhand items from furniture all the way to 90’s stuffed animals and almost any vintage clothing I can get my hands on. My main passion is reselling and collecting vintage clothing and have been doing so for the past 5 years and counting. Since relocating to Tucson in 2020 I instantly was on the hunt for a new location to shop, sell and or even trade with! After doing some local research I found out about a vintage reselling shop on Tucon’s popular Fourth Avenue called Generation Cool.  After seeing so many positive Yelp reviews, I decided to visit and see for myself what all the hype was about.

The first thing you’ll notice is the storefront, a bright red and white checkered pattern that can be seen from a block away. After stepping foot in the store, you are greeted by a staff member (the day I went I was happily greeted by Blake, the store manager) and then engulfed by hundreds of different products from vintage Nascar racing clothing and top designer jewelry to vintage pins and popular action figures like Batman, Mickey Mouse, Power Rangers, Mario Bros, Pokémon. The store walls are covered in fast food logos (Burger King, Jack in the Box, Mcdonalds, 7 Eleven, Circle K), clothing brands (Nike, Adidas, Harley Davidson, Big Dogs, Gucci, Louis Vuitton), and old cartoon characters (SpongeBob, Super Man, Scooby Doo, Teenage Mutant Nijia Turtles).

The shelves are stocked with toys that take you back to your childhood, deadstock baseball cards from your favorite players and teams, and other small accessories; as you can see from the picture above, my favorite is the Snoopy phone). Racks upon racks are filled with vintage sports jerseys, jackets, shirts, hoodies, pants, shorts and even custom-made shorts made out of 90s pillowcases and bed sheets. The store even has an old video game system with Pacman, Mortal Kombat and other classic games. It’s also free to the public and to customers who love to play it, especially the kids!

Coolness Personified: Slobby Robby’s Support for the Next Generation

Generation Cool originally opened in 2013. The store is owned and run by Robert Hall, or better known as “Slobby Robby,” a social/business influencer who has been in the vintage reselling game for the past couple decades.

I got the chance to meet Slobby Robby in person and it was even better of an experience then I could have expected. Off first impact Slobby was very well dressed in a loud New York Yankees uniform with an absurd amount of crazy jewelry hanging from his neck and covers his hands. He greeted me with a massive amount of energy and instantly started walking me through the entire store, sharing his vast knowledge about vintage T-shirts. Meeting Slobby Robby was a great eye-opening experience for this very small fish in the huge pond of the reselling community.

Slobby Robby volunteers at Sam Hughes Elementary School and teaches art, fashion, brainstorming, creativity, and he helps the schools do creative projects for the children. For example Slobby helps students create their end-of-year shirt (which is their replacement for their yearbook). He also teaches them creative arts. Slobby Robby “ It consists of them coming up with their own visuals, shapes, spaces that remind them of the year and then they will make their design come to life with spray paint and stencils,” he told me. “This gives them something positive going into the summer that they can wear, that also makes them feel good about themselves.”

In addition, Generation Cool likes to stay heavily involved in the Tucson Community by doing anything they can to make a positive impact. Some examples are being a part of Fourth Ave Merchants Association which supports a street fair that expands fully down Fourth Ave and is thrown every year in March. It supports its local businesses all the way to supporting the homeless and mentally ill by donating clothing and necessities to help those people have an easier time. Even the day that I visited the store, Generation Cool made a donation to Ben Bell’s which is a kindness movement that the store likes to support often and donates Generation Cool mystery boxes that are sold at an auction and all profits go towards the cause. Generation Cool is also a part of FAMA (Fourth Avenue Emergency Association).

My Take

Whether you’re a vintage collector or just a casual shopper that likes to browse, this store is worth checking out. The store is very welcoming and the staff can answer pretty much all of your vintage questions.


Jack Gay is a sophomore at the University of Arizona majoring in pre-business through the Eller College of Management.