After an enlightening conversation with Karim Rashid about sneaker history, technology, and design trends, and inspired by his work for the Out of the Box: The Rise of Sneaker Culture exhibit at the Bata Shoe Museum in Toronto, we were interested to find out what the heavyweight designer would put on his own list of favorite sneakers. Rashid named many of his own designs. And as the five selections below suggest, his focus on technology and digital culture rarely wavers.

Rashid tells us why he love each shoe in the captions below.

Fessura Mirror
"The beauty of the Fessura shoes was the tops can be changed and come off the molded, soft, flexible bottom. The bottom can be worn separately for going in water, etc. I designed 40 different tops to interchange with the bottom molds."

Fessura Hi-Fi
"I love these updated Chelsea boots and the minimal design with bright accents of color. High tops were always my fave."

 Kromo for Sully Wong
"I always loved the simplicity of desert boots. I realized that there were none on the market made from leather that were interesting. So I made a minimal version, with very soft special printed leather patterns of my belief in the new global ornamentation I call digipop, and made them super comfortable and highly crafted."

Melissa Dynamik
"These shoes were co-injection molded. It is a robotically made running shoe that you can wear in the pool, the shower, anywhere."

Pro Keds Royal Skyhawk
"I found these on eBay, my favorite store on the globe. You can find a lot of amazing design objects online! I’ve even purchased and sold a vintage Avanti car and a house on eBay."