For many people, shoes and clothing are a means to keep comfortable and warm, but for senior Jack DeSimone, with vivid air brushed patterns on his once-white sneakers, they are a lifestyle.

DeSimone has been infatuated with sneakers since fifth grade, and has bought and sold them for years. He has customized around 30 pairs to date for both himself and others, and he sees them as a central aspect of his personality.

“I’ve always loved sneakers,” DeSimone said. “Sneakers have always been a part of me.”

DeSimone pursues his passion by constantly searching for footwear on platforms like eBay, Mercari, Grailed and GOAT to either resell them for a profit or keep for his personal collection.

“During school hours or at home, I’m always on those apps looking for stuff to buy and sell because it’s fun and easy,” DeSimone said.

His interest goes far beyond buying and selling, as DeSimone customizes shoes and clothing. In fact, he runs several Instagram accounts including @vivicustom, where he sells his own customized footwear with fellow senior Beau O’Beirne from Saint John’s High School. Together, they have made shoes such as Louis Vuitton Air Force 1s and sunset-fade Old Skool Vans. According to DeSimone, their process is quite complicated and labor-intensive.

“We use a stencil, and we’ll take an all-white sneaker and put the stencil over the white part,” DeSimone said. “Then we use an airbrush to spray the sneaker, and we also put tape all around. Then we spray paint it, then take the stencils off, and the pattern will be there.” 

DeSimone also runs @_jackscloset_, where he resells his uncustomized sneakers and streetwear he buys.

“I started finding clothes for cheap online and buying and selling them because it was faster and easier [than customizing],” DeSimone said.

DeSimone was originally inspired to customize shoes by the YouTuber Marko, as well as  several other influencers including Rick Owens, Drake, Bloody Osiris and anyone else associated with New York fashion.

“I like a lot of New York fashion just because it’s really crazy and there are lots of cool, crazy pieces that are developed by people,” DeSimone said.

None have been quite as influential as Jacob Crain, the older brother of DeSimone’s girlfriend, senior Amanda Crain.  

“When I started dating Amanda, I met Jacob, and I just really liked his clothing,” DeSimone said. “I’ve always liked clothing, but I’ve never had the confidence to buy expensive clothing. He was someone who influenced me and showed me that you could always get your money back if you try to sell the clothing.”

However, Jacob isn’t the only Crain involved with DeSimone’s love for fashion and shoes. Amanda helps him organize, take photos and market each product. Consequently, she has gained an appreciation for the qualities DeSimone possesses that allow him to be so successful.

“He’s very dedicated to [his business] and very passionate and driven,” Crain said. “Even if someone is negative about it, he doesn’t really listen and knows he can make a profit and keep going with this.” 

In the future, DeSimone would like to pursue a career in marketing because he feels it would be a safer path to take than reselling clothes and sneakers. Yet wherever the road leads, DeSimone will always have a passion for fashion.