Manny Santiago, Spanish Mike and Yosef Ratleff Talk Skateboarding and Style

Since its genesis, skateboarding has been inextricably linked to style. So when we hooked up with JD Sports to put together some live rooms all about giving a glimpse into different communities and their relationships to style (among other things), skateboarding had to be one of the cultures we did a deep dive on.

We tapped Ben Oleynik, founder of the skate brand Grand Collection, to sit down with a few big-time names in contemporary skateboarding: Manny Santiago, Yosef Ratleff and the legend Spanish Mike.

Shop the looks from the stream below, and read on for cool insight from the hour-long live room, during which they discussed their entries into skateboarding, developing style and what's to come.

Ben began the chat by asking everyone how they got into skateboarding. From family inspiration to other introductions to the community, the myriad of answers all revolve around the infinite possibilities represented by skating.

Manny, who joined the room hot off his first Olympic appearance in Tokyo, called his intro to skateboarding natural. "It found me," he told Ben, before describing seeing people skateboarding: "I realized they were having so much fun—and I want to have fun." Plus, skateboarding is so unique and individualistic; people can do so many different things with their decks. "There's so many possibilities with skating," Manny added.

Spanish Mike is one of the most well-respected videographers in the game, so naturally, they talked videos for a bit. For Yosef, who Ben referred to as "YoYo" throughout, the video "Baker 3" jumped to the forefront immediately.

These guys are pros, so they also discussed the moment they each realized that skateboarding could be more than just a hobby and how they've made careers out of the lifestyle in different ways. For Spanish Mike, his decision can be traced back to one of the other folks in the live room. Ben asked him when he knew he could make a career out of skateboarding: "The day Manny called me to come move to California," he revealed. He then dove into how he started making content, saying: "I was vlogging before vlogging was a thing."

Naturally, the four friends spent a bit of time talking about style and how they think about what to wear when they go out to shoot a part. Yosef spoke on how confidence plays into what you wear: "You just gotta own it [...] You gotta just be comfortable with your style and how you put yourself out there. And if you got that confidence, that's definitely gonna show to other people."

And Manny, who's well-known for his eccentrically dyed hair and glowing smile, added: "Style, it identifies with who you are [...] Your fit and your style is how you're feeling at the time. How you feel about yourself. And self-love. How you wanna portray the energy you have inside."

Spanish Mike emphasized the importance of comfort and being cozy, with Manny emphatically adding, "That's JD Sports right there. JD Sports got you comfy!"

Although these guys are all involved with skateboarding in different ways, tons of the advice and insights throughout are applicable to numerous pursuits. Whether you're a skater, content creator or still looking to find your passion, watch the whole stream and get inspired:

If you missed the first two streams, make sure to check out our conversation with gamers and emerging hip-hop talent. Style is different for everyone, but each of these groups has managed to find success in their respective lanes—we can all learn from every last one of them.