Leo Baker Just Wants to Be Comfortable

Leo Baker’s closet isn’t just a closet. It’s a closet, a sewing room, an art studio, and a music space. Nike SB jackets hang by a Singer Heavy Duty sewing machine, all beneath mounted guitars. The menagerie is due to more than just limited NYC square footage. “That's all part of the creative process,” explains the 31-year-old pro skateboarder. “If I get really stoked on an outfit, then it gets me inspired to skate.”

As a trans man, Baker always had a defined approach to how he wanted to express himself, even if that didn’t fit molds. Through his brand Glue Skateboards, launched in 2020, he's developed an active role in designing clothes in addition to his lifelong passion for streetwear. “It's just fun to make clothes,” he says. “It's something that I've dreamed of doing for a long time, so I'm sort of able to dip my toe in there, and that's been really awesome.” But it’s not altogether a new step. Baker has been honing his construction skills behind his sewing machine for years. Almost everything that enters his closet passes beneath the Singer machine needles first, whether that’s for aesthetic or logistical purposes. When a new package of Nike SB clothes arrives at his door (a brand sponsor of Baker), “I'll have a field day of fucking around and tailoring all them,” he muses. He’ll tailor a pair of pants, crop and taper a boxy top, or take an old shirt that doesn't fit well, and then sew the graphic onto something else, just mashing up the clothes.

Baker was tailoring before he was designing. Standing at 5’5”, almost everything is too long for his frame. Now, he’s making sure his pants have a single break on the shoe and an eight-inch leg opening, but years ago he was trying to erase the gender from clothing. The pro skateboarder landed his first sponsorship with Billabong at 11. That brand, and subsequent others, allowed for some flexibility but at a certain point, pushed girls' clothes on the tomboy tween. “That's how I got into sewing,” he says of his 16-year-old self. “I didn't want to wear, like, flared pants, so I learned how to taper my jeans.” Few 11-year-olds have such a distinct sense of self—but maybe that comes with knowing what you don’t like as much as what you do.

“When I was younger, age 12 and before, I feel like I was really solid in my identity and the way that I looked,” Baker muses. “And then I was trying to appease sponsors for a solid chunk of my life that made things feel super weird for a really long time. Now, I feel like I'm right back in that full circle. Yeah, I'm a boy and I wear baggy skate clothes, and there's really, really not that much else.” In fact, “baggy skate clothes” is how he initially described his aesthetic to me, citing early icons like skateboard Tom Penny as influences. When asked to expand, he puts it simply: “I just want to be as comfortable as possible.”

Baker’s closet is, unsurprisingly, built on the foundation of soft materials. This ranges from scarlet-hued Gucci basketball shorts to mustard Marni pants to Nike fisherman sweaters—yes, there’s a Nike swoosh in the cablework. He’s recently been in a Depop Givenchy hole, and he has the spoils–in the form of worn-in button downs and khaki pants–to prove it. But every now and then you get a wildcard. Perhaps that’s a pair of Nike x Tiffany Air Force 1’s or a fringed vest from his late rockstar father’s onstage wardrobe, which he wore unbuttoned to reveal his top surgery scars on a sunny day in Brooklyn. “I've never actually worn that before,” he reveals of the latter. “I like classic stuff—Jordan ones and blazers and stuff like that. Things that are just timeless.”