Josh Segarra: Sweatpant Swagger

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Josh Segarra lives his life in sweatpants — particularly around the holidays. “No shoes, no combing the hair, no nothing,” Segarra says with a laugh of his holiday style plans.

“I am into style; I like being up to date and I like things that fit well, and I do read up on GQ and Esquire,” says the On Your Feet star who plays Emilio Estefan in the musical based on the Estefans’ story. “But what do I live in? I live in sneakers, sweatpants, hoodies, and baseball caps. But they’re all fitted. They all go well together. I’ll toss a leather jacket on top of it.”

However, Segarra does take a little credit for some of the latest fashion trends. “Now that sweats are in, are you kidding me?” he says. “That’s what I tell my wife. I’m so fashion forward you don’t even know dude! They’ve been trying to catch up with me.”

But growing up in Florida, a sense of style was ingrained in him from an early age, and Segarra credits his Puerto Rican heritage with his commitment to “looking good.” “I’m a Latin kid, being well groomed was part of my upbringing! If you wore something once, it was in the wash,” he says, adding that he does enjoy dressing up when the occasion calls for it. “I like doing things that are clean and sharp. I always say that my spirit animal is Pitbull because I love the way that Pitbull dresses. If I was a man that lived in suits, I would be wearing suits just like him. He looks like he just got off a boat, and that’s how I want to look.”

The Glam Squad
Playing Emilio Estefan is very personal to Segarra, who grew up listening to the Estefans’ music (and may have shook the maracas to “Conga” in a make-your-own music video at a theme park with his family when he was little). So for opening night, he wanted his style to tell a story as well. While talking to his barber Robin Capili, who works out of the Sally Hershberger Salon downtown, Segarra mentioned that he was searching for a look, and Capili recommended his friend, Angel Ramos, who has family in Miami who know the Estefans. Ramos, through his line Angel Bespoke, dressed Segarra for the openings in Chicago and on Broadway. (The red jacket in the photos is the one he wore for the New York opening.) Segarra even invited Ramos and Capili to the Broadway opening. “What kind of guy would I be if I’m over here without the two guys that made me feel like a million bucks?!”

A Bearded Man
While Segarra has been going to Capili for about four years, the barber became indispensable when Segarra had to grow out his beard for On Your Feet. He enjoys having the facial hair and keeps it tame using a boar bristle brush but doesn’t do much beyond that. “When I’m not in the show, I live more in scruff,” he says. “When you have to manicure yourself every day for work, when you’re not working, you have to let it all go.”

Team Spirit
Baseball caps and jerseys take up a large portion of Segarra’s wardrobe. The two teams that he “bleeds with” are the New York Jets and the Orlando Magic. “I grew up with the Magic,” he says. “I have the NBA League Pass and I watch every game, even if it’s on in the background. That’s why I love my wife; she lets me do that.” Over the years, Segarra has been an invited guest at Madison Square Garden a few times, and on his first visit, he made a slight fashion faux pas. “The first time I go to the Garden, they tell you there’s some guidelines. You need to wear nice clothes, no jeans, nice shoes,” he recalls. “I invite my best buddy, and we both show up in shirts and ties and slacks. Our hair is combed. And of course, we get there, and everybody else is in cool jackets and baseball caps. So we’re sitting in our nice business casual outfits not wanting to embarrass ourself at the Garden. We felt like two eighth graders at our graduation.”

Who Wears Short Shorts?
When Segarra makes his entrance in On Your Feet, he’s wearing some of the shortest white shorts you can imagine. “I love it because when you’re onstage, you already feel naked, you already feel vulnerable,” he explains. “You have an entire audience of people staring at you. Imagine that feeling and then put me in some short, white shorts and then put them on a dude that used to be chunkier growing up. My legs are so big and my butt is so big—what am I doing up here! Every night before I walk out onstage, I go, here we go Josh.”

Doggy Style
Segarra has a little fashionista in his life: his Morkie puppy Suzy. “She loves wearing clothes!” Segarra says. “She has a Jets jersey that she loves wearing on Sundays.” (She even got an elf costume for Christmas.) For their first winter together, Segarra bought her a down jacket and little UGG-looking boots, and when his wife asked how much he had spent on their eight-pound dog, Segarra advocated for fashion. “She has to be protected and she has to look fly!” he says.

Watch It
Segarra’s go-to accessory is a nice timepiece, and he’s wearing a different watch with each of the looks in this shoot. “Watches are something that I’ve been collecting over the years,” he says. “For my wedding, I got a watch from my aunt, my parents, and my wife.”

A New Year
Segarra isn’t one for New Year’s resolutions, but he is excited to see what 2016 brings for him and his family. “I’m a sensitive soul so I’m always trying to figure out how to make the next year alright,” he says. “This year has been a big year; I’ve learned a lot about myself. I know that next year is going to be a huge year so my resolution is to keep my head on straight. I’m about to be 30. I got my support system. I got my family behind me. We’re ready to go.”

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