Street Dapper Kings 2018: How working in fashion helped Tommy Esguerra expand his own vision on style

Is there anything Tommy Esguerra won’t wear? Even the model/actor himself can’t tell where he’d draw the line. “Like gold hot pants? Sure, why not?” he tells us with a shrug before flashing that smile that has been on its share of billboards and ad campaigns.

The California-raised Esguerra used to have a more careless approach to dressing up, given the sunny, California surfer culture he grew up in. However, once he was thrust into the modeling industry upon his return to Manila, he began to see the many possibilities that dressing up can open to him, including a more authentic self-expression. “I had to pick up my game and re-invent myself. I got exposed to a lot of fashionable people, and they all had a hand in guiding me towards finding my own style.” One of the people he credits is Garage‘s editor-in-chief Rey R. Ilagan. “I always see him wearing or carrying something really stylish and of good quality that I haven’t seen on anyone else yet, so if I could raid anyone’s closet, it would be his,” Esguerra says.

Suit by FRANCIS LIBIRAN, shoes from PEDRO

The 24-year-old claims that even after almost six years as a model and a celebrity, he still gets those light bulb moments when it dawns on him how an unconventional piece of clothing or accessory could work with a look. “Oh, I get them all the time,” he emphasizes. “Fashion constantly changes. Just when I think I finally got a look down, in a month or two, there’s something else to learn, something new to try. And I better keep up with the scene or else I fall behind.” The turtleneck top, for example, has been a recent favorite. “And then I hear that it’s on its way out already. Like, what?! But I love turtleneck sweaters!”

He remains good-natured about the “pressure” to keep pace with the times, though, as he recognizes the help that stylists provide to help him keep his look sharp and current. To get prepared for a day of public appearances and maybe 10 outfit changes, Esguerra would take photos of his outfit selections in the morning to get feedback from his friends. “It’s not just me, you know, but it does take a little work, a little preparation to get yourself ready.” From his early days of looking at his wardrobe without a single clue on what to wear, he now has a system down pat that allows him to get out of the house in style and on time. “I’ve gotten it down to an average of 10 minutes,” he says. “But it took me a long time to learn the system that works for me.”

Shirt, jacket, and pants, all from SMYTH at SM YOUTH

One strategy he found helpful was getting his closet organized according to the different styles he usually gravitates to, from formal to street chic and casual to something a little more unusual. Esguerra also took to heart a valuable tip that he has learned from other celebrities about building a good foundation for his wardrobe: “You get the basic pieces in four to five neutral colors,” he says. “For example, get two button-down shirts in white, two in black, two in blue, and maybe another pair in gray. Then three or four different-colored jackets: black, dark blue, gray, and another neutral color—maybe white, if you feel like it. Not too many sweaters or pullovers, but if you’re going to get some, get them in four to five plain colors. Starting with the basics will make your clothes so easy to mix and match. That’s where I started, and I just built up on it.”

And now, he’s so comfortable in his own style that wearing lamé hot pants wouldn’t be a big deal. “You learn as you go. Just keep your mind open, and have fun with it.”