Celebrity Stylist Ilaria Urbinati on Dressing Hollywood's Hottest Men: They're 'Down to Play'

Celebrity stylist Ilaria Urbinati, who works with some of Hollywood's hottest men, is opening up about what it's like working with stars including Ben Affleck and Chris Evans (with whom she had "such a blast" working on his PEOPLE's Sexiest Man Alive cover last fall).

In an exclusive interview with PEOPLE, the 43-year-old stylist, who recently made the The Hollywood Reporter's list of the 25 Most Powerful Stylists, revealed what it's like styling an A-list star.

"In a regular, non-awards season month, if we aren't in fittings, my team and I are doing pulls constantly — either making selects from images and having things shipped or running around to showrooms in L.A. or boutiques on Rodeo [Drive]," she explains.

Urbinati also talked about working with brands and creating custom looks for big events like the Met Gala or large movie premieres.

"Essentially it's a constant game of chasing clothes. The more options I have to play with in a fitting, the more creative I get to be. Then it's like playing dress up with the client," she tells PEOPLE.

"The goal is to keep their looks always evolving while staying true to who they are," she adds.

She also takes into consideration who they might be standing with; for example, Ben Affleck might be posing with his wife, Jennifer Lopez, who is always pushing fashion boundaries. For Affleck, then, "I just stick to classic, elegant, timeless looks," she says. "Can't go wrong there."

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Awards season is when things can get really wild, and a client may be photographed several times a week — so there's good reason to mix things up. When asked if it takes some convincing to get her clients to wear unique looks like pastels or patterns, Urbinati says it's not hard at all.

"A lot of these guys are down to play," she reveals. "They want to be bold." But Urbinati does admit it's important to make sure the actors feel like themselves.

"I like to push my clients a little bit out of their comfort zone, but I do think it's important for them to feel like the best version of themselves," she explains. "That's gonna look different for each one of them."

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She names a few examples of actors who push the limits — and look good doing it.

"The reason someone like Donald Glover looks good in all these bold looks is because he's so comfortable in them, so he exudes confidence and swagger," she says. "Otherwise it wouldn't work."

She continues: "Or someone like Barry Keoghan, he's young and into fashion and excited to play — so we can go there and we make it fun. It's not that deep. We don't make it too serious. But I'm equally as happy to just go super elegant and classic with a client who feels their best in that."