Josh Strickland

Recording artist, actor and TV personality; age 27

What he’s wearing now: Abercrombie & Fitch jeans, Wet Cement shirt, Benetton scarf, David Yurman ring, Scott Kay bracelet.

Style icons: Ralph Lauren and Tom Ford.

With his rising-star status solidified, Strickland recently indulged in a few A-list purchases. “I never imagined I would buy real Louis Vuitton accessories,” he says. “Growing up, my style was all over the place. I characterized it as preppy Southern. Now when I’m in the recording studio, I sway toward sweats and sneakers so I can stay comfy and warm.”

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Hello, I’m Tim. Over my 15-year career in the fashion and hospitality industries, I have worked as a stylist to numerous celebrities and industry leaders, including a stint as the personal assistant and stylist to Sean “Diddy” Combs. I’m serious about dressing well. In fact, I design all of my own shirts, suits and formal wear, working directly with my tailor, visiting his workshop twice a year to oversee the construction, cut, fit and finish of all my clothes.