Alexandra Wentworth in O Magazine

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Plenty of Flak
"I think I take risks in life more than in fashion because I'm terrified I'll be made fun of for wearing something flashy," says Wentworth. These urban fatigues—a military jacket (Smythe, $650), tank (7 For All Mankind, $68), and cargo pants (Rare Donna, $254)—felt right to her, even as a head-to-toe uniform. "I wasn't sure about cargo pants with high heels, but they look incredibly feminine together," Wentworth says. "Jumping over fire in them is a little difficult."

Dog tag necklaces, David Yurman and Tom Binns for Disney Couture. Pin, Ben-Amun by Isaac Manevitz. Cuff, Vita Fede. Ring, Kardashian for Virgins Saints and Angels. Belt, Melamed. Shoes, Guess