Before: "I got into a rut," confesses Max, a paralegal. More like a mire—witness the boxy, too-big polyester suit, deplorable tie, and overly sculpted facial hair, including soul patch. "I tell him, 'Max, you're Ivy League material. Play the role!'" says Tessa, a nurse who is Max's best friend and style adviser.
After: "He has a sense of pride that was missing before," says Anne. In a perfectly cut pearl gray suit, Max projects the authority he needs for court appearances, yet he doesn't come off as too conservative: There's wit to the mix of striped shirt and polka-dot tie. "Oh my gosh, he looks amazing!" Tessa cries. "I knew he could rock it!"
Suit, Phineas Cole. Shirt, Brioni, $595. Tie, Ermenegildo Zegna, $170. Shoes, John Lobb. On Tessa: Jacket, Madeline Weinrib. Blouse, Kate Spade New York, $195. Jeans, Prvcy Premium, $194. Necklace, Stephen Dweck. Green pyramid ring, Kara by Kara Ross. Ivory ring, House of Lavande. Shoes, Christian Louboutin.