For Gary Metzner, the perpetually bow-tied head of office at Sotheby’s, being dapper isn’t just a passion—it’s a job necessity. “In a business like ours, it can be competitive,” says the convivial River North resident, “so I really want to make a point of people remembering who I am.” Mission accomplished: With a preppy, throwback style inspired by ’40s and ’50s icons like Cary Grant and a predilection for colorful accessories like eyeglasses, pocket squares and his beloved green Rolex Hulk (a 50th birthday present from husband Scott), this art lover and frequent charity auctioneer is the master of making a memorably stylish impression.
My earliest style memory is James Bond in his black tie.
If I could turn back time, I would tell myself to wait—the best is yet to come.
The craziest thing I ever did was skydive with my mother.
The first item of clothing I bought for myself was a pair of orange corduroy bell-bottom Levi’s jeans.
My greatest achievement is the money I have raised as a Sotheby’s charity auctioneer.
My favorite places to shop for clothes in the city are Prada and George Greene.
Puerto Vallarta, Mexico, is my idea of perfect happiness.
My fashion splurge is Brunello Cucinelli shoes.
Casual fridays are highly overrated.
Photography by: KEVIN PENCZA ON LOCATION AT 21C MUSEUM HOTEL CHICAGO