Hot and Covered...THE WELL-DRESSED REBEL

Short-Change Yourself

Michael Macko, Director of Menswear, Saks Fifth Avenue

“When you wear a blazer with shorts, you get the feeling that you’re dressed up, but you’re still casual. It says, ‘I don’t work for The Man.’ Most guys, if they’re going to pull this look off, would probably be more comfortable wearing an unstructured cotton jacket with busted-up cargo shorts. It takes a brave man to wear a tailored jacket with tailored shorts. But that’s the point: It’s something you’re not supposed to wear. That’s rebellion.”

• Whether you wear a crisp blazer or a rumpled cotton sports jacket, skip the socks. As Macko says, you don’t want to look like you live in Bermuda.

Blazer by Ralph Lauren Black Label. Shirt and tie by Charvet. Shorts by Michael Bastian. Shoes by Church’s.

Photo: Ben Watts

Show Some Ankle

Andy Spade, Founder, Jack Spade

“Going sockless started when I was growing up in Arizona. It wasn’t a style choice—we just never wore socks unless we were playing sports. Now I wear a very slight break in my pants, so they just touch the tops of my shoes. When I’m standing up, I don’t want to have my ankles exposed; it’s when I sit down that you see the sockless thing. People ask me if I go through shoes fast, but I take care of my shoes and keep shoe trees in them. And it’s not like I play tennis without socks. But desert boots, brogues, or Wallabees—it’s the way I’ve always worn ’em.”

• Want to go sockless but not all the way? Go to www.bananarepublic.com and buy some all-but-invisible “loafer socks.”

Sports jacket by Thom Browne New York. Shirt by Brooks Brothers. Jeans by Levi’s. Boots by Clarks.

Photo: Ben Watts

Beat Up the Pretty Things

Nathaniel Goldberg, Photographer 

“There’s a person at the Serpette flea market in Paris who specializes in secondhand Herm?s bags. I bought these about ten years ago; they’re probably from the late ’60s or early ’70s. I paid about $2,000 apiece, but I take both of them with me everywhere, always as carry-on luggage. One I pack with clothes, the other with shoes, toiletries, and a computer. You travel in style, but you pay for it with how heavy they get. It’s a painstaking experience, but I still do it. You have beautiful bags; you want them with you.”

• The fact is, quality will cost you. But if you invest in a classic piece by a label like Herm?s—whose craftsmanship is undisputed—consider it money well spent.

Bags by Hermes. Vest and shirt by 45rpm. Jeans by A.P.C. Cap by Browning. Glasses by Number (N)ine. Watch by IWC.

Photo: Ben Watts

Sock It to ’Em

Paul Smith, Designer

“My clothes have always been described as classic with a twist. And the twist comes from self-expression—you’re still well-mannered, you’re a good businessman, you wear a smart suit, but you want to wear one wacky thing, like a pair of socks. And that’s how I got started; I didn’t want to stick out like a sore thumb, but I still wanted to be a bit tongue in cheek. In fact, yesterday I wore lime green socks, dark blue jeans, a pin-striped navy suit jacket, and black lace-ups. You see—I’m still doing it!”

• When buying vibrant dress socks, consider the rest of your wardrobe. Lots of soft-blue shirts and navy ties? Look for socks with at least some blue in them, no matter the shade.

Socks by Paul Smith Accessories. Pants and shoes by Paul Smith.

Photo: Ben Watts