Be a Man—Wear Jewelry
Philip Crangi, Jewelry Designer
“People tend to think of jewelry for men in extremes, and it doesn’t function well at extremes. It’s not about chunky silver or NBA diamonds. What it comes back to is, Does it look personal? It should look like you’ve been wearing it for years—something you picked up along the way. I don’t want to look flashy. I want to feel comfortable. When you’re buying jewelry, all you need to ask is, ‘Do I feel like myself with it on?’ ”
• Want to get into jewelry? Start with a wrist piece and add to it over time, with a necklace and a ring or two. Don’t run out and buy a Mr. T–worthy haul all at once.
Necklaces by Philip Crangi. Bracelets by Giles & Brother by Philip Crangi. Watch by Hermès. T-shirt by American Apparel. Glasses by Moscot.
Tame Your Tux
Dao-Yi Chow, Designer, Public School
“If you look at my outfit, it’s formal from the waist up and nontraditional from the waist down. It’s the perfect balance between luxe and edge. There’s still a fashion component to it, but the way you put it together, you’re not fashion. To pull it off, you have to pay attention: You have to keep the lines from the jacket to the jeans—and the jeans to the shoes—in proportion.”
• The reason Dao-Yi’s outfit works so well is he pays as much attention to the fit of his jeans as he does to his tailored tux jacket. They’re perfectly in sync with each other.
Tuxedo jacket and jeans by Alexander McQueen. Shirt by Dolce & Gabbana. Bow tie by Polo by Ralph Lauren. Sneakers by Balenciaga.
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.
Stick Your Next Out
Dexter Peart, Designer, WANT Les Essentiels de la Vie
“Wearing a collar pin is elegant and a little old-school: Steve McQueen in The Thomas Crown Affair mixed with Remington Steele. I don’t necessarily buy shirts that have collar-pin holes in them—I’ve just been putting holes in my shirts as I go. And I’m wearing pins with every kind of collar: spread, club, and regular. And I have two watches: a silver Cartier with a brown band, and a gold Cartier with a black band. So when I wear the gold watch, I wear the gold collar pin; when I wear the silver watch, I wear the silver collar pin. It depends how I’m feeling that day.”
• Think of a collar pin as you would a tie bar: another accessory that’s back in style. Use it to strike an old-world note in an otherwise modern outfit. The object is to not look like you’re wearing a head-to-toe costume.
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.
Beat Up the Pretty Things
Nathaniel Goldberg, Photographer
“There’s a person at the Serpette flea market in Paris who specializes in secondhand Hermès 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 Hermès—whose craftsmanship is undisputed—consider it money well spent.
Bags by Hermès. Vest and shirt by 45rpm. Jeans by A.P.C. Cap by Browning. Glasses by Number (N)ine. Watch by IWC.
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.
Wear a Suit—Don't Look Like One
Luigi Martini, General Manager, Kiton in N.Y.C.
“I grew up between Santo Domingo, the United States, and Italy. I call my style ‘shock by shock.’ It’s one thing after another, and the only word you can come up with is Wow! In school, when I was little, I was supposed to wear my tie perfect every day. When I left school, I realized that I didn’t have to please anybody anymore. I started tying my tie with the narrow end longer, and everybody asked me if they could wear my style. That made me happy. I don’t believe that you have to get up every morning and look for a belt that matches your shoes. Life is short.”
• Luigi’s look is enthusiastic, not ironic. He’s wearing an expertly tailored Italian suit and a beautiful shirt and tie. The precision of these pieces allows him to step out a bit—okay, a lot.
Suit, shirt, tie, pocket square, and belt by Kiton. Sneakers by Superga. Watch by Rolex. Bracelets (on left hand) by Dodo.
Wear It on Your Chest
Derrick Miller, Creative Director, Barker Black Ltd.
“My dad always said the one part of your outfit you should have fun with is your pocket square. This lime green one was in Barker Black’s very first collection, and I pretty much wear it every day. It’s a little outside my comfort zone in terms of how bright it is, but I like how it pushes the envelope. I have a lot of gray and navy in my wardrobe, and it pops against those colors. My brother and I go back and forth about how to fold a pocket square. My dad just jams it in there, over and over—it’s like a Jackson Pollock. It looks crazy when he’s doing it, but then all of a sudden it’s right. Sometimes it’ll hang four or five inches out of his pocket. I’m not quite there yet; I like to think I’m still a bit more reserved than that.”
• Your pocket square should complement your tie, not match it exactly: You don’t want to look like Jimmy and Howie on the Fox NFL pregame show.
Pocket square, tie, and shoes by Barker Black. Suit jacket by Thom Browne New York. Shirt, custom-made. Pants by Paul Stuart.
Live It Up—Dress Down
Walker MacWilliam, Vice President, Men’s Design, Coach
“I don’t like fake distressed clothing; I like it to be my distressed. There’s nothing better than when clothes age: Jeans fit you better, chinos break down and soften. But it’s also how you age them. I’ve never owned an iron; I have zero dry-cleaning bills. I wash all my shirts and hang-dry everything. That’s my recipe for perfectly wrinkled clothes. Because there’s good wrinkled and bad wrinkled. I know good wrinkled and what fabrics are going to give it to me. I don’t want to look like I slept in my clothes.”
• The key to Walker’s aesthetic is no matter how beat-up and worn-in his clothes get, they’re still American classics: oxford-cloth shirts, chinos, canvas sneakers, a leather bomber.
Jacket, vintage. Shirt by Ralph Lauren Black Label. Tie by Prada. Tie bar by Hermès. Khakis by RRL. Sneakers by Converse by John Varvatos. Glasses by Paul Smith Spectacles.
Lose the Links
Wayne Maser, Photographer
“I wear Charvet French-cuff shirts all the time. But I travel a lot, and I kept losing my cuff links—they would just disappear. A couple of years ago, I was in a rush, and all I could find were these garbage ties. Now I go into bakeries all over the place, looking for the gold or silver ones they use. I’ve stopped buying cuff links entirely; I only use bakery ties—that’s what I like to call them. When you’re in a pinch, they’re a great emergency aid. Not good, great.”
• If you’re going to go for Wayne’s trick, just remember: Do it with confidence. You will get comments.
Shirt and pocket square by Charvet. Sports jacket by Richard Anderson, London. Glasses by Oliver Peoples.