The Rocker
Also Known As: The friend of the band.
Dress code: Leather mixed with denim and tailoring. First known sighting: The Sunset Strip, early 1960s. Recent sighting: The VIP area at Bonnaroo. Hall of Famers: Jim Morrison, Lou Reed, Johnny Depp. Signature accessory: Sunglasses. Cause for stress: Receding hairline. Pickup line: "Want to go backstage?" Favorite book: Psychotic Reactions and Carburetor Dung. On his iPod: "Which one? I've got twelve." In his driveway: 1969 Ford Mustang. In his closet: Leather jacket ($2,920) by Dior Homme; cotton-and-linen vest ($498) by John Varvatos; cotton shirt ($165) by John Varvatos Star USA; cotton jeans ($189) by 7 for All Mankind.
The Powerhouse
Also Known As: The master of the universe, the big swinging dick, the man.
Dress code: Power suits, seven-fold ties, black cap-toe oxfords. First known sighting: Drexel Burnham Lambert, 1984. Recent sighting: Testifying before Congress. Hall of Famers: Michael Milken, Gordon Gekko, Jack Donaghy. Signature accessory: Deborah, his longtime personal assistant. Bragging rights: Record profits in 2009. Cause for stress: Barney F--king Frank. Pickup line: "We've got ten minutes until Asia opens." Favorite book: Atlas Shrugged. On his iPod: Radiohead. In his driveway: Cadillac Escalade (with driver). In his closet: Double-breasted wool suit ($7,495), cotton shirt ($595), and silk tie ($215) by Brioni; silk pocket square ($90) by Ermenegildo Zegna; stainless-steel
The Professional
Also Known As: The company man, the shark.
Dress code: Lightweight suits, slim-fit shirts, dark neckties. First known sighting: The Man in the Gray Flannel Suit, 1956. Recent sighting: Up in the Air, 2009. Signature accessory: BlackBerry. Bragging rights: Got a bonus last year. Cause for stress: The size of that bonus. Favorite book: The 48 Laws of Power. On his iPod: Jay-Z. In his driveway: Audi A6. In his closet: One-button wool-silk-and-linen blazer ($1,895), cotton shirt ($395), and wool trousers ($325) by Armani Collezioni; silk tie ($180) by Giorgio Armani; leather shoes ($760) by Church's.
The Italiano
Also Known As: The sprezzatura man, the American who looks vaguely European.
Dress code: Soft-shouldered tailoring, colorful accessories, driving shoes. First known sighting: Naples, Italy, early twentieth century. Recent sighting: Corner table at Cipriani. Signature accessory: Billowing pocket square. Bragging rights: Headed to South Africa for the World Cup. Cause for stress: Not really sure how soccer works. Hobby: Practicing his rolling r's. Pickup line: "Can I buy you a drrrrrrink?" On his iPod: David Bowie. In his driveway: Vespa scooter. In his closet: Two-button cotton blazer ($795) by Prada; cotton shirt ($395) by Ermenegildo Zegna; silk tie ($205) by Ermenegildo Zegna Couture; silk pocket square ($75) by Robert Talbott; cotton-and-linen trousers ($395) by Loro Piana; suede moccasins ($350) by Fratelli Rossetti; leather belt ($275) by Giorgio Armani; titanium Thoroughbred Belmont chronograph ($5,400) by David Yurman; comb by Mason Pearson.
The Rake
Also Known As: The playboy, the ladies' man.
Dress code: Tailored blazers, dress shirts (top three buttons undone), big watches. First known sighting: Las Vegas, 1960s. Recent sighting: The after-after-after party. Hall of Famers: Robert Evans, Joe Namath, Tom Ford. Signature accessory: Chest hair. Bragging rights: Bitchin' apartment. Cause for stress: Psycho ex-girlfriend. Pickup line: "Hello there." Favorite book: The Complete Kama Sutra. On his iPod: MGMT. In his driveway: Jaguar XJ8. In his closet: Two-button mohair-silk-and-cotton jacket ($3,400), cotton shirt ($495), and silk pocket square ($140) by Tom Ford; cotton jeans ($1,450) by Dolce & Gabbana; leather belt ($995) by Brunello Cucinelli; white-gold Big Pilot watch ($26,500) by IWC; bracelets, from left, ($225) by Tod's, ($375) by Luis Morais, ($125) Giles & Brother by Philip Crangi; gold cuff links ($3,650) by David Yurman.
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