Roxana Altamirano, the genius behind Nerd Boyfriend, the blog that offers step-by-step instructions for recreating the ensembles of style icons, offers Details readers tips on how to dress like everyone from Frank Sinatra to Grandmaster Flash.

Woody Allen

Jean-Michel Basquiat

The Beastie Boys

Warren Beatty

Humphrey Bogart

David Bowie

Michael Caine

The Cars

John Cusack, in Bullets Over Broadway

Miles Davis

Robert De Niro in Taxi Driver

Michael Douglas

Clint Eastwood

Harrison Ford

Marvin Gaye

Richard Gere

Grandmaster Flash

Cary Grant in To Catch a Thief

Dustin Hoffman

Buddy Holly

John F. Kennedy

Jack Kerouac

Le Corbusier

Ian McKellen

Dudley Moore in Arthur


Paul Newman

Jack Nicholson in Carnal Knowledge

Ryan O'Neal in Love Story

Tony Perkins

Pablo Picasso

Robert Redford

Rolling Stones

Jake Ryan from Sixteen Candles

Simon & Garfunkel

Frank Sinatra

Christian Slater

James Spader in Pretty in Pink

Bruce Springsteen

Sting in Quadrophenia

Donald Sutherland

Tom Waits

Christopher Walken