Brooks Brothers has dressed generations of families, prominent and less famous, as well as political leaders, Hollywood legends, sports greats and military heroes.

Cary Grant, Gary Cooper, Douglas Fairbanks, Sr., Rudolph Valentino, Errol Flynn, Rudy Vallee and John Barrymore were some of the best-dressed men of their time, and all were Brooks Brothers customers. Fred Astaire was fond of wearing Brooks Repp neckties as belts. The Duke of Windsor, one of history's most famous dandies, preferred Brooks Brothers dressing gowns. Clark Gable, splendidly proportioned with a 44-inch chest and 32-inch waist, had his suits made to order at Brooks Brothers. He was generally unable to wear ready-made clothing, except for Brooks Brothers button-down Polo collar shirts. Boxer Jack Dempsey's slender feet required fine cordovan leather Peal shoes. Jack Kerouac, the counter-culture icon of the "beat" generation, favored the comfort of Brooks Brothers' button-down Polo collar oxford shirts. Katharine Hepburn, one of the first Hollywood starlets to don trousers, headed to Brooks Brothers for her tailoring. Fran Liebowitz has demonstrated an affinity for Brooks Brothers Shetland sweaters and button-down Polo collar shirts. Designer Todd Oldham favors Brooks Brothers white button-down Polo collar shirts, while Vogue has reported that Brooks Brothers is designer Marc Jacobs' favorite store. Matthew Broderick and Chris O'Donnell are fans and favor classics like Brooks cashmere sweaters. Michael J. Fox, Heather Locklear and the cast of Spin City headed to Brooks' Fifth Avenue store to celebrate their 1999 season premiere. Queen Latifah and 25 other hip hop artists wear Brooks Brothers suits on her new album, The Takeover. Sir Paul McCartney frequently stops by the Fifth Avenue store to do some shopping. Other recent celebrity sightings include James Gandolfini, Jon Voight, Barry Bostwick, Greg Kinnear, Molly Ringwald, Kevin Bacon, and Scott Wolf. Brooks Brothers is frequently sought out by costume designers and worn by celebrities in major films, including Ben Affleck in Pearl Harbor, Gene Hackman in The Royal Tenenbaums, and Will Smith in Ali. Brooks Brothers is the official clothier of the Lincoln Center Jazz Orchestra with artistic director Wynton Marsalis. The orchestra tours the United States wearing Brooks Brothers three-button suits paired with colorful shirts and repp stripe ties.