A long-haired, youthful George Clooney attended a celebrity basketball game in 1989 wearing a leather vest, jeans, and a printed shirt.
With his hair still long and wavy, the actor ditched his denim-and-vest ensemble for a navy suit and printed tie to attend a party in 1989.
Leaving the airport in Los Angeles in 1995, Clooney looked simple and chic in navy chinos, a white t-shirt, and round sunglasses.
Attending the 52nd annual Golden Globes in 1995, Clooney looked like a classic heartthrob in a classic suit and bow-tie.
Ditching the long hair he is seen here at the 48th Emmy Awards in 1996 wearing a classic tux and with his now well-known salt and peppery hair.
At the premiere of “The Peacemaker” in 1997, Clooney chose a more casual look on the red carpet, leaving the collar of his shirt unbuttoned.
George Clooney and his girlfriend Celine Balitran hit the red carpet in 1998. The actor took a fashion risk, wearing a maroon-colored suit.
Clooney dressed for the occasion at GQ's Men of the Year award ceremony in 1998.
Off the red carpet, Clooney wore a denim-on-denim outfit.
Clooney took home a Golden Globe award at the 58th Annual Golden Globes wearing a classic tux.
Attending Venice Film Festival in 2005, Clooney wore a classic suit while on a boat with the actress Patricia Clarkson.
Posing with longtime friend Brad Pitt in 2008 at the press event for “Burn after Reading,” Clooney wore a classic, Italian-style suit.
Stepping out after an appearance on "The Late Show with David Letterman," Clooney looked sophisticated in a navy, pinstripe suit.
Clooney kept it classic at the 69th Golden Globes in 2012, where he took home the award for best actor.
George Clooney wore a perfectly tailored grey suit and sunglasses to celebrate his marriage to Amal Clooney in Venice.
Amal and George Clooney cemented their status as one of Hollywood's most stylish couples while attending the Met Gala in 2015.
George and Amal Clooney landed on all the best dressed lists at the 72nd annual Golden Globes in 2015 with their homage to Hollywood glam.
Always ahead of the trends, Clooney wore colored sunglasses with a well-fitting suit to the Cannes Film Festival in 2016.
Clooney shared a moment with his longtime friend, the actress Julia Roberts, on the red carpet at the Cannes Film Festival in 2016. Both wore elegant, classic ensembles for the occasion.
Wearing a turtleneck instead of a traditional collared shirt, Clooney makes a case for casual red carpet style while attending the “Hail Cesar” premiere in 2016.
George Clooney looked both comfortable and sophisticated wearing a knitted scarf and suede jacket while walking around Paris with his wife Amal in 2017.
Actor George Clooney kept it classic in a tuxedo at an Omega Event in 2017.