Keanu Reeves has played action heroes, time travelers, doofy boyfriends, dashing doctors, and the red-pill–taking savior of the world. He’s also been a red carpet presence since the mid-eighties, donning more than his fair share of boxy suits, dumpy boots, and scraggly haircuts. Journey with us through some of his best — and some of his worst — sartorial moments through the years.
Baby Keanu! This is pre-Parenthood Keanu. Pre-Bill and Ted. This is TV movie–era Keanu.
Photo: Fotos International/2003 Getty ImagesThis is at the Independent Spirit Awards, though you'd be forgiven for thinking it was at the Sloppy Motorcycle Outfits awards.
Photo: Ron GalellaAnd the hunk torch was passed, from Swayze to Reeves....
Photo: Ron Galella, Ltd./1991 Ron Galella, Ltd.Again with the sloppy moto duds.
Photo: Ron GalellaWith Sofia Coppola. Note this early appearance of construction boots. They will come back. A lot.
Photo: Jim SmealSee?
Photo: Jeff Kravitz/e-mail to license FilmMagic images.What is in that bag? Or is that a scarf wrapped around random possessions? Why is he bringing that to a screening of Last of the Mohichans?
Photo: Ro...What is in that bag? Or is that a scarf wrapped around random possessions? Why is he bringing that to a screening of Last of the Mohichans?
Photo: Ron GalellaKinda wish those weren't hiking boots, but otherwise, this feels like a step up.
Photo: Ron GalellaAw, cheer up.
Photo: Ron GalellaThis outfit is presumably from Chicos, home of the flowy-cut linen outfit. (Hi again, construction boots.)
Photo: Ron GalellaSpeed!
Photo: David KeelerOooh, oversized suits from the Chandler Bing collection.
Photo: Ron GalellaHe went through an earthtone-suit phase. It was the '90s. Lots of people did.
Photo: Albert OrtegaNot to be a grumpy dad, but...take that schlubby hat off.
Photo: Ron GalellaYou don't see a lot of people wearing a suit jacket over a leather motorcycle jacket.
Photo: Barry KingThe guy cleans up well, though. (There's a lot going on with that shirt, Jimmy Fallon.)
Photo: Jeff Kravitz/Jeff Kravitz/FilmMagic.comHello, we are perfect human specimens, and we look amazing in formalwear.
Photo: Getty ImagesWhat'd we say about cleaning up nice? See?
Photo: Dan MacMedanProps for adhering to the rule of not buttoning the bottom button.
Photo: Dimitrios Kambouris/Staff PhotographerIt sort of looks like this a weird disembodied prop hand, but fear not. That's Reeves's arm. And tattoo.
Photo: Vera AndersonAnd now we return to the underwhelming footwear. Those are some scuffy boots, friend.
Photo: Amanda Edwards/2003 Getty ImagesUgh, you're a mega attractive super rich movie star! Throw those shoes in the garbage, they are hideous.
Photo: Tony BarsonWhereas this is pretty darn perfect.
Photo: Carlos Alvarez/2005 Getty ImagesA little on the shiny side, but what's life without whimsy.
Photo: Tim WhitbySpeed reunion! God damn those two look cute together.
Photo: Frazer Harrison/2006 Getty ImagesThese boots aren't bad per se, but they don't really go with the (terrific-looking) suit.
Photo: SGranitzAnd they really don't go with this suit.
Photo: Jason MerrittOr this one.
Photo: Junko Kimura/2006 Getty ImagesIt's easy: Formal outfit, formal shoes.
Photo: Stephen Shugerman/2008 Getty ImagesKeanu Reeves, president of the support group for dudes with patchy beards.
Photo: Fotonoticias/2008 FotonoticiasPre-distressed jeans? Never again.
Photo: Ray Tamarra/2008 Ray TamarraGreat head of hair, well-tweezed eyebrows, but man. Patchy beard.
Photo: BARBARA SAX/2009 AFPOooh, rock-star-y.
Photo: Alberto E. Rodriguez/2009 Getty ImagesKeanu Reeves has had a lot of different haircuts. This is among the best.
Photo: Jason Merritt/2010 Getty ImagesThis is not the sad Keanu photo, but it is a sad Keanu photo.
Photo: Frederick M. Brown/2010 Getty ImagesAgain with the dumb boots!
Photo: George Pimentel/2010 George PimentelAnd some different clashing boots...
Photo: Henry S. Dziekan III/2011 Henry S. Dziekan IIIAgain?!
Photo: Sean Gallup/2012 Getty ImagesAh, sweet relief.
Photo: Chris McGrath/2012 Getty Images