Image via Getty Images/Sam Greenwood
Image via Getty Images/Sam Greenwood

Adam Sandler

You know him from: Happy Gilmore, Big Daddy, Grown Ups
Why he shouldn't dress himself: Sandler isn’t going to win any best dressed awards off the links anytime soon either, but the saggy brown shorts and generic sneakers take this ‘fit to new levels of bad.

Image via Getty Images/Michael Buckner
Image via Getty Images/Michael Buckner

Greg Ellis

You know him from: Pirates of the Caribbean series, Star Trek, countless voiceovers
Why he shouldn't dress himself: All sky blue everything. What is this, a Ronnie Fieg “Cove” release?

Image via Getty Images/Hunter Martin
Image via Getty Images/Hunter Martin

Kevin Costner

You know him from: Dances with Wolves, Hatfields & McCoys
Why he shouldn't dress himself: We’re all for classing it up on the course, but the tie? The houndstooth sweater? You stopping somewhere for tea after the game, Kev?

Image via Getty Images/Richard Heathcote
Image via Getty Images/Richard Heathcote

Michael Jordan

You know him from: The G.O.A.T., duh
Why he shouldn't dress himself: His Airness looks like he could fit his entire set of clubs in those ridiculous pants. To be fair, MJ’s golf swag is much more respectable than his street looks, but it’s still not helping his cause. In 2012, Jordan's cargo shorts were deemed so offensive that he was banned from a country club in Miami

Image via Getty Images/Michael Buckner
Image via Getty Images/Michael Buckner

Samuel L. Jackson

You know him from: Pulp Fiction, Star Wars prequels, being one of the baddest SOBs around
Why he shouldn't dress himself: We’re not into overmatching, but Samuel L. was caught looking like he just grabbed whatever he had laying around at this outing.

Image via Getty Images/Frederick M. Brown
Image via Getty Images/Frederick M. Brown

Tim Allen

You know him from: Home Improvement
Why he shouldn't dress himself: When “All Black Everything” goes wrong. If your face looks Photoshopped on, your outfit probably isn’t working.

Image via Getty Images/Al Messerschmidt
Image via Getty Images/Al Messerschmidt

Will Smith

You know him from: Fresh Prince of Bel-Air, Men in Black, Independence Day
Why he shouldn't dress himself: Will looks like he’s dressed for church, not a round on the links. How do you go from a trendsetter to this?

Image via Getty Images/Michael Buckner
Image via Getty Images/Michael Buckner

Anthony Anderson

You know him from: All About the Andersons, numerous supporting roles
Why he shouldn't dress himself: The pink overload is bad enough but c’mon son, did you sleep in those pants too?

Image via Getty Images/Jamie Squire
Image via Getty Images/Jamie Squire

Bill Murray

You know him from: Caddyshack, Ghostbusters, Groundhog Day, Saturday Night Live
Why he shouldn't dress himself: Complete randomness. We can’t hate too much, because Bill Murray is the man, but this outfit looks like something we’d expect to see Gary Busey in.

Image via Getty Images/Gerardo Mora
Image via Getty Images/Gerardo Mora

Chris Kirkpatrick

You know him from: NSYNC
Why he shouldn't dress himself: Wu-Tang Killa Bees meets argyle OD meets WTF?

Image via Getty Images/Stuart Franklin
Image via Getty Images/Stuart Franklin

George Lopez

You know him from: George Lopez show
Why he shouldn't dress himself: How did George Lopez manage to get into all of our grandparents’ closets at once?

Image via Getty Images/J.Sciulli/WireImage for Safilo USA
Image via Getty Images/J.Sciulli/WireImage for Safilo USA

Kevin Nealon

You know him from: Saturday Night Live, Weeds
Why he shouldn't dress himself: We’re sure Kevin Nealon thought he was on trend with this Hawaiian shirt, but instead he looks like he fell in a puddle of mud.

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