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