The Biggest Celebrity Style Fails and Wins of the Week

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Where: NYC

Need proof that wack shoes can ruin a whole fit? And even though there's nothing wrong with the Canadian Tux, Jay's stain game is too overwhelming.

Where: NYC

Tommy Chong has pretty much been the same dude since his rise to fame with Up in Smoke. Chong kills it here purely by keeping it simple and doing him—plus having a beautiful girl on his arm.

Where: San Juan, Puerto Rico

Sometimes, even if the clothing items aren't bad individually, a poor ensemble can make everything look terrible. Unfortunate candid face aside, the whole poorly-fitting look is a mess.

Where: NYC

Swizzy shows layering up done right, and pulling off the tough task of mixing black and brown. The hat isn't for everyone, but it definitely works here.

Where: L.A.

LMAO. From just a glance, Wayne Brady looks like he's about to play some soft jazz or teach a pick-up artist seminar. Then you notice the lavender trim on his shawl-collar blazer, and realize that Brady was actually trying to be stylish. That LMAO just become a FOH.

Where: Miami

D-Wade has certainly made some, er, "questionable" style choices in the past. But the dude does know how to rock a black suit, and as long as he keeps the pants below capri levels, everything's all good.

Where: L.A.

Homie looks like a caricature cartoon drawing of a Mafioso.

Where: NYC

When in doubt, keep it black and white. Shout out to all the plaids.

Where: L.A.

Too much pink, Rick. Too. Much. Pink.

Where: L.A.

An upscale casual look is always a strong move. Props to the Lord for keeping it cozy without looking too sloppy.