The Kentucky Derby takes place tomorrow, so we've decided to look at the style made popular by jockeys and horseback riders. We've cracked jokes on this look before (sorry, we're not sorry Chris), but that hasn't stopped celebrities from rocking the equestrian look on some normal-day steez. It's kind of like when dudes try the nautical trend, but go full on sailor head-to-toe. Yeah sure, we all want to ride dirty with a thoroughbred, but are these guys taking it too literallly? We've rounded them all up from the highs and lows, wins and losses of this trend for your viewing pleasure and possibly your laugh of the day. Check out our gallery of Celebrities Wearing Equestrian Gear.