The Kentucky Derby is one of the biggest sports moments of the year. And while we love the performance of the horses and the mint juleps, I have a soft spot for the outfits. I got my start in the menswear world by selling suits. And while most of my clients were there for the suits for their weddings or that of their friends, every year, I got inundated with guys looking to peacock for the Kentucky Derby. It is the one time a year that guys are ready to really let their personalities shine.