Whether you like relaxed fit and full coverage or cut off, we tapped style experts to pick their favorite men’s shorts.

Most of the best Kentucky Derby outfits for men have had their roots in preppy style. A single or double-breasted navy suit or sports jacket paired with a light-colored shirt is a smart choice.

Our "Let's Talk Derby with Kathryn & Kirby" video series explore the different types of hats men can wear to the Kentucky ...