Brooke Shields, 2009
Despite her dewy skin and glam tendril, Shields' cobalt blue fascinator (it matches her eyes!) and voluminous lashes are the stand out accents to her Churchill Downs look.
Jessica Simpson, 2004
The then-married Simpson matches her bubble gum lip gloss shade to her pink, large-brimmed hat.
Kim Kardashian, 2009
Between the nude lipstick, contoured makeup, and slinky white dress, it's no surprise that Kim became the mega-watt beauty icon that she is today.
January Jones, 2005
Before Betty Draper, Jones was rocking strawberry-blonde waves and fresh-faced makeup as she attended the Derby with former boyfriend, Josh Groban.
Gabrielle Union, 2008
Union uses highlighter powder to upgrade her already flawless complexion to near-perfection. We love that the brim of her hat doesn't hide her gorgeous mug.
Bethenny Frankel, 2009
The Bravo star ditches her tailored Big Apple look in favor of glossy curls, a seersucker jumpsuit, and a lollipop prop for this Derby Day photo op.
Molly Sims, 2008
While we love big accessories (and bold makeup), for this daytime event, we wish Sims had selected a color palette other than gray for her hat, chunky necklace, and smoky eye look.
Vanessa Minillo, 2010
Minillo's straw hat, straight strands, and poppy pink dress look great against her warm skin tone. We love how her arm candy (and avid Derby fan!), Nick Lachey, matches his tie to her outfit.
Jaime Pressly, 2006
The petite actress knows that bronzed skin is the most striking complement against a black Derby dress and hat.
LeAnn Rimes, 2009
The Mississippi-native opts for soft retro curls as she preps to sing the National Anthem. An advocate of psoriasis patients (she suffers from the chronic condition), Rimes also happily flaunts her picture-perfect arms.