This is a guest style post by Emily Sandford – Gwynnie Bee member, blogger at Authentically Emmie, and Kentuckian. 

Most days of the year, I can tell someone I’m from Kentucky and they yawn. Once Derby draws near, however, everything changes!

Derby style with #gwynniebee Left: Dress coming soon to Gwynnie Bee
Right: Lands’ End Sleeveless Lace Column Dress, sizes 10-26

The Kentucky Derby always takes place at Churchill Downs in Louisville on the first Saturday of May. This year marks the 140th Run for the Roses (aptly nicknamed as a blanket of roses is draped over the winner.) For locals, the first Friday in May is also of huge significance as it’s the running of the Kentucky Oaks: a Grade I Stakes race of the best 3 year old fillies (lady horses) in the country. You’ll see the same signature Kentucky horse racing style among patrons, but probably fewer celebrities.

#gwynniebee is ready for the #kyderby
BB Dakota Micah Dress
, sizes 14-24

For Derby, there aren’t necessarily fashion rules, but there are some things you’ll notice:

  • Prints over sparkle: The daytime event means less dresses covered in sequins and more with vibrant prints: florals, chevron, polka dots, and more. It also means more short lengths than maxis. And no jeans, unless you’re in the infield.
  • Heels: Many women wear heels, but wedges or flats might be better suited for several hours of standing and sipping on mint juleps.
  • Accessories: Depending on the size of your hat, you may or may not want to remember to bring sunglasses. You might see liberally worn jewelry depending on the level of adornment on the hat.
  • Man style: Be prepared for men decked out in seersucker, plaids, and prints, as well as light shaded suits with colorful pocket squares.
  • Hats: If you want a hat to be remembered by, you should contact a milliner several months in advance and plan to spend anywhere from $400-2000. Many people choose to make their own hats, adoring them with feathers, moldable mesh, silk flowers, tulle, ribbons, and the occasional horse figurine or Barbie doll. Many Derby patrons believe that “more is more” when it comes to hats.

#gwynniebee is ready for the #kyderby
Lands’ End Keyhole Dress in Pink Lemonade, sizes M-3X

Fun facts about the Kentucky Derby:

  • This year, jockey Rosie Napravnik is hoping to make history as the first female jockey to win the Kentucky Derby. Her mount this year is Vicar’s in Trouble, currently a 20-1 long shot.
  • Want to see Derby celeb style in person? The Kentucky Derby Museum at Churchill Downs has a display of some of the most famous Derby ensembles – hats included. A personal favorite? Anna Nicole Smith’s over-the-top pink ensemble with tulle-covered hat.
  • If you want to do some celebrity gazing, the best place is likely NOT the Derby, but the parties that lead up to the first Saturday in May. There are oodles all over Louisville, including the most talked-about Barnstable Brown party. Among this year’s guests: Kings of Leon, Miranda Lambert, Gene Simmons, Tom Brady, Salt-n-Pepa, and more.

Are you planning a stylish Derby day?

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