Celebrities In Wild Hats At Kentucky Derby: Dannielynn Birkhead & More

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May 6, 2023 12:00PM EDT

Ahead of this year’s Kentucky Derby, look back at some of the wild hats that stars have worn to the event over the years!

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Celebrity Hats At Kentucky Derby: Photos

Celebrity Hats At Kentucky Derby: Photos — Hold your horses! The Kentucky Derby is back! Called ‘the greatest two-minutes in sports’, the horse race takes place each year in Louisville, Kentucky. It is almost always on the first Saturday in May, which caps the two-week-long Kentucky Derby Festival. (In case you didn’t know, the festival is only Kentucky’s largest single annual event, which was founded all the way back in 1935.) The competition itself is a stakes race for three-year-old Thoroughbreds and it is held at Churchill Downs.

The Derby isn’t just a race, but also one of the most fashionable celebrations of the South. People go all out with their looks, which almost always feature the addition of a fabulous hat. Whether people top their looks off with hats, fascinators, or dainty veils, the chic headwear is both traditional and fashionable.

Our favorite celebs know just how to rock a fabulous Kentuc ky Derby Hat. Check out the very best looks chosen by our HollywoodLife fashion experts with photos of Michelle Williams, NeNe Leakes, Katie Couric and more here.

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Dannielynn Birkhead & Dad Larry Birkhead In 2022

Dannielynn Birkhead & Dad Larry Birkhead In 2022 — Anna Nicole Smith’s daughter, DannieLynn Birkhead, looked all grown up while attending the Kentucky Derby in 2022 with dad Larry. She wore a colorful dress and bright blue fascinator hat.

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Elle Smith

Elle Smith — Elle Smith flashed a big smile while at the 2022 Kentucky Derby. She wore a pink outfit and wore a bright pink floral headpiece to match her dress.

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Jason & Brittany Aldean

Jason & Brittany Aldean — Jason Aldean and Brittany Aldean had a date night while attending the 2022 Kentucky Derby. Brittany added a pop of color to her white outfit with a purple hat.

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Megyn Kelly

Megyn Kelly — On May 7, 2016, Megyn Kelly looks elegant in her spaghetti strap dress and white derby hat. The hat covered half her face for a dramatic look.

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Michelle Williams

Michelle Williams — Michelle Williams wore a floral dress and light pink hat while attending the Kentucky Derby. She paried the look with open-toed heels and a clutch.

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Katie Couric

Katie Couric — Katie Couric looks pretty in pink in 2017. The journalist donned a bright pink floral dress and hat at the May 6 derby.

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Tammy York & Tonya York

Tammy York & Tonya York — Tammy York & Tonya York appeared together. The duo stunned in pretty colors at the 145th Kentucky Derby, Arrivals, on 04 May, 2019.

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Joey Fatone

Joey Fatone — Joey Fatone looked dapper in a navy blue paperboy hat at the 145th Kentucky Derby on May 4, 2019. His patterned suit was also quite snazzy.

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Star Jones

Star Jones — Star Jones and her adorable pup matched on the red carpet at the 145th Kentucky Derby on May 4, 2019. She wore an elaborate black hat, and her doggo donned a matching black bow. So cute!

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Cynthia Bailey

Cynthia Bailey — Real Housewives favorite Cynthia Bailey looked so classy at the 145th Kentucky Derby on 04 May 2019. The reality star wore an animal print dress with an incredible headpiece!

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Tricia Barstable Brown

Tricia Barstable Brown — Tricia Barstable Brown was a vision in purple at the 145th Kentucky Derby, on May 4, 2019. Grey really is her color!

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Bozoma Saint John

Bozoma Saint John — Princess perfect! Bozoma Saint John rocked a feathered purple gown with a matching headpiece at the 2019 Kentucky Derby.

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Phaedra Parks

Phaedra Parks — Fashion forward! ‘RHOA’ star Phaedra Parks was a vision in a one-sleeved dress which she paired with a super unique, pink headpiece at the 2019 Kentucky Derby.

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Dylan Dreyer

Dylan Dreyer — Flower power! Dylan Dreyer stunned at the 2019 Kentucky Derby in a pastel floral dress, and an orange fascinator that featured a huge flower!

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Von Miller

Von Miller — How dapper. Von Miller rocked the red carpet at the 2019 Kentucky Derby in a light purple suit and matching fedora with a red rose.

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