Every year in the first weekend of May, people from around the world flock to Churchill Downs in Louisville, Kentucky to watch jockeys ride their thoroughbreds for the Kentucky Derby. Of course, this event isn’t just about the racing — it’s also about the fashion.
Women attendees pull out all the stops for the Kentucky Derby. Everyone shows off their inner Southern Belle— and of course, hats are a must. Some people believe that wearing a hat to the Kentucky Derby will bring them good luck. This tradition was started by women, but in recent years, men have been joining in the hat-wearing fun. Read on to see what some of the hottest celebrities in Hollywood have worn to the Kentucky Derby.
Justin Hartley Looks Beautiful In Blue
You probably know Justin Hartley best as Kevin Pearson on the hit NBC show This Is Us. Apparently, when Justin isn’t pretending to be Kevin, he likes to spend his time watching horses run fast around a track.
This photo was taken at the 2017 Kentucky Derby. Justin is wearing a blue blazer with cream-colored pants and a stylish bow tie. Here’s a Kentucky Debry fashion tip: light-colored pants with a darker colored blazer looks put-together without being too matchy. If he had been wearing matching blue pants, this look wouldn’t be as breezy.
First up: a mother and daughter who wore matching outfits in 2009.
Kris Jenner And Kim Kardashian Look Like They Could Be Sisters
Back in 2009, Kris Jenner and her daughter Kim Kardashian attended the 135th Kentucky Derby together. They both chose to wear white dresses. Kris’ dress is a knee length flowy babydoll style dress with black halter straps, and Kim, true to her trademark style, is wearing a form-fitting, body-con dress.
It looks like they’re both wearing the same pair of sunglasses. They’re both carrying black clutches, and they both accessorized with black and white hats.
Laila Ali Looks Stunning In Red
Just last year, in 2018, professional boxer Laila Ali attended the Kentucky Derby in Louisville. She wore a frilly red dress complete with a matching necktie and a stunning black and red fascinator. This dress is lovely, but this look is all about what’s on her head.
We love that Laila chose a shade of lipstick that perfectly matches her outfit. Laila knows a thing or two about what it takes to be successful as an athlete. We wonder if she knows anything about horses…
Read on to see the unconventional suit that Michael Jordan decided to wear to the Derby.
Victoria Justice Chose To Wear All White To The Derby
Former Nickelodeon star and actress Victoria Justice chose to wear all white to the Kentucky Derby in 2018. She’s even painted her nails white to match. Victoria accessorized her outfit with a black hat and a black bag to add some much-needed contrast. She’s also wearing some extravagant statement earrings.
Her hair is down and straight and she’s wearing a bright pinkish red lipstick that’s perfect for the beginning of May.
Michael Jordan Knows How To Rock A Stripe
This photo was actually taken over ten years ago, back in 2007. Former basketball player Michael Jordan arrived at the Kentucky Derby wearing this very Southern-looking beige striped suit. His tie is a darker shade of beige, and it’s checked rather than striped. It’s little details like this that really take this look over the top.
Michael Jordan would look pretty good holding a mint julep in this suit. Actually, the guy standing behind him kind of looks like a mint julep in that green suit.
Gabrielle Union Looks Very 2008 In This Photo
Actress Gabrielle Union showed up to the 2008 Kentucky Derby wearing this stunning ruffled blue dress and a black hat with feather details. This look is quite simple, and very 2008. We think if Gabrielle Union were to attend the Kentucky Derby today, she’d wear something a bit more modern, and possibly a bit more form-fitting.
Gabrielle Union is married to NBA player Dwayne Wade. Dwayne and Gabrielle recently had a daughter, who was born via surrogate in November 2018. Her name is Kaavia James Union Wade.
Keep reading to see what Regina King thought was acceptable to wear back in 2007.
The Whole Food Network Crew Came Dressed To The Nines
In 2017, football player Jerry Rice, Colleen Murray, and Food Network stars Giada De Laurentiis and Guy Fieri all attend the 143rd Kentucky Derby at Churchill Downs in 2017. Giada is clearly the star of this phot when it comes to fashion. That dress is absolutely stunning. There’s even an image of a horses head right in the center of her chest, so its right on theme.
We don’t know about Guy Fieri’s camo blazer, though…
Brooke Shields Came Dressed For The Kentucky Heat
Brooke Shields is an American actress and model. She attended the Kentucky Derby in 2009 wearing this short white sleeveless dress and a blue fascinator with a cage veil. This dress is light and open which means that Brooke didn’t overheat while she was watching the race on a hot spring day.
Brooke looks as gorgeous as ever in this simple and elegant dress. The royal blue fascinator adds a fascinating pop of color.
Regina King Looks Very 2008
Regina King showed up to the 133rd Kentucky Derby looking like literal money. She’s wearing a yellow satin dress with a v-neckline and a wide metallic belt. Her floppy leopard print hat has brown ruffles on it and she’s wearing an elegant gold choker. Her sparkling green earrings add a little something extra to the look.
We don’t know if this is an outfit that Regina would wear in 2019, but it worked for her back in the day.
Keep reading to see which hat Ashton Kutcher chose to wear to the event.
Remember When Jessica Simpson And Nick Lachey Were Together?
Way back in 2004, Jessica Simpson and her husband, Nick Lachey attended the 130th Running of the Kentucky Derby. Jessica wore a giant pink sunhat with matching pink earrings and pink lipstick. Her dress kind of looks like a watercolor painting.
Nick Lachey wore a pinstripe suit with a purple patterned tie and a single stud earring. We don’t think Nick is still sporting that earring in 2019, or at least, we hope he isn’t.
Beyoncé’s Mom, Tina Knowles, Knows How To Dress For A Derby
This is a photo of Robert Lawson and Tina Knowles at the 144th annual Kentucky Derby at Churchill Downs in 2018. Tina really went all out with her antebellum inspired outfit. That black chiffon dress has the perfect amount of drama, and can we talk about that statement necklace? Those have to be real pearls, right?
Tina topped off her look with a black and white spotted fascinator that perfectly ties together her dress and her jewelry.
Zoe Saldana’s Hat Is The Star Of The Show
Zoe Saldana wore this simple white dress and intricate blue hat to the 133rd Kentucky Derby in 2007. Zoe’s dress is very prim and proper, but her powder blue hat is playful and whimsical. Zoe does contrast well. She’s accessorized her look with a simple gold bracelet and some deep red lipstick.
That slit in the front of her dress adds some visual interest while still being modest enough for a Southern event.
Ashton Kutcher Is Too Cool For Kentucky
Ashton’s Kentucky Derby style is enviable, to say the least. First of all, why leave all the hat fun to the ladies? Ashton is out there proving that men should be rocking hats at the Derby too.
Something about the combination of the hat, the vest, the bowtie, the watch, and the sunglasses makes Ashton look like he’s cooler than all of us. This photo was taken back in 2012 at the 138th Kentucky Derby.
Of Course The Queen Dresses Up For The Derby
Queen Elizabeth II doesn’t want to miss out on any of the horse racing action. She attended the 133rd annual Kentucky Derby in 2007 with Prince Philip, Duke of Edinburgh. The Queen has gone for a monochromatic look, as per usual.
She’s wearing a lime green suit with a lime green and bright pink hat. She’s accessorized her look with a gold brooch and two strings of pearls around her neck.
Carson Kresseley’s Shirt And Tie Totally Match
Queer Eye for the Straight Guy original fab five member Carson Kressley attended the 143rd Kentucky Derby in 2017. Carson is wearing a textured blue suit jacket over a blue dress shirt with a multicolored floral pattern on it. He’s also wearing a tie, but it’s hard to spot it because it’s made out of the exact same pattern as his shirt.
The Kentucky Derby is definitely an event you can wear color to.
Read on to see what Kris Jenner and Kim Kardashian were wearing back in 2009.
Miranda Lambert Is The Derby’s Lady In Red
Somehow, Miranda Lambert looks both absolutely adorable and totally edgy in this interesting tea length red dress. This dress consists of a red overlay with circular cutouts over a simple strapless red dress liner.
The outfit wouldn’t be complete without Miranda’s giant red bow fascinator. This photo was taken back in 2014 at the 140th Kentucky Derby. Miranda is sill wearing a sparkly diamond on her left hand because she was still married to Blake Shelton at the time.
Jordin Sparks Looks Like She’s Ready For A Day Of Southern Fun
This is a photo of singer and American Idol winner Jordin Sparks at the 140th Kentucky Derby in 2014. Jordan is wearing a white sleeveless lace dress with a v-neckline. Of course, you can’t go to the Kentucky Derby without a hat, so Jordin is wearing a cream colored hat with a flower detail on the front of it.
Her makeup is natural and effortless and she looks like she’s ready to enjoy a day of fun in the sun.
Kate Upton And Joey Fatone Met Up At The Derby
Kate Upton and Backstreet Boy Joey Fatone must have found each other in the crowd at the 142nd Kentucky Derby in 2016. Here they are chatting together before the race was about to start (or maybe after it ended).
Kate Upton is wearing a gorgeous emerald greed body con dress with cap sleeves and a giant cream colored hat. Joey is wearing a floral patterned suit jacket over a black dress shirt.
Sarah Hyland Knows How To Rock A Fascinator
This photo of Sarah Hyland was taken back in 2015 at the Kentucky Derby in Louisville. Sarah is wearing a white dress with a red floral pattern on it. She’s also wearing a deep red fascinator with a cage veil and some pretty impressive feathers tucked into it.
You probably know Sarah Hyland best as Haley Dunphy on Modern Family. She is now dating Wells from the Bachelor franchise. The two of them are always doing cute things on Instagram.
Nikki Sixx Looks Very Rocker Chic
On May 5th, 2018, Nikki Sixx and his wife Courtney Sixx attended the 144th Annual Kentucky Derby. Of course, Nikki Sixx never wears anything boring. He’s wearing a full red plaid suit over a matching red plaid button down shirt (that he’s left unbuttoned to show off his impressive tattoos).
Courtney is wearing a black and white polka dot dress with a ruffled deep v-neckline. They’re both wearing hats for the occasion.
Titus O’Neil Suited Up
Football-player-turned-pro-wrestler Titus O’Neil looks awfully dapper in this green-checkered jacket that he put on for the 145th Kentucky Derby in 2019. The WWE star wore a blue-striped shirt underneath with khaki slacks. Of course, he completed the look with a multi-colored bow tie.
He may not wear much when he’s in the ring, but best believe that O’Neil knows how to suit up for the occasion, especially one where dressing to impress is key.
Steve Harvey Showing Off With Hats
Hats have traditionally been worn by women to this extravagant event but as we mentioned earlier, men haven’t been afraid to take on the trend as well. Take Steve Harvey, for example. The hilarious game show host showed up to the 2019 Kentucky Derby in a wonderful pink hat that is clearly the statement piece in his entire outfit.
The pink hat does wonders to complement Harvey’s pocket square and pink-striped shirt. We must also give a shout out to that awesome green tie. Yay for color-blocking!
Having Fun With Kevin And David
In Living Color’s David Allen Grier must have taken a cue from Steve Harvey with the pink accents. As you can see, Grier’s pink tie and pocket square are nice pops of color against his grey suit. He too partook in the hat tradition.
Another male who wore a hat to this event? N*SYNC’s own Keven Richardson and his wife Kristin. Keven looks polished to perfection in his fitted blue three-piece suit, while his wife Kristin looks like she’s having tons of fun in a floral pink dress.
Proud Paisley With Joey Fatone
Another N*SYNC member was spotted at the 2019 Kentucky Derby and it was Joey Fatone. You saw him previously on this list completely rocking a floral jacket which is ostensibly why he looks cool and confident in this navy and white paisley number. Continuing the hat tradition, Fatone threw everyone for a loop and wore a navy golf cap to complement his jacket.
He was seen with country singer Travis Tritt, who opted for a more neutral look in a tan jacket and a maroon tie.
Blue Florals For J.D. Shelburne
Country music artist J.D. Shelburne appeared at the 145th Kentucky Derby looking absolutely adorable with is wife. The pair clearly color coordinated their outfits and should be applauded for their execution.
Mr. Shelburne wore a bedazzled grey jacket with blue-floral embroidery and a black lapel. It went perfectly with Mrs. Shelburne’s off-the-shoulder black dress and the blue and black fascinator that makes her look like a perfect Southern belle. They were one of the cutest couples at the 2019 Kentucky Derby.
Wilmer Valderrama Enjoying The Shade
Wilmer Valderrama must have the same sunglasses dealer as Jeff Goldblum and Robert Downey Jr., because don’t those guys also always wear sunglasses like this? Regardless, Valderrama looks awfully suave with his simple Kentucky Derby look.
The glasses serve as a statement and complement the That ’70s Show actor’s rather neutral look. Valerrama went with a tan coat and a floral shirt underneath, which suggests that he wasn’t trying to attract too much attention.
Michelle Williams Flaunts In Floral
Michelle Williams looked absolutely stunning as she pulled up to the 145th Kentucky Derby on May 4, 2019. She wore a floral maxi dress and went for the demure look in all of her poses. Of course, the best part about this singer’s outfit is her incredible hat. The pale pink number was embellished by a by and blue and white feathers.
The former Destiny’s Child member clearly came to slay at this event.
Father And Daughter Looking Pretty In Pink
Anna Nicole Smith’s daughter Dannielynn is so grown up now! She attended the 145th Kentucky Derby with her father, Larry Birkhead. Dannielynn looks absolutely adorable in her pink ruffled dress, complete with pearl accessories and a huge pink hat to match.
Dad made the right move by coordinating his outfit with his daughter. Birkhead dressed up in a simple pink suit with a patterned tie. This father-daughter duo ought to have had a truly unforgettable presence at the races.
Avery Williamson Snapped A Selfie
New York Jets linebacker Avery Williamson was spotted snapping a selfie as he pulled up to the 145th Kentucky Derby at Churchill Downs in 2019. And why wouldn’t he? Williamson looks awfully spiffy in his selected Derby outfit.
The football player wore a dotted black shirt and went with an eye-popping pink paisley tie. It’s a good thing that he found a pocket square to match! It all looks perfect wrapped up in his grey suit jacket.
A Look From A Different Era
If you don’t recognize this man by face then you might if you were able to hear what he was saying in this photo. Patrick Warburton has lent his voice to many films and television shows, but he most recently made a killing as Lemony Snicket on Netflix’s A Series of Unfortunate Events.
Warburton is being interviewed in this photo and is likely talking about his dapper striped suit. He ought to have come out of a different era with a suit like this! It goes perfectly with his striped bowtie and fedora hat.
Truly The Most Eye-Catching Outfit
They may not be celebrities in the U.S. – yet – but this outfit deserves a mention. Daniel Lismore is cited by Vogue Magazine as “England’s Most Eccentric Dresser” and it’s clear to see why.
The British fashion designer came to the 145th Kentucky Derby in an industrial-inspired look, complete with a complementary crown. With giant safety pins, jewels, gems, and more, Lismore clearly came to grab attention. He attended with hotelier Steve Wilson, who opted with a more simple look in a red jacket and patterned suit.
Bonnie-Jill Looks Absolutely Thrilled
When she’s not reporting from the court, Bonnie-Jill Laflin is hamming it up on the red carpet. Here she is arriving at the 145th Kentucky Derby looking absolutely darling in a black, white, red, and gold ensemble.
The NBC Sports Bay Area sportscaster wore a floral dress with a halter top but it’s her hat that is clearly the showstopper. With a white base, the hat has red roses and colorful feathers to make it a true sight for the eyes.
Staying True To Those Country Roots
Country music singer Tracy Lawrence wouldn’t let people forget what he’s known for when he wore this western-style chapeau to the 145th Kentucky Derby. The “Sticks and Stones” singer looked mighty suave in his cowboy hat, which he complemented with a navy and black pinstripe suit.
There was nothing to distract the eye when it came to this outfit, since Lawrence also wore a black shirt underneath. While everyone opted for eye-catching accessories and colors, Lawrence decided to keep things simple and low-key.
Star Jones Brought Her Trusted Companions
Star Jones looks stunning in her black and white dress! The former The View co-host wore a flowing high-low gown with ruffles at the end and lovely heeled sandals to match. Of course, what really makes her outfit extravagant is the black, feathered hat that she wore in true Kentucky Derby fashion.
She brought with her two forms of eye candy: her lovely little pooch and her husband Rucardo Lugo. Here’s one couple that didn’t color coordinate but it actually works for them! Lugo looks dapper in his purple jacket and fedora, helping him and his lady stand out.
Jennifer Nettles Is Stunning In Ruffles
Sugarland lead singer Jennifer Nettles had one of the most magical dresses on the Kentucky Derby red carpet in 2019. Her lavender tulle dress had plenty of ruffles, adding texture to the look and drawing the eye both to her feet and her head. She even has lavender gloves!
What’s interesting about this look is that she decided to complement the lavender with baby pink accents. The singer-songwriter wore pink heels and an amazing pink fascinator.
Lovely Yellow Vibes From Nene
Nene Leakes attended the 145th Kentucky Derby looking bright in a svelte yellow number. Yellow is a color that is supposed to evoke happiness, so it’s no surprise that Leakes is all smiles while attending this 2019 event!
Her yellow dress was complemented with some silver pointed-tow pumps but what we really love is the floral headpiece that Leakes wore! The orange tones of the flowers mesh perfectly with her bright dress.
Red Polka-Dots For Natalie Zea
Passions actress Natalie Zea wore this incredible off-the-shoulder dress with long sleeves. The red-polka-dot pattern doesn’t look over the top considering the ruffles on this mini dress. It all comes together to complement Zea’s svelte figure quite nicely.
The actress pulled off this look perfectly with red pumps and a neat, red fascinator. Honestly, the Justified actress had one of the best Kentucky Derby looks of 2019, mixing traditional style with modern flair.
Taylor Dane’s Day At The Races
Remember Taylor Dane? The “Tell It to My Heart” singer reemerged that the 145th Kentucky Derby looking incredible in her simple but sophisticated outfit. Dane wore a navy blue jumpsuit with a halter top and cut-out in the front. The top has a ruffled neck with yellow accents.
Dane also wore a hat to the races but opted for this floppy, white sun hat that makes her look like a reinvented Southern belle.
Cynthia Bailey On The Prowl
Nene Leakes wasn’t Atlanta’s only Real Housewife to make an appearance at the 2019 Kentucky Derby! Cynthia Bailey attended with her dashing beau, Mike Hill. Hill wore a cream-colored pinstripe suit and added a hint of color with his blue, floral tie.
But clearly, the real stunner in this couple is Bailey herself. She wore a cheetah print dress with a plunging neckline, adding a bit of fierceness to this event. Her fascinator is one to be remembered as well, with its striking shapes.
Jordan Smith And Wife Contend For Best-Dressed Couple
Jordan Smith, winner of season nine of The Voice, attended the 145th Kentucky Derby with his wife Kristen. The lovely couple looked amazing in their color-coordinated outfits. For his part, Jordan wore a blue suit jacket with shiny, blue statement loafers.
He was clearly dressed to complement Kristen’s adorable outfit! She wore a pink and blue floral dress with blue heels. It was the perfect shoe choice since it didn’t distract from her fun blue and pink fascinator!