- Attendees always show up to the Kentucky Derby in head-turning hats and fascinators, as is tradition.
- Celebrities like Kim Kardashian West and Kate Upton have worn eye-catching designs in the past.
- The 2020 Kentucky Derby was originally set to take place on May 1 but has been rescheduled to September 4.
- Visit Insider’s homepage for more stories.
Each spring, the Kentucky Derby attracts hundreds of thousands of people to Louisville’s Churchill Downs. And while 20 fierce horses running the track at top speeds is the ultimate adrenaline rush, it’s the fashion that truly makes this race a spectacle.
This year, the annual horse race was rescheduled for the first time since 1875. It was meant to take place on May 1 but has been rescheduled to September 4, 2020.
In the past, everyone from celebrities like Kim Kardashian West and members of the royal family to first-time attendees have geared up in their best hats and spring ensembles. Sporting a headpiece at the event is believed to bring good luck, according to the Kentucky Derby website. And though the tradition was started by women, men have also started wearing more unique hats in recent years.
Insider rounded up the wildest Derby hats that would give even the British royal family a run for their money.
This showstopping white feather hat was spotted on a Kentucky Derby fan in 2004.
The costume piece jazzed up the racing fan’s white retro sunglasses.
Jessica Simpson also attended the 2004 race in a candy pink hat.
The singer and actress looked beach-ready in her oversized accessory.
Two fans tapped into the race’s history by wearing rose hats at the 2005 event.
Red roses spilled over the sides of the hat on the left, while they were subtly incorporated to the black cowboy hat on the right.
Another 2005 racegoer honoured the Kentucky Derby’s official flower.
Black sunglasses and red lipstick served as the ultimate accessories to the festive hat.
Fake money, horse figurines, and other knickknacks were piled onto a 2006 hat that appears to be the result of some serious DIY skills.
It nearly sums up the race.
Fruit, wine, and rose details enhance this neon pink felt top hat from the 2006 event.
Surrounding the embellishments was a thick layer of fuzzy white trim.
This baby pink sun hat was a sweet option for the 2007 Kentucky Derby.
The woman’s accessory complemented the light pink polka dots visible on her top.
Queen Elizabeth II graced the 2007 Kentucky Derby with her presence in a lovely mint ensemble.
Vibrant watermelon pink fabric wrapped around the top, securing a perfectly knotted bow.
This pure white hat, spotted in 2008, had a strikingly chic silhouette.
Three small feathers were fastened to the side.
Actress Tischina Arnold selected a structured design to wear to the event in 2008.
She accessorized with drop pearl earrings.
Leave it to Kim Kardashian to channel old Hollywood glamour with her 2009 Kentucky Derby hat.
She also wore her signature oversized sunglasses.
Actress and producer Lynn Whitfield pulled off a daring blue feathery piece in 2008.
She looked luminous against the bright aquamarine tones.
Sheer checkered fabric is a staple for summer, as demonstrated by a 2010 Kentucky Derby spectator.
While understated and classic, the transparent fabric over the white hat nearly creates an optical illusion of complex dimension.
Ashlee Simpson’s cloche hat stood out among the larger elaborate headpieces at the 2010 races.
Simpson completed the look with a red and white polka dot dress.
Layers of sheer black fabric were fashioned into a billowing bow for this 2011 race look.
An understated colour scheme of black and white completed the rest of her outfit.
A 2011 attendee kept the sun off her skin in a massive coppery hat.
A thick gold ribbon served as a clean accent.
An abundance of feathers draped over the brim of Kate Gosselin’s wild hat in 2011.
Tan tulle accented the top of her hat.
Here, an eye-catching splash of blue was captured at the 2012 event.
Feathers and tulle livened up the striped white sun hat.
Pink flowers and a dense pile of peacock feathers adorned this 2012 headpiece.
This guest also fastened a matching pink flower to the sleeve of her shirt.
This 2012 hat looks like it came straight out of a fashion editorial.
A spring look at its finest.
Embedded within this leafy green top hat from 2013 was an abundance of red roses and miniature horse figurines.
A traditional black brim was visible beneath the baffling tower.
Supermodel Coco Rocha served a look when she wore an orchid-inspired hat for the 2013 Kentucky Derby.
She even pulled off a lavender lip.
Krysten Ritter wore a regal creme headpiece at the 2013 Kentucky Derby.
Robin’s egg blue fabric bordered the brim and tied into an large bow at the back.
Feathers sprawled across actress Star Jones’ 2013 Kentucky Derby hat.
Jones’ accessory looked like it was almost floating over her head.
Tiny hats have their place at the races too, like this 2014 example.
This racegoer paired her colourful hat with equally festive glasses.
Horse-racing champ Tami Purcell wore this hat in 2014.
Though covered in springy flowers, the headpiece looked like it was inspired by autumn.
A devoted race fan from 2014 donned a white top hat depicting the venue in action.
Signature red roses dotted the underside of the brim.
Like many Kentucky Derby goers, Johnny Weir opted to wear an elaborate hat featuring a horse-like figurine for his 2014 appearance.
On his website, Weir explained that his original hat, designed in collaboration with Kerin Rose Gold, was titled “Pegasus” for the mythical figurine featured on his accessory.
Rapper Cheryl James, better known as Salt, took a style cue from Hello Kitty when she wore a large pink bow for the 2014 Kentucky Derby.
By sweeping her hair back into a sleek, sophisticated updo, James put all focus on the headpiece.
Model Lindsay Ellingson attended the 2015 Derby wearing a burgundy fascinator.
Ellingson paired her pretty accessory with a white spring dress.
One 2015 Derby fan was a vision in a unique hat that featured a flamingo sitting inside a basket.
Ironically, the flamingo’s floral straw hat was more in line with the headpieces traditionally worn to the Kentucky Derby.
Sarah Hyland embraced florals and feathers at the 2015 race.
Two long feathers and delicate netting transformed the crimson accessory into a standout piece.
A woman at the 2015 race wore a sheer white hat that covered most of her face.
The hat featured a cream centre flower and a display of feathers.
This woman took the racing theme quite literally in 2015.
Each colour marked a different prize, such as “fourth place,” “third place,” and “second place.”
Kira Kazantsev, Miss America 2015, rocked a fascinator with cherry red plumage at the 141st Kentucky Derby.
She sealed the look with classic red lipstick to match.
Blue and pink made for a whimsical choice at the 2015 Kentucky Derby.
Layered pearl necklaces completed this racegoer’s Southern Belle look.
Robin Meade’s 2015 white fascinator hat resembled a crown.
She secured the accessory far back on her head.
A sleek horse was the focal point of this hat from 2015.
The white hat had a classic silhouette with a thin black stripe.
A cocktail was casually buried within the blanket of red roses covering Johnny Weir’s 2015 Derby hat.
Weir posed next to Tara Lipinski whose blonde hair was styled into intricate braids.
At the 2016 Kentucky Derby, Clark Davis (Miss Kentucky 2015) paired her sash with an exquisite hat.
Flowers stretched out of the accessory’s artistic centrepiece.
This voluminous red hat gracefully draped over a woman’s face at the 2016 Kentucky Derby.
She wore a monochromatic look with red lipstick and a red dress.
Flower hats were interpreted differently among the most spirited race attendees, such as this example from the 2016 event.
The arrangement orbited around a centrepiece of traditional pink flowers.
Roses are a popular hat embellishment from year to year, but one woman took the flower to the extreme in 2016.
The sculpted petals were a classic shade of red.
Figure skater Tara Lipinski ditched flowers and pastels for a fierce lacy fascinator in 2016.
The former Olympian’s semi-sheer white dress had mesh paneling and splashes of red throughout.
Actress Cassandra Jean was one of the few to stray from pastel spring colours with her 2016 Kentucky Derby hat.
Smooth flowers in the same shade of purple seamlessly blended with the fabric of her headwear.
Actress Rachel McCord’s inverse hat was a unique take for the 2016 race.
Clustered in the centre of the beige hat was an arrangement of tiny pearls.
Model Kate Upton proved that sometimes less is more.
In her elegant emerald gown and her minimalistic hat, Upton looked as though she was ready to depart on a glamorous summer holiday.
In 2016, Gayle King hit the red carpet in a soft blue flower hat.
The TV personality and journalist coordinated the piece with the blue tones in her printed dress.
Entrepreneur and producer Courtney Sixx took Derby hats to a new level in 2016.
A giant flower extended off the side of the hat in an extravagant display of pink and white.
Swedish model Ellen Nordegren secured an ivory fascinator to her gently waved hair for the 2016 Kentucky Derby.
The model’s choice of hat was embellished by flower petals and a veil.
In 2017, this expansive rose headpiece balanced flat across a woman’s head.
The thin frame consisted of red roses and white flowers.
Actress Laura Bell Bundy opted for a simple, yet chic red fascinator hat in 2017.
Her red and black selection served as a striking accent piece to her garden-inspired minidress.
Dimension made this woman’s hat a standout look during the 2017 Kentucky Derby.
Arranged atop a sheer wide-brimmed hat were delicate layers of fabric dyed violet and magenta.
Singer and actor Johnny Gill smiled with a guest who gave off Swan Lake vibes in her gorgeous feathered hat.
The dramatic headpiece was also decorated with a simple veil.
One does not go to the Kentucky Derby to blend in.
The bold colour choice was replicated in her shawl, her midi dress, and the wash of colour coating her lips.
One Derby-goer wore an exquisite hat that resembled more of a peony perched on the side of her head.
Soft salmon tones in the hat coordinated with her bubblegum-pink outfit.
Kentucky Derby Princesses and Queens posed in matching floral dresses and pink wide-brimmed hats.
Each year, the Derby Festival’s Royal Court program selects five women from over 100 applicants to be the Kentucky Derby Princesses, according to the Kentucky Derby Festival.
This attendee abandoned the pastels of spring for a vibrant pink and orange hat.
The onlooker matched her fabulous hat to her vibrant off-the-shoulder ensemble, which also showcased the delicate string of pearls around her neck.
Food Network’s Giada De Laurentiis wore a full-brimmed yellow hat in 2017.
The chef, writer, and TV personality smiled at Churchill Downs.
Not even a hooded raincoat could hinder this devoted Kentucky Derby fan from sporting a fabulous hat at the 2017 event.
Her neon-yellow hood made the accessory pop.
Katie Couric brought a pop of pink to the Kentucky Derby red carpet in May 2017.
Her bright-pink fascinator matched the ruffled detailing of her dress.
Miss America Cara Mund went with a floral fascinator in May 2018.
She also wore a matching fuschia dress and strappy white sandals.
This attendee perfectly matched her jewellery to the orange feathers in her hat.
The orange added a pop of bright colour to the navy-blue ensemble.
Some people still braved the rainy days in 2018 to show off their elegant designs.
This racegoer went with a blooming pink flower design.
Laila Ali arrived in a bold-red ensemble in May 2018.
She paired an angled black fascinator with a deep-red dress and black heels.
Both Star Jones and Ricardo Lugo walked the red carpet in impressive hats.
Lugo went with a classic design, while Jones stole the show in a hat adorned with colourful floral embellishments.
Victoria Justice wore a black hat with a feathered halo in May 2018.
She paired the hat with a sleek white jumpsuit and a black studded handbag.
A floral arrangement was front and centre on a spectator’s hat in 2019.
The attendee made sure her oversized hat made a statement at last year’s race.
Jennifer Nettles paired her lilac dress with a pastel pink fascinator.
The Sugarland singer’s fascinator matched the pink detail in her shoes.
Michelle Williams tried to match the colours of her dress to the ones in her hat.
The singer and actress paired her peach hat with a cute high-low pleated floral dress.
In 2019, this attendee wore a rose hat with multiple components.
The hat was covered in roses and was designed with four separate buds.
Star Jones’ hat in 2019 featured feathers and frill.
Jones’ extravagant hat was the perfect accessory for her black-and-white dress.
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