38 Photos Of Celebs At The Kentucky Derby That Show Just How Random The Guest List Is

LOUISVILLE, KY - MAY 02: Kris Jenner and Kim Kardashian arrive at the 135th Kentucky Derby at Churchill Downs on May 2, 2009 in Louisville, Kentucky. (Photo by Jeff Gentner/Getty Images)
Source: Jeff Gentner/Getty Images Entertainment/Getty Images

It's the most wonderful time of the year, ladies and gentlemen, when sports fans, horse lovers, and crazy hat aficionados join forces on one exciting day to watch the fastest two minutes in sports. Yep, it's the Kentucky Derby, always held on the first Saturday in May, and it's a sight to be seen. Of course, the event is technically about the actual horse race, but let's be real, it's also so much fun to watch the entire spectacle of it all. The colorful dresses! The exciting parties! Those massive hats. Like any other widely publicized event, the Kentucky Derby attracts hordes of random celebrities that will have you wondering why, exactly, they're there.

There's no secret, really — celebrities love a hip and happenin' event, and the Kentucky Derby is a particularly glamorous one. The chance to party in your Sunday best on a Saturday, mint julep in hand, in the springtime sun does sound totally appealing. But since most of us normals will never get the chance to attend the elite Kentucky Derby parties, I'm totally giving you permission to live vicariously through these photos of random celebs in completely ridiculous outfits, from pastel plaid tuxes to hats with feathers. 

1. Kim Kardashian & Kris Jenner

Kardashian and her momager attended the spectacle in 2009, which actually shouldn't be too surprising because if there's a celebrity-studded party somewhere in the world, a Kardashian will be there.

2. Spencer Pratt & Heidi Montag

Hey, it was 2008. The Hills were alive and well.

3. Lauren Conrad

Hat game on point, but would you expect any less from the fashion mogul?

4. Salt-N-Pepa

Ooh, baby, baby. 

5. Kendra Wilkinson, Bridget Marquardt, Hugh Hefner, & Holly Madison

The girls next door left the Playboy Mansion to travel to Kentucky in their pastel-colored best.

6. Nicole Richie

Richie's 2004 ensemble included a baby yellow pantsuit, which I'm living for, actually.

7. Tara Lipinski, Vanessa Minnillo, Nick Lachey, & Johnny Weir

This photo of two former Olympic ice skaters and the Lacheys with their kooky hats (Nick, where's your hat?) is something that could only happen at the Kentucky Derby, I reckon.

8. Joey Fatone

This outfit. I have no words. Apparently, Fatone is a staple at the celebrations each year — and he's always clad in outfits right out of a '50s musical.

9. Nick Lachey & Jessica Simpson

Though he's since attended the Derby numerous times with now-wife Vanessa Lachey, once upon a time in 2004, Lachey's date was ex-wife Jessica Simpson, bringing me all the early '00s nostalgia feels. Also, that hat was an A+ choice, girl. Lachey seems anti-hat, for some reason, which is a bummer.

10. Miranda Lambert

The country darling is a frequent and enthusiastic guest at Derby celebrations, which makes total sense given that she's an equestrian herself — she owns three horses and a plethora of other farm animals of her own. Lambert recently told Horse Channel, "When I'm riding, it clears my head and I'm able to write better music. I love being outside. It's always good to get away from the computer and cell phone and just enjoy being with my horses."

11. Star Jones

Talk about a throwback... remember the controversial co-host of The View? Turns out, she's a huge fan of the Kentucky Derby. She's spotted there year after year.

12. Ashanti

The R&B crooner stepped out in a Derby-approved look in 2006.

13. Kellan Lutz

The actor looked dapper in his newsboy cap in 2012.

14. Adrian Grenier

Grenier appeared sans-Entourage but cozied up to then-girlfriend Isabel Lucas in 2008.

15. P. Diddy

No one loves a good party more than Diddy, so it's not a shocker that he'd flock to Kentucky to roll with fellow ballers.

16. Melissa Joan Hart

In 2007, Hart joined the crowds for a red carpet photo op on race day.

17. Mary J. Blige

The singer worked a head-to-toe red look, and I'm digging it.

18. Eli Manning & Carson Daly

Not sure if these guys planned to color-coordinate so well, but if so, I applaud their efforts.

19. Debra Messing

Messing was ready for a day at the races in 2012.

20. Ashlee Simpson & Pete Wentz

Ashlee wasn't the only Simpson down for the Derby, bringing ex-husband Wentz as her date in 2010.

21. Ginnifer Goodwin

Goodwin gets points for matching her hat and her eye shadow to her dress.

22. Queen Elizabeth

The Royals are no strangers to a crazy hat situation and a jovial sporting event, so it shouldn't come as much of a surprise that the Queen wanted to join in on the festivities in 2007.

23. Jaime Pressly

The actor was off to the races in 2006.

24. Paris Hilton & Doug Reinhardt

The former couple brought out their finest "funeral or Derby?" attire for the 2009 celebration.

25. LeAnn Rimes

The country singer donned her best large bonnet for the occasion in 2009.

26. Mario & Courtney Lopez

The actor/host shared a moment with his now-wife Courtney in 2010.

27. Kid Rock & Pamela Anderson

The former spouses attended the Derby a few times together before their divorce in 2006.

28. Usher

Usher was ready to party during the 2005 races.

29. Brooke Shields

The actor made it a family affair in 2009.

30. Marisa Miller

Naturally, the model stunned in her Derby best.

31. Molly Sims

Sims nailed the Derby look in 2008.

32. Paula Patton

Patton looked pleased as punch to wear her oversized hat in 2011.

33. Maria Menounos

The TV host opted for an Alice in Wonderland-themed getup, and I love it.

34. Ruben Studdard

The American Idol winner looked effortlessly sharp in his bow tie and hat combo.

35. Ice-T & Coco

The E! couple made a picture perfect pair in 2012.

36. Tori Spelling & Tara Reid

The two ladies shared a secret on the red carpet... was it about where they stashed their big hats?

37. Kate Gosselin

Gosselin rocked a Victorian-style hat in 2011, feathers and all.

38. Guy Fieri & Aubrey O'Day

What I wouldn't give to be a fly on the wall during this photo op.

I think it's safe to say that the Kentucky Derby brings out a pretty vast assortment of celebrity spectators looking for a good time, and I'm a bit jealous. I wonder who will make an appearance at this year's festivities.

Must Reads