Kim Kardashian
Back in 2009, the Keeping Up With the Kardashians star couldn't help but explore the annual festivities in Kentucky.
Jessica Simpson
When she was with Nick Lachey back in 2004, the Hollywood couple placed their bets at the race track.
Larry Birkhead & Dannielynn Birkhead
The Derby isn't complete without this famous father-daughter duo. 2013 was no exception as the pair went for bright, colorful looks.
Tara Lipinski & Johnny Weir
If there's one pair that never disappoints during Derby weekend, it has to be these two Team USA Olympic athletes.
Josh Groban & January Jones
Throwback alert! Rewind to 2005 when this pair was a couple and nailed their festive weekend attire.
Kendra Wilkerson, Bridget Marquardt, Hugh Hefner & Holly Madison
Back in 2008, the Girls Next Door stars headed to Kentucky with several looks we'll never forget.
Miranda Lambert
We're still not over the "Little Red Wagon" singer's look from 2014.
Bethenny Frankel
Cheers to the B! The Real Housewives of New York City star doesn't disappoint with her 2009 outfit.
Sarah Hyland
Back 2015, the Modern Family star proved you can look cute and comfortable for the Derby red carpet.
Joey Fatone
We never want to say "Bye, Bye, Bye" to this 'N Sync member's attire from 2013.