A Look Back at Kentucky Derby Glam

All the Kentucky Derby Glam You Need

Wide brim straw hats, floral dresses, and all-around garden elegance are some of the things one should expect from the Kentucky Derby. If you happen to be heading to the derby next week and still need inspiration, you might want to get into these derby glam looks we’re about to share.

Jessica Simpson, 2004 

Remember when Jessica Simpson and Nick Lachey were married with the cutest reality TV show?! Well, back in 2004 the pair attended the Kentucky Derby. Jessica was every bit a California girl with tanned, glowing skin, pink glossy lips, and her signature blonde tresses pulled into a low ponytail. Her look was cutesy, flirty, and girly – very much so the things we came to love about her in the late 90s and early 2000s.

Nicole Richie, 2004

Speaking of early 2000s household names, Nicole Richie attended the Kentucky Derby in a not-so-girly look. In what would have been true Nicole Richie fashion back then, she wore a canary yellow pantsuit with a black felt bowler hat. If you remember Nicole at all, under eye black liner was her thing… so were thin eyebrows, glossy lips, and bleached or dyed extensions.

Zoë Saldana, 2007

Zoë Saldana was every bit of class when she attended the 2007 Kentucky Derby. She wore an off white, sleeveless pencil dress with the cutest peephole. She brought the derby drama by wearing a periwinkle blue straw hat and red lips. Best dressed!

Heidi Montag & Spencer Pratt, 2008

Remember Speidi?! In 2008, Heidi Montag and Spencer Pratt attended the Kentucky Derby as a couple during the height of their reality TV fame. Heidi wore a sleeveless, floral ruffled dress, with nude peep toe slingbacks and a hot pink floppy straw hat. She vamped up her look with heavily lined eyes, rosy pink cheeks, and glossy nude lips. As always, her blonde hair was perfectly curled for that effortless California girl vibe.

Kim Kardashian, 2009

While she was still on her climb atop the digital and beauty world, Kim Kardashian made a stop at the 2009 Kentucky Derby. In true KKW fashion, she was sexy but classy. She rocked her signature smokey eye and glossy nude lip look that she has mastered over the years. She was certainly as beautiful then as she is now.

Paris Hilton, 2009

Not one to miss out on a good time, billionaire heiress, Paris Hilton, attended the 2009 Kentucky Derby wearing a headband fascinator, a blonde shag, and her best spray tan. Over the years, Paris has kept her makeup pretty neutral, focusing mostly on her skin, rosy cheeks, and glossy lips. For the derby, that look stayed the same, no less.

Miranda Lambert, 2014

For the 2014 Kentucky Derby, Miranda Lambert was truly a lady in red. Miranda matched her makeup to her red dress, fascinator, satin pumps, and clutch. This look was bold and ready for this popular red carpet event.


Lindsey Vonn, 2016 

Now here’s a look we don’t see often at the Kentucky Derby. Olympian, Lindsey Vonn, wore what some may consider to be an edgy look for the event and we absolutely loved it! Her gold high waist sequined trousers, off-white low cut blouse, and nude wide brim hat were the perfect outfit for her smokey eye makeup, nude lips, and straight blonde hair.


We can’t wait to see who will wear what at this year’s Kentucky Derby.


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