All The Extravagant Hats At The 150th Kentucky Derby Do Not Disappoint In The Slightest

Derby hats
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The ostentatious opulence and downright decadence fueled by mint juleps and avarice at the Kentucky Derby are enough to make anyone’s head spin without the aid of the Run for the Roses’ booze of choice.

However, if you can get past all that, there is something to be said for the impeccable fashion sense of the rich and the famous when it comes to the mind-melting headgear they rock annually at Churchill Downs for the big race.

Thanks to the round-up prowess of several other contributors on the social medias, we have ourselves a look at the best hats from this year. Once again, they are as baffling and silly as they are exceptional achievements of designing craftsmanship.

Already I’m quite impressed with the initial reveals from this year. It’s only going to escalate as the 6:57 p.m. ET post time gets closer and TV/streaming coverage ramps up. Suffice it to say, if this is a mere appetizer to the main course, we’re on track for a hell of a 2024 Kentucky Derby in terms of headdresses. Salute to the Kentucky State Police for taking on the near-impossible task of wrangling such a chaotic band of humans, too:

All those hats are pretty cool. I’m more partial to this piece of incredible memorabilia shared on Saturday: A signed Kentucky Derby hat from the owner and jockey of eventual Triple Crown winner Secretariat.

I know that’s technically not in the running for highest fashion honors at Churchill Downs. Nevertheless, what a job preserving the cap that well for all these years. Secretariat won five major races as a 2-year-old before a historic 1973 season in which he rattled off six huge victories in addition to triumphs at the Derby, Preakness Stakes and Belmont Stakes.

The force of nature nicknamed Big Red set speed records at all three of those races, winning the Belmont by 31 lengths. His time at Churchill Downs still stands as the best.

Back to the zanier brands of headgear, though. DraftKings collected some of the better ones from years past, which could easily be mistaken for being from this year in absence of any clarification to the contrary. But I digress.


For further reading and celebration of the Kentucky Derby’s famous hats, check out the piece below. Additionally, if you’ve never read Hunter S. Thompson’s piece titled, The Kentucky Derby Is Decadent and Depraved, it’s one of the greatest works of narrative pseudo-nonfiction in the history of mankind. Can’t recommend it enough.

A beer bottle on a dock



A beer bottle on a dock