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The Kentucky Derby is the year's best fashion show that just happens to have a horse race at the end. Derby Day at Churchill Downs is a place to see and be seen, with jetsetters and horse owners showing off their finest fashion in the grandstands and the upper-level suites while the proletariat carouse in the booze-soaked infield -- where pretty much anything goes. A high-end custom-made Derby hat will set you back between $500 to $1,000 -- a drop in the bucket, of course, to the billionaires, millionaires and celebs who show up every year at Churchill Downs to bet on the big race. With the 144th "Run for Roses" finally here, we thought it would be fun to show off the best and biggest hats and the wildest looks from the 2018 Derby and previous Derby Days.
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Hey, if you want to turn your beard into a kraken or wear 800 bows on your head, it's all good at Churchill Downs.
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It's gonna be close, but this woman is definitely in the running for biggest fake flower on a hat at this year's Derby.
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Johnny Knoxville and Johnny Weir walk the red carpet at the 2018 Derby.
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A derby patron wears her lat low to keep it from blowing off in the wind.
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Laila Ali is resplendent walking the red carpet at the 2018 Derby -- though how is that hat staying on?
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Von Miller is looking good on the red carpet at the 2018 Derby.
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Look at this friggin' guy. The Pepto-Bismal pink jacket and the bow tie just really round out this look.
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Pastels? We don't need no pastels.
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These dudes would have fit right in at the first Kentucky Derby back in 1875.
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The infield at the Kentucky Derby is like the lower decks on the Titanic -- way more fun than first class and a lot more germs.
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"Day 4 behind enemy lines: I really can't see out of these sunglasses, but they look so cool."
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Seriously, you couldn't at least try to color coordinate?
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Ms. Peacock, with the horseshoe, in the stable.
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This hat is great for keeping the sun off your shoulders.
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Without any context, you might think these two were attending a royal wedding.
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Miss America winner Betty Cantrell blows a kiss on the red carpet before the 2016 Kentucky Derby.
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Former Playboy Playmate and TV personalty Kendra Wilkinson shows off her hat on the red carpet before the 2015 Kentucky Derby.
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Do these even qualify as hats? Who cares -- they're awesome.
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People of Walmart has got nothing on the infield at the Derby.
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If you come from the campy world of figure skating, you get to wear outfits like this every day, not just on the first Saturday of May.
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This Derby hat also works great at a funeral.
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NFL Hall of Famer Warren Moon, looking dapper in his Derby ensemble, walks the red carpet at Churchill Downs in 2015.
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This hat has the exact arc of a dolphin jumping out of the water. And it's glorious.
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This patron's purple hat legitimately looks like a tree you would see in Whoville.
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"I literally don't know. My hat is slowly folding in on itself and swallowing my head whole."
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It looks like this hat just got struck by lightning in a cartoon. Relax a little bit.
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Little-known fact: The winner of the Derby will end up getting this hat.
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The more she twists that thing around, the tighter it's going to end up on her head.
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You DO NOT want to be seated behind this woman in the grandstands at Churchill Downs.
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If you look close, you can see the outline of a straw hat underneath the bridal shower centerpiece that this woman is wearing on her head.
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Remember those dioramas that you had to make in grade school? Yeah, this one's definitely getting a good grade.
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There are 10-gallon hats and then there's whatever this is.
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Remember the hats that Damon Wayans' character, Blaine Edwards, wore on "Men on Film" during the heyday of "In Living Color." C'mon, of course you do. We give this hat two snaps and a twist because you can't mess with this.
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Joey Fatone actually wears jackets like this every day -- this day just happened to be Derby Day.
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Gronk's probably still upset that they didn't have a horse No. 69 that he could bet on.
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We're not entirely certain, but there may actually be a live peacock on that woman's head.
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Who wore it better?
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When you ransack Hobby Lobby to make your Derby hat.
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This guy nails it.
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Check out the sweet tattoo on Grandma!
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Julia Roberts would have looked great in this one.
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This hat would work great at a gender reveal party.
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Dannielynn Birkhead is a regular at the Kentucky Derby, if you couldn't tell from this top-shelf hat.
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Someone, somewhere, please, caption this photo.
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Is it just us, or is this floral arrangement just a little off center?
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No birds were injured in the making of this hat.
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