The Most Glorious and Over-the-Top Kentucky Derby Hats Ever

Alexa, play "Defying Gravity."

kentucky derby "talk derby to me" hat
(Image credit: Getty Images)

Technically, the Kentucky Derby is about horse racing. But let's be real: The hats—wildly oversized, detailed, and artistic—steal the show. While wearing a hat was once a functional choice for attendees (it often gets hot!), it soon shifted into an opportunity to perform social status. And then it became something close to parody, with attendees competing to wear the most magnificent headwear. To pair perfectly with your mint julep, I present: the most extravagant and OTT Kentucky Derby hats.

Dapper Flowers

kentucky derby flower short hat

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We begin with this sweet, dapper moment. A boater straw hat is the perfect platform for a bunch of roses all around the brim. The red in the plaid blazer matching the flowers in the hat is a nice thematic touch—well done, sir, for showing us how it's done.

White on White

kentucky derby white hat

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Who says white has to be boring? (Technically, I think the crown is gray, but who cares?) The point is, layers of sheer white ribbon round about a broad brim, plus some delicate white buds laid over top, is a counter-intuitive way to be both eye-catching and subtle.

A Veil

kentucky derby red veil

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If an enormous headpiece isn't your style, how about a smaller fascinator with a pretty veil to go in front? The color is what keeps it feeling more "Derby" and less "fancy wedding," and this guest wisely chooses to lean in and match her lip color to her headpiece.

Big Sheets

kentucky derby yellow hat

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This hat could very easily be a part of the "strangest Kentucky Derby hats" list (there's a fine line between over-the-top and just plain weird), but I think we're juuuust edging back into cool with the gathering of multicolored feathers and flowers at the front. The sides feel a bit manta ray-ish.

A Floral Racetrack

kentucky derby red horse hat

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Floral boater hats on gentlemen are popular, turns out, and we can see why. When you position a tiny horse figurine, it literally looks like it's running circles around your head. The flowers are a matte cloth (instead of something shinier), which helps this look more homespun.

Best Buds

kentucky derby buds hat

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Are you feeling inspired by a literal vase of flowers? Excellent. Really lean into the vertical space with some fake fronds extending vertically from your fascinator. (I'm actually being serious here: The way to make this look substantial is either with a lot of stems or a lot of height. Or both.)

Graphic Black-White

kentucky derby black white hat

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While you often see hats with a lot of color, this guest chose something that—while visually exciting—matches her black and white dress. Simple graphic style doesn't have to mean boring, thanks to the delicate layering of the ribbon and what looks like clear beads studded throughout.

Not Boring Beige

kentucky derby beige hat

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If you want to explore a more neutral palette, like if your outfit is more colorful and you'd rather not draw focus from it, this textural cheese cloth-esque material makes for a cool base for a hat. The layers on layers keep it from looking like a hat you'd actually garden in.

Mellow Yellow

kentucky derby yellow hat

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A bright and vivid hue like this doesn't need a ton to dress it up. The floral design is bare bones and minimal, so as not to pull focus from the (extremely wide) brim. Go with a surprising, but complementary, color in your dress. No one will ever lose you in a crowd!

A Dinner Plate

kentucky derby pink bowl hat

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I really enjoy this throwback hat structure (it's very reminiscent of the hats Queen Elizabeth used to wear), which feels like a nice bowl filled to the brim with flowers. It's a particularly nice choice if the rest of your outfit isn't a throwback, like the hoop earrings and chain necklace here.


kentucky derby ostrich hat

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Ostrich feathers aren't exactly a novel hat decoration, but with the addition of some chaos, it can look like a cool art installation. The blue pin at the center, plus the haphazard arrangement of the feathers, make this look like an explosion instead of an overly designed piece.

Big Red

kentucky derby red hat

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Doesn't this kind of look like an homage to a red soda can?? If "goofy" and "outlandish" really speak to you, then by all means: decorate your red flower hat with matching feathers on the edge and—what else—a huge red flower on top. Semi-related: I love the thematic necklace.


kentucky derby pink dots hat

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Am I wrong, or does this feel like something Princess Diana might have worn back in the day? There's something about the polka dots (contrasting with the gingham dress, which is a nice touch), and the big pink pleated brim, that makes this feel vintage in a great way.


kentucky derby fuchsia hat

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Should you want to eschew the more popular red, go a few shades over on the color wheel and pick a deep, rich pink instead. The variety in hues (magenta in the feathers, raspberry in the feathers) gives it dimension and richness without looking like a bridal bouquet.

An Optical Illusion

kentucky derby black white hat

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You know those black and white pictures that just look like a swirl of black and white stripes, and the harder you stare at it, the more it looks like a house or a dog or something? Well, this is the hat version of an optical illusion picture. Stare into it, if you dare.


kentucky derby floral hat

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Does this feel like the shabby-chic section of a Michael's arts and crafts store? Sure, but I actually think that's part of its charm. The bulbous flowers, the dark brown ribbon, the woven hat: the whole thing looks like a very fancy throw pillow, but in an awesome way.

Festive Drinks

kentucky derby fish hat

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Should there be any wonder about whether this guest will be imbibing some fancy cocktails today, we are immediately reassured by the presence of actual drink glasses (and umbrellas) on her hat. I also appreciate that they're literally riding on the back of a flabbergasted fish.

A Surprising Color

kentucky derby lime hat

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When I think "Kentucky Derby hat," my mind doesn't immediately go to lime green, but that's the genius of this particular topper. The construction is cool and asymmetric, with complementary flowers on the brim, but it would have been so much more expected to choose pink or white. I salute it!


kentucky derby butterfly hat

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If you're someone with a Y2K sensibility (or you just happen to love butterflies, which is relatable) consider a fascinator that makes it look like they're floating above your head. The intricacy of the wings is the standout here, as is the fact that there are enough of them to feel substantial.


kentucky derby green hat

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I love this choice so much. The light green theme is a little surprising, given how much color you often see in the hats during the event, and choosing a thick, fleshy succulent instead of something more tender and delicate is a masterful choice. Counterintuitive, but perfect.

Architectural Flowers

kentucky derby pink flower hat

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There are a lot of floral hats at the Kentucky Derby (which makes sense; it's often a decoration on well-crafted toppers), but if you don't want to look like anyone else, supersize it. This hat is, in actual fact, beautifully delicate, but it looks like a resin sculpture.

Matching Hats

kentucky derby flower hats

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Um, if you're going to the Kentucky Derby (or just a themed party) and you're bringing a friend, it is your sworn duty to go in matching hats. With slight preference for the one on the left (there's more flowers throughout, and it's more cohesive), both are a garden party personified.

Lines of Blooms

kentucky derby purple hat

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If you're going to go with real or real-looking flowers, let them be the standout piece. This simple angled hat with a stem of flowers laid across the top (with the theme continued under the brim) is striking for the simple fact that it is so simple: It doesn't need anything else.

Red Waves

kentucky derby red wavy hat

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Now that is a fashion statement. For the glamorous Derby experience, you don't have to choose anything overly adorned. Just choose a rich color like this one, match everything to it (including your lip color), and be prepared for every single compliment.


kentucky derby flamingo hat

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If I were to actually go to the Kentucky Derby and was faced with the prospect of designing a hat that described my essence, it would be this one. A magnificent plastic lawn ornament (wearing Mardi Gras beads, naturally) plus a mini hat that looks just like mine? All yes.

A Dinner Plate

kentucky derby flat plate hat

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Apologies to this person, who probably heard the dinner plate comparison about 20 times that day, but I really do mean this as a compliment. The delicacy of the sequins and ribbon, plus the see-through mesh, actually makes this look more like a stained glass window.

Looking Like a Building

kentucky derby white floral hat

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Wearing such a rich, architectural headpiece that you immediately draw comparison to the spire of a building? Now that's a fancy hat. This one could also double as a faux wedding cake if you weren't looking too hard at it. I love the faux ladybug and butterflies!

Going Literal

kentucky derby horse hat

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A little on the nose, perhaps (on the muzzle? Sorry), but this guest is signaling to everyone that she knows exactly what event she's at. And/or that she's a big horse fan. And/or that she's really into making hats. The rose in the mouth is a nice flourish, I won't lie.

Bigger, Bigger, Bigger

kentucky derby rose hat

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You know what I'm about to say: go big or go home. And this particular guest chose to go so big that she's wearing a rose the size of a truck tire. With matching red lipstick and red dress. All of it is a 100 percent yes from me. Bonus: it doubles as a sun hat!

The Toppiest Top Hat

kentucky derby top hat

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I mean. There are top hats, and then there's this top hat, with actual plastic horses embedded in the design. I have so many questions. 1) Is it heavy? 2) Did you make it yourself, or did you actually go to a designer with this very thing in mind? 3) How do you go through doors??

An Actual Racecourse

kentucky derby green racecourse hat

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I mean...when in Rome? Crafting a cranial topper that literally just looks like the racetrack of the horses in question, with actual teeny tiny horses, is both exceptionally on the nose and just plain exceptional. My favorite part might be the paper trees on the crown??


kentucky derby horse hat

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This is the most magnificent millinery concoction in all of the event's history. It's both the best and worst Derby hat I have ever seen. It is thematic, it is incredible, it is altogether too much and yet I want more (do the horses spin??). It defies all earthly explanation. It is simply...Hat.

Katherine J. Igoe
Contributing Editor

Katherine’s a contributing syndications editor at Marie Claire who covers fashion, culture, and lifestyle. In her role, she writes stories that are syndicated by MSN and other outlets. She’s been a full-time freelancer for over a decade and has had roles with Cosmopolitan (where she covered lifestyle, culture, and fashion SEO content) and Bustle (where she was their movies and culture writer). She has bylines in New York TimesParentsInStyle, Refinery29, and elsewhere. Her work has also been syndicated by ELLEHarper’s BazaarSeventeenGood Housekeeping, and Women’s Health, among others. In addition to her stories reaching millions of readers, content she's written and edited has qualified for a Bell Ringer Award and received a Communicator Award. 

Katherine has a BA in English and art history from the University of Notre Dame and an MA in art business from the Sotheby's Institute of Art (with a focus on marketing/communications). She covers a wide breadth of topics: she's written about how to find the very best petite jeanshow sustainable travel has found its footing on Instagram, and what it's like to be a professional advice-giver in the modern world. Her personal essays have run the gamut from learning to dress as a queer woman to navigating food allergies as a mom. She also has deep knowledge of SEO/EATT, affiliate revenue, commerce, and social media; she regularly edits the work of other writers. She speaks at writing-related events and podcasts about freelancing and journalism, mentors students and other new writers, and consults on coursework. Currently, Katherine lives in Boston with her husband and two kids, and you can follow her on Instagram. If you're wondering about her last name, it’s “I go to dinner,” not “Her huge ego,” but she responds to both.