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
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
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
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
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
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
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
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
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
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
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.
Ostrich
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
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.
Dots
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.
Fuchsia
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
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.
Cottagecore
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
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
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!
Butterflies
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.
Succulents
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
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
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
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
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.
Flamingoes
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
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
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
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
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
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
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??
This!!
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.
