Win Big on Race Day With the Best Kentucky Derby Hats

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We're (almost) off to the races! The Kentucky Derby and all it entails (hello, mint juleps) is fast approaching—and though the day is technically about the horse racing, the first Saturday of May simply wouldn't be the same without the grand fashion choices. Specifically, we're talking Kentucky Derby hats and fascinators. Yes, your spring dresses should have their moment, but the real star of the show is what's on top! Whether they're adorned with feathers and flowers or a birdcage veil, these accessories are all about making a statement. Once you've chosen a fancy headpiece, your midi dresses, smocked dresses, or floral dresses can follow.

So, whether you're headed to Churchill Downs or celebrating at home with a spread of all the winning Kentucky Derby foods, browse here to find the best Kentucky Derby hats to elevate your ensemble. This year, you'll really want to go all out, because the big race is celebrating its 150th running! You can do that with the show-stopping toppers on this list.

There are classic straw hats with big embellishments along with fabulous fascinators in the most vibrant shades. Embody the meaning of over-the-top in an oversized, abstract headpiece or lean into vintage vibes by donning flat hats decorated with bows. We've even included a hat fashioned as a huge flower and a headband with fluttering butterflies. After all, there's no need to be subtle. No matter the style you choose for the event, we're placing our bets on these picks.

Bucket Bowler Hat

While Derby hats now come in all shapes and sizes, it's always great to get back to the classics. Though retro in design, this bowler hat is still wonderfully ornate with its satin fabrication, asymmetric roll-brim, and rosette bow embellishments.

Teardrop Fascinator

A teardrop shaped base adorned with delicate feathers and bows will give all the glamour! You can also secure it easily and firmly with your choice of a hair clip or headband.

Feather Net Mesh Fascinator

Talk about a striking silhouette! Details like cascading feathers, lovely little rosettes, and a birdcage veil make this fascinator worthy of its own Triple Crown trophy. The light pink color adds such a spring-y touch, too.

Wide Brim Derby Fascinator

Keep things effortlessly elegant with this vintage-inspired flat hat that's designed with a wide brim and ribbon detailing. No matter what you pair it with, you'll look oh so classy at your event.

Oversized Organza Hat

"Go big or go home" is truly the motto of Kentucky Derby style—and this hat definitely fits the bill. That's thanks to an enormous organza brim with elements like fabric ruffles, florals, and netting.

Vineyard Vines Kentucky Derby Fascinator Sun Hat

Going all out for Derby Day? Though it's a bit pricier, this straw hat makes for such an elegant option. Just look at those stunning floral and feather details along the veil. And while it looks like a hat, this one is actually mounted to a headband so that it stays firmly in place.

Sinamay Feather and Flower Fascinator

Since red makes up the official color palette of the Kentucky Derby, you can't go wrong with a bright ruby headpiece. Decorated with petals, ribbon, and tulle detailing, this one will certainly make a sophisticated statement.

Feather Fascinator

An abstract shape is always a Derby "do!" This one is composed of ribbon knots and elegant feathers. And since it comes with both a bendable headband and hair clip, you know it'll stay secure.

Flower Mesh Headband and Clip

If you don't want to commit to a huge hat at the racetrack, you can look towards understated style instead. Classic elements like a rosette, wispy feathers, delicate beads, and a small veil make this one a winner.

Straw Wide Brim Fascinator Hat

Not one for feathers and florals? You can still "wow" the crowd when wearing a unique shape. Along with the silhouette, a straw fabrication, and bright hue make this one so very charming.

Large Flower Fascinator

Considering the Kentucky Derby is also known as the "Run for the Roses," this jumbo flower fascinator is more than fitting! It comes in several colors and includes both a clip and a headband so you can attach it using your preferred method.

Organza Kentucky Derby Hat

This organza option will keep your head cool on that hot Kentucky afternoon so that you can remain comfortable while still turning heads. And with so many color options, you can match any outfit you choose.

Bellissima Millinery Collection Net Fascinator

It hardly gets trendier than a pretty pink bow! Lean into the popular coquette aesthetic when you wear this headpiece featuring a darling ribbon paired with delicate netting.

Feather Fascinator Headband

Vibrant pink and orange stripes finished off with feathers makes this one anything but subtle—and on Derby Day, that's the whole point!

Butterfly Fascinator

If you love butterflies just as much as Ree, this is the fascinator for you! The fluttering friends are attached to a headband for convenient, eye-catching all-day wear.

Polka Dot Bucket Hat

The polka dot pattern helps this hat stand out from the rest! Pair it with a minimal outfit and you'll have the chicest look at Churchill Downs.

Wide Brim Dress Hat

transparent layers keep this one light and springy despite the wide brim and voluminous ruffles. While pale yellow is so pretty, it comes in plenty of other shades, too. It also has a convenient drawstring adjuster inside.

Bellissima Millinery Collection Crinoline Fascinator

The oversized look of this fascinator with its feather accents atop a big, scalloped design is sure to captivate onlookers! It comes in neutral black and white as well as a bright fuchsia.

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