Stylish Hats and Fascinators to Wear to the Kentucky Derby

Kentucky Derby 144 - Atmosphere
The Best Kentucky Derby HatsRobin Marchant - Getty Images


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It goes without saying, but no Kentucky Derby outfit is complete without a show-stopping topper. We're talking fun fascinators with feathers and flowers galore; over-the-top hats in vivid shades with wide rims and chic tulle; statement headbands with embellishments... the list can go on and on. Whether you're heading to Churchill Downs to take part in the horse race-watching festivities (our editors' highly recommend!) or hosting a party of your own at home, here are some of the best Kentucky Derby headpieces to wear on the first Saturday of May.

Organza Kentucky Derby Hat

transparent layers keep things light even with a major hat moment.

<p><a href="https://www.amazon.com/dp/B01CNTHKRQ?tag=syn-yahoo-20&ascsubtag=%5Bartid%7C10067.g.9267914%5Bsrc%7Cyahoo-us" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>Organza Kentucky Derby Hat </p><p>amazon.com</p><p>$23.99</p>

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Organza Kentucky Derby Hat

amazon.com

$23.99

Custom Butterfly Headpiece

Be the talk of the town with a custom fluttering headpiece inspired by Princess Beatrice's famous butterfly topper.

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.etsy.com%2Flisting%2F234608302%2Fcustom-butterfly-headpiece-inspired-by&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg9267914%2Fbest-kentucky-derby-hats-and-fascinator-headbands%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>Custom Butterfly Headpiece</p><p>etsy.com</p><p>$249.95</p><span class="copyright">Courtesy FabHatters /Etsy</span>

Jumbo Bow Sinamay Hat

A bold bow is always a Derby "do."

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.etsy.com%2Flisting%2F511277087%2Fm612-redblack-kentucky-derby-church&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg9267914%2Fbest-kentucky-derby-hats-and-fascinator-headbands%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>Jumbo Bow Sinamay Hat</p><p>etsy.com</p><p>$215.00</p>

White Navy Fascinator

Neutral colors will let dramatic embellishments stand out.

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.etsy.com%2Fuk%2Flisting%2F616471842%2Fwhite-navy-fascinator-kentucky-derby-hat&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg9267914%2Fbest-kentucky-derby-hats-and-fascinator-headbands%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>White Navy Fascinator</p><p>etsy.com</p><p>£245.29</p>

Giant Soft Pink Flower Fascinator Hat

Why wear a hat decked in roses when you could wear a headpiece that's one giant rose?

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.etsy.com%2Flisting%2F1020682499%2Fgiant-soft-pink-flower-fascinator-hat&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg9267914%2Fbest-kentucky-derby-hats-and-fascinator-headbands%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>Giant Soft Pink Flower Fascinator Hat</p><p>etsy.com</p><p>$299.67</p>

Straw Headpiece for The Races

If you're not a feathers and florals type, you can still make a statement with a unique shape.

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.etsy.com%2Fuk%2Flisting%2F586062428%2Fstraw-headpiece-for-the-races-elegant&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg9267914%2Fbest-kentucky-derby-hats-and-fascinator-headbands%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>Straw Headpiece for The Races</p><p>etsy.com</p><p>£462.54</p>

Elegant Sunny Yellow Fascinator

High-impact color is an absolute no-brainer for the Derby.

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.etsy.com%2Flisting%2F1205842283%2Falice-elegant-sunny-yellow-fascinator&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg9267914%2Fbest-kentucky-derby-hats-and-fascinator-headbands%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>Elegant Sunny Yellow Fascinator</p><p>etsy.com</p><p>$134.96</p>

Pink and Orange Bow Fascinator

There are moments in life that demand the subtle and understated. The Kentucky Derby is not one of those moments.

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.etsy.com%2Flisting%2F571445030%2Fpink-and-orange-bow-fascinator-oversized&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg9267914%2Fbest-kentucky-derby-hats-and-fascinator-headbands%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>Pink and Orange Bow Fascinator </p><p>etsy.com</p><p>$202.38</p>

Purple Flower Fascinator Hat

Bring a spring-y touch to derby day with a fascinator packed with florals.

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.etsy.com%2Flisting%2F1179560683%2Fpurple-flower-fascinator-hat-kentucky&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg9267914%2Fbest-kentucky-derby-hats-and-fascinator-headbands%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>Purple Flower Fascinator Hat</p><p>etsy.com</p><p>$180.00</p>

Allira Voilette Headband

It's "go big or go home" when it comes to Kentucky Derby style, and this butterfly-embellished topper fits that motto to a T.

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.jenniferbehr.com%2Fproducts%2Fallira-voilette-headband&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg9267914%2Fbest-kentucky-derby-hats-and-fascinator-headbands%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>Allira Voilette Headband</p><p>jenniferbehr.com</p><p>$1425.00</p>

New Large Red Rose Flower Feather Teardrop Fascinator

The winner of the Derby gets a garland of roses, so why not wear a headpiece that serves as one of your own?

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.etsy.com%2Flisting%2F1244708974%2Fnew-large-red-rose-flower-feather&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg9267914%2Fbest-kentucky-derby-hats-and-fascinator-headbands%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>New Large Red Rose Flower Feather Teardrop Fascinator</p><p>etsy.com</p><p>$72.90</p>

Light Blue Kentucky Derby Hat

Between the powder blue hue and the elegant feathers, this hat is sure to turn heads.

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.etsy.com%2Flisting%2F1410867529%2Fm936-light-blue-hat-kentucky-derby-hat&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg9267914%2Fbest-kentucky-derby-hats-and-fascinator-headbands%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>Light Blue Kentucky Derby Hat</p><p>etsy.com</p><p>$325.00</p>

Ivory Pearl Headband

Go in an entirely different direction with a Middleton-esque headband, modernized with fun embellishment.

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.lelesadoughi.com%2Fcollections%2Fjeweled-headbands%2Fproducts%2Fpearl-headband-2&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg9267914%2Fbest-kentucky-derby-hats-and-fascinator-headbands%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>Ivory Pearl Headband</p><p>lelesadoughi.com</p><p>$150.00</p>

Exquisite Fascinator Derby Hat for Women with Golden Flower

A straw hat—such as this elegant option with feather details—is a classic look for the Derby.

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.etsy.com%2Flisting%2F1203570283%2Fexquisite-fascinator-derby-hat-for-women&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg9267914%2Fbest-kentucky-derby-hats-and-fascinator-headbands%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>Exquisite Fascinator Derby Hat for Women with Golden Flower</p><p>etsy.com</p><p>$228.00</p>

Josephine Fascinator

If there was every a time to give Barbie pink a go, it would be at the Kentucky Derby.

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.hobbs.com%2Fus%2Fproduct%2Fjosephine-fascinator%2F0124-3041-040000-CARNATION-PINK.html%23cgid%3Daccessories-hats%26is%3Dtrue%26sz%3D60%26start%3D0%26isSecondPage%3Dfalse%26pid%3D0124-3041-040000-CARNATION-PINK-1SIZE%26pos%3D5&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg9267914%2Fbest-kentucky-derby-hats-and-fascinator-headbands%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>Josephine Fascinator</p><p>hobbs.com</p><p>$157.50</p>

Bow Midi Disc Fascinator

This poppy red fascinator is anything but subtle... and that's the point! You'll stand out in the crowd when you top your look with this cheery head topper.

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.phase-eight.com%2Frow%2Fproduct%2Fbow-midi-disc-fascinator-705979682.html%23q%3Dfascinator%26is%3Dtrue%26sz%3D60%26start%3D0%26isSecondPage%3Dfalse%26pid%3D70597968200%26pos%3D8&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg9267914%2Fbest-kentucky-derby-hats-and-fascinator-headbands%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>Bow Midi Disc Fascinator</p><p>phase-eight.com</p><p>$95.00</p>

Magenta Pink Kentucky Derby Hat Fascinator

Take a page out of the British royal family's style book with a feathered fascinator.

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.etsy.com%2Flisting%2F1678554683%2Fmagenta-pink-kentucky-derby-hat&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg9267914%2Fbest-kentucky-derby-hats-and-fascinator-headbands%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>Magenta Pink Kentucky Derby Hat Fascinator</p><p>etsy.com</p>

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