17 Best Kentucky Derby Hats

1

best wide-brim fascinator

Wide Brim Fascinator

1

best wide-brim fascinator

Wide Brim Fascinator

There's something to be said for the woman who wears a classically elegant fascinator to the Derby, and it's definitely not that she's boring. Let your dress or jewelry steal the show and have this hat be the cherry on top of your stunning outfit.

2

best headband

Looped Headband Fascinator

2

best headband

Looped Headband Fascinator

Now 55% Off

If this is your first Kentucky Derby experience (how exciting!), then it's totally reasonable to be hesitant to go all out with your hat. If you'd prefer something a bit more subtle, we'd recommend a headband like this. It's not as overwhelming as a traditional fascinator but still provides the elegant touch that's expected for the big day.

3

best feathered fascinator

Organza Feather Clip Fascinator

3

best feathered fascinator

Organza Feather Clip Fascinator

On the flipside, if there's one time a year that you can go all out with your fashion statements, it's the Kentucky Derby. While feathers and bows might be a bit too much any other weekend out of the year, this one was made for the most show-stopping fascinators you can find.

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4

best splurge wide-brim hat

Lilliana Hat

4

best splurge wide-brim hat

Lilliana Hat

If you've been to the Derby before then you know it can get quite hot in the afternoons. A wide-brim hat like this makes those late-spring afternoons in the South a bit more bearable by providing plenty of shade.

5

best budget wide-brim hat

Bowknot Straw Hat

5

best budget wide-brim hat

Bowknot Straw Hat

If you'd rather splurge on your dress or jewelry than your hat but still want some coveted sun protection, then snag this inexpensive option on Amazon. It still provides plenty of shade and the adorable black bow adds a sophisticated touch that makes it perfect for the Derby.

6

best pillbox fascinator

Loop Bow Pillbox Fascinator

6

best pillbox fascinator

Loop Bow Pillbox Fascinator

Now 40% Off

The iconic hat of Jackie O. has found new life in the realm of fascinators for the Derby. The shape of this one is a bit more subdued in comparison to her extra-large circular fashion statements, but the bow gives it plenty of height and dimension.

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7

best veiled fascinator

Kentucky Derby Veiled Fascinator

7

best veiled fascinator

Kentucky Derby Veiled Fascinator

A veil adds such an elegant touch to the usual fascinator. It can take your hat from blending in with the crowd to a total showstopper in no time.

8

best for color selection

Wide Brim Hat

8

best for color selection

Wide Brim Hat

Now 50% Off

Get ready for everyone to ask you where you snagged this sophisticated yet chic organza hat. We'll keep your secret that it was under $10 on Amazon.

9

most unique fascinator

Loop Detail Headband Fascinator

9

most unique fascinator

Loop Detail Headband Fascinator

Now 35% Off

While we'd suggest keeping your fascinator to a single color if you go with a patterned dress, that in no way means that your hat needs to be boring! This fun headband proves that a single hue can make quite the statement.

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10

most subtly elegant fascinator

Fascinator

10

most subtly elegant fascinator

Fascinator

Now 17% Off

Perfect for the lady that wants to respect Churchill Downs's traditions but isn't comfortable with a lot of the over-the-top hats that can be found there, this elegant black number blends traditional motifs with modern chic.

11

most traditional fascinator

Kentucky Derby Hat

11

most traditional fascinator

Kentucky Derby Hat

Is there anything worse than splurging on the perfect dress and shoes only to remember last-minute that you totally forgot your hat? That's when this under $35 find comes in handy. No one will guess you got it on Amazon.

12

most sophisticated design

Pleated Spiral Trim Fascinator

12

most sophisticated design

Pleated Spiral Trim Fascinator

Now 17% Off

So many fascinators have a similar upturned style and, while we love it, it's always fun to mix it up a bit, right? This downturned fascinator brings a bit of a 1920s style to the Downs.

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13

most traditional headband

Fascinator on a Headband

13

most traditional headband

Fascinator on a Headband

This fascinator brings so many classic elements to the table in the most elegant way: a rosette, wispy feathers, and a small veil. And all for under $20!

14

best organza hat

Organza Derby Hat

14

best organza hat

Organza Derby Hat

Not all the wide-brim hats on the market are some form of straw. This organza option will let a gentle breeze flow through, perfect for those hot Kentucky afternoons.

15

best flower fascinator

Kentucky Derby Fascinator

15

best flower fascinator

Kentucky Derby Fascinator

Why have a flower on your hat when your hat can be the flower itself? This classic rosette is larger than life in the best way.

Hannah Jones is the Commerce Editor for Country Living. Her eye is always on the next up-and-coming products to include in gift guides and she's ready to test everything from dog beds to garden tools for product reviews. When she’s not scoping out the latest and greatest items on the market, you can find her hanging with her two rescue dogs.

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