Last Updated on April 29, 2025 by Eve Dawes
25 stunning women’s Kentucky Derby hats from oversized hats to pretty fascinators that up the fashion anti
Kentucky Derby hats for women can make or break an outfit and have the power to completely change the overall look. Whether you go for a delicate Kentucky Derby fascinator or over the top large hat, it’s the time to take a chance and have fun with fashion. There’s definitely lots of things to consider when buying your hat and finding the right style, size and color for you. Here are some top tips for finding the perfect horse racing or Kentucky Derby hats for women and the best hats to arrive at the Churchill Downs in style on Saturday.
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Do I have to wear a hat to the Kentucky Derby
While hats aren’t compulsory at the Kentucky Derby or the Kentucky Oaks like they are at a lot of English horse races, pretty much everyone wears some type of hat or fascinator embellished with feathers, flowers, or ribbon. It’s tradition that dates back to the Kentucky Derby’s start in 1875 and is believed to bring good luck.
It’s a chance for women to express their inner Southern Belle mixed with British tradition. As well as a way to create a really statement making look and have fun with fashion while keeping the sun out of your eyes.
At Louisville’s Churchill Downs, a woman’s choice of headwear often depends on where she’s watching. In the general admission infield, hats tend to be eccentric, while those in the seated areas verge toward elegant.
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What color hat should I wear to the Kentucky Derby
The Kentucky Derby is one time where you can really wear any color. The brighter and more statement making the better.
Should I buy my Kentucky hat or dress first
Hats are normally harder than dresses to shop for so the general consensus is to buy the hat first. However, that being said if you fall in love with a dress first you can always go for a neutral hat or work with a Milliner to custom design one to coordinate with your Kentucky Derby dress.
Should I wear a big hat or fascinator to the Kentucky Derby
The Kentucky Derby is a chance to go big and statement making with your hat but they’re not for everyone. A lot of the decision comes down to personal preference and your frame. However, some of the main things to consider if you’re torn between going big or small with your hat are:
- If you’re flying, how easy is it to pack?
- How good is your spacial awareness? No one wants to lose an eye.
- What do you feel more comfortable in?
- What enclosure are you in?
- If you’re petite consider a Kentucky Derby fascinator so that your hat doesn’t overwhelm you.
- How tall are you?
- How easily do you burn?
I love large hats but at 5’2″ I’ve always struggled with large brim hats as I have to crane my neck back to be able to talk to anyone and not have a hat brim obscuring my view. You’re also more likely to hit people with your hat just walking and conversing than if you’re taller than most people and able to avoid them.
The enclosure you’re in is also a consideration. If you’re sat inside in Millionaires row you don’t have to worry so much about your hat getting ruined in the rain or blowing away. If you burn easily and are going to be outside a lot you might want to go for a larger hat that offers more sun protection than a fascinator.
The Kentucky Derby is a long day, so whatever style you choose, just make sure you’re comfortable in it.
How do I find the best Kentucky Derby hat style to suit my face
Obviously the best way to find the right hat for you is to go into the store to try them on in person. You want to make sure if it doesn’t have an adjustable hat band that it fits. If it’s too big you can often find hat spacers online but if it’s too small there’s not much you can do.
You also want to make sure it suits your face shape. Different hats suit different people. There’s no one size or fit of large hats that fits all.
Lastly, you want a hat you feel comfortable in and not that feels like someone else’s style or fashion sense. As Jenny Pfanenstiel says “A hat can not only change your day, but it can also change your life!”.
If you’re unable to get to a store, I recommend fascinators over hats as they’re one size fits most and are less likely to overwhelm or underwhelm your frame. Try to order from somewhere that offers free shipping and returns so that you’re not stuck with it.
A few more tips for buying the perfect womens Kentucky Derby hat for you
After years of wearing hats to the horse races there’s definitely a few things I prefer in hats. I love net but have found when it’s too long and goes over my eyes I end up squinting and it getting caught in my lashes. They also cast unflattering shadows in photos. Instead I tend to go for hats now where the lace doesn’t come down as low.
Another thing to consider when buying your hat or Kentucky Derby fascinator is how are you going to keep it on. Especially if it’s windy! I personally prefer fascinators that are on elastics or headbands one’s that just grip on. Those grips tend to rip out your hair and aren’t effective if it’s windy.
How to style hair with Kentucky Derby hats and fascinators
I’d highly suggest doing a trial run before the actual day to make sure how you’re planning on styling it works with your hats. Some styles won’t work with a bun or updo unless you do it really low. Others you’ll have to play around with to make sure they’re secure if you’re planning on wearing your hair down.
When it comes to big Kentucky Derby hats for women, I always go for styles with adjustable bands that work however I style my hair. I tend to curl it if I’m wearing it down as I find the hat and fascinators stay put better than when it’s straight and sleek.
I also always have a few extra bobby pins and safety pins in my purse in case the elastic on the fascinator breaks or I need a few more pins to make it feel secure. If it’s really not feeling secure, you can also find pretty hat pins for both fashion and function.
Where’s the best place to shop for Kentucky Derby hats for women
Start by searching for stores in your area and if there’s nothing locally have a look online. I personally like Etsy for finding some beautiful designs and supporting small businesses. There’s also Amazon if you’re wanting something inexpensive.
If you’re wanting to go all out with your Derby horse racing hat, research Milliners and have a look at Jenny Pfanenstiel designs. She was named the featured Milliner for the 146th, 147th, 148th and 149th Kentucky Derby and offers both ready to wear and custom designs.
Other things to consider when shopping for hats for the Kentucky Derby
When going hat shopping or trying them on try to avoid wearing makeup at least on your forehead so that you don’t mark the hats. Otherwise be sure to take a tissue with you that you can place across your forehead when you’re trying them on to avoid transference.
I tend to avoid wearing makeup on my forehead on race day too and just use SPF. Especially if I’m wearing a white hat which I tend to end up doing more often than not.
Massive Kentucky Derby hat haul
I got left high and dry by an Etsy seller so had to do some last minute Amazon shopping which actually turned up a lot of fabulous options. Here’s the best and worst of them, some hat shopping and styling tips and my final pick.
The fascinators in my video try-on haul in order shown:
- White felt fascinator.
- White fascinator with butterflies.
- Pink and pearl fascinator.
- White and pearl fascinator.
- White feather fascinator with net.
- White feather and crystal detail fascinator.
- White fascinator that was hard to place.
- Blue butterfly fascinator.
- Beige material flower.
- White net fascinator.
- Cream flower fascinator I held.
- Large white fascinator.
- Blue and pink flower fascinator.
Shop the best Kentucky Derby hats and fascinators
From designer to affordable Amazon finds for under $15, these are the most stunning styles I came across. There’s a shape and color for everyone and every outfit. As noted in the video above, you get what you pay for more often than not and some of the cheaper ones feel cheap but look cute.
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