Let’s be honest: you’re more likely to think of those memorable hats than be able to recall the name of the winning horse from last year’s Kentucky Derby. Of course the Kentucky Derby is more than just a world-class horse race, it’s one of the greatest people-watching and head-turning events in the world. Headwear options for the actual derby and all those watch parties are practically unlimited, as long as you can wear it with confidence! Once you’ve decided upon the most stylish and eccentric hat you can find, round up your friends, tune in, and savor the supposed good luck that comes with your headpiece. Here are five hats we like that won’t break the bank – use your remaining funds to bet on that winning horse!
SAKS OFF FIFTH | COLOR-BLOCK HAT | $59.99 |
Combining a slimmer brim with a decorative bow on top of a neutral pattern, slip this hat on with any outfit of your choice. It’s certainly not the most outlandish hat to be seen at a derby party, but will likely serve you for years to come.
SAKS OFF FIFTH | LARGE DOWN BRIM FLOPPY HAT | $29.99 |
The idyllic and iconic Southern-style hat: it is stylish, breathable, and floppy. Wear this at the perfect angle to start the day, but know that however it ends up after the race it still looks good. As a bonus, you can head to your local craft store to spruce it up with some floral and make it one-of-a-kind.
T.J. MAXX | STRAW BUCKET SOLID CROWN HAT | $12.00 |
Reminiscent of the cloche hats so popular through the roaring’20s, why not purchase a hat that could serve you well more than once this Spring: a derby day event and a royal wedding watch party! Use its simplicity and elegance to pair with a beautiful, floral-patterned dress.

T.J. MAXX | FANCY PARTY HAT WITH FLOWER | $19.99 |
With the flat and stout brim, you have the option to wear this as you please, whether it be high or low on your head. But there’s no getting around it – this will be a showstopper once derby day rolls around.

SAKS OFF FIFTH | GROMMET TAUPE SUN VISOR | $16.99 |
Who said a hat had to be closed on top? Use this visor to let some breeze through you hair while simultaneously stick with the style of the derby. This hat goes best with a hot, muggy afternoon and a big glass of iced sweet tea.
We’re placing our bets on you this year to wear the most stylish hats for the 144th anniversary of the Kentucky Derby. Just because you’re not there doesn’t mean you can’t celebrate. Based on only five hats of the many available at Tanger, we know you’ll find something to look your best in.