Monday, May 4, 2026

The Most Memorable Hats of the 2026 Kentucky Derby

I can't believe I actually missed the Kentucky Derby this year. Somehow I got busy and forgot - and ended up missing the most exciting Derby in years, with an incredible come-from-behind win in the final stretch! Not to mention missing my opportunity to drink a mint julep and wear a fabulous hat. 

Speaking of fabulous hats, there were certainly plenty of fabulous hats to be seen on Saturday. Some of them were wild and whimsical, and were beautiful and elegant. Let's take a look at some of the most memorable ones. 


The Wild and Whimsical

Diorama hats abounded, such as the matching hats worn by these two gentlemen, which portrayed Churchill Downs, where the Derby is run, as well as a leaping horse and rider, and of course, plenty of roses. 

This gentleman sported a horsehead hat with a jockey helmet and goggles perched on its head, and he accessorized with a cigar and a bow tie. 


This lady's hat was a giant pheasant made of red roses and various types of feathers. It's impressive that it's balanced in such a way that it stays on her head!


Another whimsical diorama featuring Churchill Downs, this hat also featured several American flags, a pair of hot air balloons, a large horse's head, and both red and white roses. 


This man earns extra points from me for both the charm of the red rose in his horse's mouth with a cardinal perched on it, but for dying his beard a vivid green to match the greenery on the hat. Now that's commitment. 
This jaunty cocktail hat featured a gold carousel with prancing horses dangling from its edges. 


Yet another diorama of Churchill Downs, but this one focused on the steeples and added various pictures and drawings on the underside. 

This rakishly tilted red pillbox hat featured an elaborate loop and black and red roses and a pair of red feather birds. Extra points for the fabulous dress and lips-shaped clutch. 

This delightfully oversized hat was edged and wrapped with a black-and-white feather boa and trimmed with purple ribbon, pearl beading, red feathers, and a red rose.

This rakishly tilted hat contained an entire garden, complete with moss and a butterfly!

 

Speaking of gardens, several ladies wore fascinators consisting of hugely oversized flowers in various colors. So fun!


The Beautiful and Elegant

This pair wore hats trimmed in long feathers in a mix of bright neon colors, coordinating nicely with their monochromatic dresses. 


This graceful yellow cartwheel hat was adorned with a simple long molded and looped yellow ribbon.


On the other end of the spectrum, this Gainsborough hat featured long, fluffy, pale pink feathers; long, narrow white feathers; and pheasant feathers; plus a pink, white, and navy bow topped with a navy cabbage rose.
This hat kept the majority of its decoration at the back, with a dense arrangement of purple and blue flowers and a few ostrich feather tips. 


This elaborately constructed black hat consisted of multiple strips that rolled up at one side to form a series of concentric curls. 

I loved this pert blue velvet pancake hat, which featured a burst of shorter feathers topped by three curled pheasant tail feathers. 


This whimsical light blue cocktail hat was formed of a large bow topped with a corkscrew of ribbon, accented with a pale pink flower. It reminded me of a wisp of smoke. 

But one of my favorites of the evening was this delicious vintage couple , who fit into both the whimsical and the elegant categories!