Within the seated sections of Churchill Downs, you will find hats of elegance and style. Generally speaking, women wear wide-brimmed, “Southern Belle” inspired Kentucky Derby hats. The hats can be decorated with flowers, feathers, bows and ribbons of any color to express creativity and individuality. Learn more about the Kentucky Derby Hat Tradition

Gain insight from our Derby Fashion Insider: Top 8 Derby Hat Questions Answered

Read below to learn more about Derby hats from our featured Milliners of the Kentucky Derby.   

Click Here for inspiration from Christine Moore, use promo code KYDERBYFEATURED147 for 15% off any of her hats. 

Talking Hats with Christine A. Moore

View Designs by Jenny Pfanenstiel   A donation of 12% of purchase will be made to the Churchill Downs Charity Foundation when website offer is mentioned.

Talking Hats with Jenny Pfanenstiel

Dress or Hat- Which Comes First?

You can exhale - there are two answers here!

Some will say that you absolutely get the outfit first. Then you design your hat to go with the outfit. (The argument here is that it's easier to custom design a hat than to "make" an outfit to go with a hat!)

Then there are those who say that you must definitely purchase, create or design your hat before picking out the outfit.

Most often in this case, matching the dress (or outfit) to your hat involves personal preference, however keep a few things in mind in getting dressed:

  • If your hat is having a pattern party, keep the dress design simple.
  • If the hat is simple and elegant, keep the outfit simple also for a classy look.
  • If you want a funky outfit, keep it consistent and accent the hat most of all!
  • If you have long hair, showcase a ponytail slightly to side or keep it down to one side to highlight the color on your face.

Hat or Fascinator?

A more recent trend in Kentucky Derby headwear is the fascinator. Smaller than a traditional hat and just as stylish, this piece of headwear has become more popular among Kentucky Derby attendees over recent years. Recently popularized by Kate Middleton, these chic, headpieces are made from a woven disc topped with feathers and netting and secured to your head via a comb or headband. They can be simpler to wear than a hat, and won't give you hat hair!

Do It Yourself-How to make a Fascinator

Inspiration from our Featured Milliners

Christine A. Moore 

Check out some of her designs below for inspiration or view her full line at at camhats.com.  Use promo code KYDERBYFEATURED147 for 15% off. 


Jenny Pfanenstiel 

Jenny is truly passionate about her craft and empowering the people who wear her hats to feel confident and beautiful. "It gives me great joy to see a client put on a hat I made them for the first time." Jenny doesn't just make hats though, she is able to connect with her clients on a personal level. She learns about who they are as a person, their likes and dislikes, do they like to blend into the crowd, or stand out and try new things. She creates an experience when they come into her hat shop. She will have the client try on different shapes and styles that complement their physique. They will then pick out the material and trims and in a few weeks’ time, will have a handmade hat made just for them. She sees a transformation in her clients when they first put on a hat that she made for them. They stand a little taller, they smile a little bigger, some even cry. She has had clients tell her that they felt invisible for many years and now when they wear her hats, they feel alive and beautiful and people notice them. This is why I do what I do. During the creation process, the hat becomes a blended creation representing both me and my client – making each truly special and one-of-a-kind.

Learn more about Jenny Pfanenstiel and view additional designs at www.formemillinery.com.