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Fashion Crimes Podcast

Apr 21, 2023

The 2023 Kentucky Derby is upon us, and one super savvy Friend of the Podcast wrote us to ask Holly about what to wear to the Kentucky Derby. So, whether you are headed to the real Churchill Downs in Louisville, or just dressing up for your own party, Holly has “The Best Kentucky Derby Outfit Ideas” all lined up on this week’s episode. 


What makes up a Kentucky Derby Outfit anyway?


A long time ago, in a place far, far away, the derby started back in 1875 with the intention of a grand event to be luxurious and a place to be seen. It was envisioned for the “upper class,” modeled after British horse racing, where extravagant dress was expected. 


In that era, women of society wore large, elegant hats with matching gloves, shoes, dresses with corsets and or a very tight bustier. 

“A large, flamboyant hat was said to bring good luck.”

Men, of course, wore suits with ties, hats, and some wore gloves as well canes, etc. So even though fashion has changed throughout the decades, Derby clothing is still very spring-y, with colorful, embellished, and over-the-top fashion. An excuse to dress in your biggest, poofiest, dress and hat to match. #fabulousoverload


But the hat! The hat has been the number one staple of the Derby since it started. When it comes to a hat for the Derby, bigger is better. 


So, here is the short list of Holly’s Kentucky Derby Outfit Must Haves:


  • A fabulous dress.

  • Shoes, preferably platforms or wedges to be comfortable.

  • Oversized sunglasses.

  • A cute bag.

  • Jewelry. 

  • A Mint Julip.

  • If it’s hot, bring a portable fan.

  • Water, to drink.

  •  HAT or FASCINATOR! (non-negosh)

Start with your blank canvas, or the base of your outfit. (Holly is going to trademark that statement). 


In this case it might be the hat or the dress. The dress can be long or short (but it will be hot and mobbed with people if you actually go to the race, so dress accordingly.) 


Pick a color theme or pattern theme. (For extra fun as a couple, pick matching outfits or theme!)



See Holly’s Pinterest Board for this episode for her favorite dress styles.


Here are some of Holly favorite dress brands:




Platform and wedges give the illusion of a higher heel, but with a flat bottom for support all day and comfort. (AKA: smoke and mirrors).



Oversized sunglasses, statement jewelry and a fabulous handbag (to hide your fan and hold your water, because the weather will most likely be HOT!). 


The name of the game for Derby dressing is pattern, color and prints! This is your ticket to wear pattern, pattern and more pattern. Go big or go home! #youcandoit


For men, try a crazy printed suit – you know – the full suit with a pineapple pattern? How about a margarita pattern? See Opposuits for some hilarious ideas.



Any size and style of hat is up to you. Big floppy hats, stuffy stiff hats, gravity-defying fascinators: we love them all. So many to choose from!


Some Fave Brands for Hats:


Are you going to the Kentucky Derby – or throwing a Derby Party?  SEND US YOUR PICS!!! Send Holly a DM here.


Did you DM us this week with great comments and suggestions (WINK WINK, MELISSA)?  You’ll have to listen to see if Holly gave you a shout out!  


We love hearing from you – and we love featuring our fans – so please send email to or DM on IG


Thank you for being our Fashion Besties yet again this week! Please FOLLOW, LIKE, SHARE and REVIEW the Fashion Crimes Podcast and tell us what you love. 



“The Best Fashion Friend You Never Knew You Needed!”


Hosted by your favorite personal stylist and the only Holly you need to know, Holly Katz!