Dressing Up Derby

Posted by on

The Kentucky Derby occurs the first Saturday of May each year at Churchill Downs in Louisville, Kentucky. What comes to mind when you think Derby? Probably horses and hats!

Millinery has been part of the Derby experience since 1875. It was modeled after the horse racing tradition in Europe, which was already well-established. Races were an opportunity for the social elite to be seen while wearing the latest fashions. In the 19th century, that meant women would order the finest gowns, hats, slippers, gloves and parasols from Paris. The fashion competition beneath the Twin Spires was almost as fierce as the competition on the track!


Milli Starr saucer hat Twin Spires Churchill Downs

 So how does one make the right fashion statement at the Derby in the 21st century?

1. Get inspired. Take a look at the racing fashion trends around the world. Royal Ascot releases an Official Style Guide each March. If you like the elegance of British style, also research the dress and millinery fashions worn by royals like Kate and Meghan. If you are more fashion forward, take a look at the most recent Melbourne Cup and Fashions on the Field competitions. Create a mood board.

2. Plan ahead. Don't wait until late April to start shopping. It will be more fun and less stressful if you aren't scrambling to find a suitable dress and fabulous fascinator at the last minute.

3. Find the perfect dress. Although I occasionally have clients who purchase the hat first, it's far more common to match the hat to the dress. Think Spring and Southern style. Cheery color and bold prints, even lace. A majority of my custom clients have been choosing beautiful blues including sky blue, royal, cobalt and navy.

The dress should reflect your own personal style, whether that's minimalist or avant garde, boho or belle. Unlike Royal Ascot, the Kentucky Derby has no formal dress code. You may wear strapless, spaghetti strap or halter top style dresses. It does not need to be "modest" though I urge you to pick a style that will be comfortable to stand, walk and sit in throughout the long day. I'm a big fan of The Pretty Dress Company (UK).


Derby Day style custom Milli Starr saucer hats 

4. Find the hat. This is where my expertise lies as I have worked with numerous Derby clients in my 22 years as a milliner. I highly recommend you find a professional milliner to work with as they can advise you on choosing the most flattering style and how to wear it. If my style doesn't resonate with yours or you prefer to work with someone local, they are now many milliners in the US. Contact the Milliners Guild or do a search on Etsy.

When shopping Etsy, please be aware that it is no longer a 100% handmade site. Many of the hats and fascinators listed are factory made in China. I no longer sell on Etsy because of all of the changes in corporate values and policy.


Green Boater Hat Kentucky Derby Royal Ascot 

Wide-brimmed hats will always be on trend at Churchill Downs but you will actually see a very broad range of styles (and price points). Straw is the most popular material as it's seasonally appropriate. The headwear trends for 2020 include pillbox hats, saucer hats, big bows, top hats, boaters and padded headbands or halo hats.

Many women opt for a custom hat or headpiece. The choice is sometimes driven by fashion, for example, the client wants to have a unique accessory that no one else has. Or the client may not be able to find something she loves among ready to wear designs. Other times, a client has to purchase a custom piece because she doesn’t wear the “average” size. That’s around a 22.5”-23” head circumference and a 12” ear-to-ear measurement.

The custom experience is truly a collaboration. I work closely with my clients to create a beautiful piece that complements their outfit and their personality.

The custom process does take weeks so if you are an instant gratification type of person (or if you waited until April and all of the talented milliners are fully booked) then go the ready to wear route. Find a local hat shop and try on lots of styles. Experiment in front of the mirror as most hats need to be angled to the right or left. Fascinators are also angled and perch over the forehead.

If you choose a fascinator, it should be worn over the part in your hair. In ready to wear, most fascinators are designed to be worn on the right side. It's one of those weird gendered fashion quirks, like shirt buttons being on the right (men) or left (women). For hats, it's the opposite ~ trims on men's hats are always on the left and women's are usually on the right side.

Please do not ask a milliner to copy another milliner's design. We're a fairly small community and respectful of each other. If you find a hat you absolutely love, then purchase it from the original designer. Or find someone to make a hat loosely inspired by the design. Imitation is NOT the sincerest form of flattery!


Derby Day High Style

5. Other accessories. To look polished and perfect at the races, you'll need to plan the outfit from hat to heel. I suggest comfortable shoes, perhaps a wedge or block heel instead of a stiletto. You may want to pack some flip flops or foldable slippers in your handbag for the trek back to the hotel at the end of the day.

A clutch or handbag can be a great way to add a pop of color to the outfit. Or tie accessories together around a classic dress. Just remember that the bag cannot measure more than 12” in any direction.

Keep the jewelry simple, especially if your millinery is bold. Pearl or diamond studs, small drop earrings. Simple necklace or bracelet. Don't overdo it when accessorizing. Remember the wise words of Coco Chanel (who began her career as a milliner!):

"Before you leave the house, look in the mirror and take one thing off.”


Updo with halo crown fascinator Derby Day hair inspo

6. Hair Style. Have a plan in place and pack everything you’ll need to style your hair on Derby Day. Depending on the hat, you may want to wear your hair down, in a low neat ponytail, or in an updo. Hairspray is an essential as it may be breezy at the track.


Rainy Day at Kentucky Derby

7. Inclement weather. Bring a shawl or jacket in case it's chilly. It has rained on Derby Day the past several years, so you may want to shop for a cute rain poncho to match your dress. I include a plastic hat cover with all of my custom orders but if you arrive in Louisville and realize you'll need one, they are usually for sale at the Kentucky Derby Museum gift shop, adjacent to Churchill Downs.

8. Traveling with a hat. I highly recommend using a sturdy hat box or hat case. A round hat box is included with each Milli Starr hat. Any box up to 18” in diameter can be your carry on item and will easily fit in the overhead compartment. Larger than that, I recommend shipping ahead to your hotel. Pack carefully in a hat box, inside of a cardboard shipping box. Always insure and get a signature upon delivery.


Kentucky Oaks butterfly fascinator

One final note about planning for Derby. It's a 2-day affair so double the fashion & fun! Most of my clients attend Oaks Day on Friday as well as Derby Day on Saturday. Kentucky Oaks is all about the fillies and pink! Wear pink on Friday to show your support for the fight against breast and ovarian cancer. A pink accent in one of your accessories is perfect. Don't dress head to toe in pink. You may want a fascinator for Friday and a brimmed hat for Saturday, mostly for ease of travel. If you can fit two pieces safely in one hat box, that's ideal. Keep all of my Derby Day tips in mind when shopping for Oaks. 💗

churchill downs custom millinery derby day derby style hats kentucky derby kentucky oaks millinery racing fashion spring racing style guide style tips what to wear

← Older Post Newer Post →


  • Beautifu and lovely female hats

    Kebby Nnyana on

Leave a comment

Please note, comments must be approved before they are published