My (Yearly) Quest For The Perfect Kentucky Derby Hat & Dress

Plus Shoes, Purse & Accessories for Oaks Day #149

This is our third year in Louisville, Kentucky, and I feel like I’m just now starting to get the hang of the seasonal events. In particular, the first Saturday in May, is the Kentucky Derby. The “run for the roses” is preceded by two weeks of local festivities and events kicking off Derby season.

This year (2023), we needed something fun to look forward to and decided to splurge on all inclusive food & drinks tickets for Kentucky Oaks Day on Friday May 4th at Churchill Downs (the day before the 149th Derby). Fun fact, the actual “Derby” race itself the “most exciting two minutes in sports” yes, that race, actually takes place late in the day on Saturday (first post is10:30AM EST).

Run for the Roses

This year, May 6, 2023 the race post time set at approximately 6:45pm ET (3:45PM PT).

It’s a full day of seeing and being seen walking, sipping & cheering. Strap in, friends! You’d better be well heeled and hydrated for this all day affair. YOLO (You Only Live Once) πŸ™‚

Since Oaks Day is basically as close as we’ll get to the real thing, I thought it would be fun to document and share what I know getting my outfit together.

Where to buy a Kentucky Derby hat

Local Milliners & Boutiques in Louisville, KY

Here in town I’m gradually visiting the local milliners and boutiques and learning about the Derby tradition of haberdashery. I have a few tips for those shopping for a Derby hat for the event itself or a Derby themed party based on your situation.

If you’re in Louisville and want to shop in person…

I’ve visited three boutiques so far. Each is unique in its own way and the staff can help you find a gorgeous ready-made hat.

Tunies boutique: I was amazed at the square footage of the store; they had some Derby hats but also a large variety of clothing, shoes and accessories. Their featured milliner is Anna’s Additions. Her hat creations are, I think, quite reasonable starting at $190+ USD. Her shop is up the road at 8113 La Grange Rd, Ste 1 in the Lyndon Station Shopping Center.

The Hat Girls. Plan ahead to visit their shop: they’re open seasonally during the month of April. They have a beautiful variety of styles and colors (I wish this was my closet at home). The staff is very helpful and attentive. They’re a bit on the pricy side (most brim hats were $450+ USD) but, the quality and “statement piece” you acquire there will be well worth it.

Rodeo Drive Louisville. This is a really fun boutique to pop into and look around. Again, it’s on the pricy side but you can be sure to find at least one statement piece for any event you’re going to. Their featured milliner is Attitudes by Angie. Prices range from $600-$900 USD.

If you’d like your had made by a local milliner for delivery or pick up…

My favorite is The Hat Doctor. She’s one of the official milliners featured at the Kentucky Derby Museum. You can shop her beautiful creations on Etsy a her store. She ships her products. I believe The Hat Girls can deliver orders to local hotels and orders can be picked up at Anna’s Additions shop.

If you want to DIY and make your own

There are a few well known crafting stores locally from Michaels to JoAnne’s Fabrics. A friend got her hat (the base) and decorations at a place called Dee’s Louisville. That’s on my list to check out. Just make sure you have the crafting essentials like a hot glue gun (or old reliable: duct tape).

Local milliner magic

Anna’s Additions has hat bases and lots of decorations and feathers to help customize your hat. I thoroughly enjoyed working with the ladies at Anna’s shop. I brought in my dress and they helped customize my Derby hat that I wore to Oaks this year. It was so much fun. The store has everything you could possibly hope to balance on top of your head when creating a unique hat or fascinator. Here’s a glimpse of the creation.

On Oaks Day, I met another lovely lady who also happened to have her hat designed by the ladies Anna’s Additions. I came across the local coverage and a gorgeous photo of her. Simply stunning!

Adrianna Muster a wore a bright pink and green hat on Oaks Day at Churchill Downs in Louisville, Ky. on May 5, 2023.

How do you pick a hat for the Kentucky Derby?

I recommend a few things to consider:

  • What event(s) you’re going to (Derby, Oaks, another local event or Derby party themed event)
  • Whether you want a more fuller brim hat or a fascinator worn on the side at an angle.
  • If you already have your dress, what color and style hat might pair well with it.
  • If you’re buying your hat locally while in town leading up to the Derby, plan a list of boutiques and milliners to visit. There are also beautiful women’s and men’s hats sold at the Churchill Downs gift shop.
  • Your personal style; Derby time is about turning heads.
  • Consider your own appearance; what type of hat makes you radiant and confident? Try on a large hat brimming with feathers and color. As Marie Kondo would ask does it “spark joy?” If not, try on something more tame.
  • Classic styling tips: If you have a patterned dress, opt for a solid color hat. If you want a Derby hat that’s a statement piece, try to select a quieter dress or blazer that is a solid color or has a large pattern. Try everything on together before the big day to see how it’s coming together or what needs to be adjusted.
  • Start following a few hat makers on Instagram and save the styles you like so that you can point to what you’re looking for.

My personal style is classic, eye-catching, unique, tasteful and – on a practical level – one that can be worn again at fancy occasions (weddings, Easter or church services, graduations, tea parties etc.). This year, I’m looking to round out my current collection of hats to include a black brim hat that’s understated and versatile.

There are all kinds of options depending upon your style and budget. Now that we’re locals, we’re told the best day to go to actually be able to enjoy everything Churchill has to offer is Thursday (AKA “Thurby”) or Friday for Oaks. Fashion and style norms go out the window for Derby; anything goes. For Oaks Day, attendees are encouraged to incorporate pink to their outfit in support of women’s health issues in partnership with Norton Cancer Institute Breast Health Program.

Kentucky Derby hats for short hair

My hair is currently short. Both hats and fascinators work for short hair but they key is to think about styling. When thinking about how to wear your hair under a Derby hat or fascinator, use a styling moose or gel to hold short pieces in place like bangs. You can also use a hairnet or chignon to round up your short hair into a bun or use bobby pins to tuck it down. Short hair is also fun to style using a curling iron and pinning the curls in different ways to your head.

Depending upon how your hat or fascinator sits on your head, pulling your hair to the side and pinning it up or having a side ponytail is a polished look.

Try practicing a few different styles before the event so that you lock in your look.

Check out the fun hats I tried on recently on my Instagram Stories.

Why do ladies wear big hats to the Kentucky Derby?

Because it’s fun, it might be sunny (or raining) and hats compliment the spectacle of this event. I think the real question is, “how big do I go?”

My Fair Lady?

Or Titanic style?

The thing about the Derby is, go big or go home. In looking through photos from the 2023 Derby, I found this gem. Yup, somebody DID come decked out as Rose Dawson. Well done, Carrie Ketterman!

Fancy Hat Inspiration & Images

IRL, I’m a big fan of the hats worn by Catherine Princess of Wales. She always looks so polished and pulled together.

Two of my favorites worn with a side tilt are below.

This brown brim one with white flowers is subtle and tasteful too.

I’ve found a few styles on Etsy that I liked. This year, I’m looking for a black wide brim with neutral flowers and feathers. But, since I have a yellow patterned dress picked out, it’s looking more like I should opt for a lighter color brim. Especially if I can’t easily match the yellow of the dress to the hat like this…

The foundation: What I’m ultimately looking for and/or looking to create is a Kentucky Derby hat, wide brim black sinamay. I’d like a black brim hat to shade me from the sun. Hard part is that I like so many different color combinations.

Structure: I like the structure and flowers of these brim styles.

Getting warmer: This style brim in black (instead of navy or peach although very pretty!). Different style flower & bow on top.

This style of feathers in black and maybe the black orchids (instead of a large flower or bow).

Oooohh, this light yellow hat with purple orchids is not what I was originally thinking but it’s really pretty and eye catching. It’s making me reconsider black as the base and go with a light cream, white or yellow.

Pop quiz: What’s the difference between a Kentucky Derby hat, fascinator hat, tea party, wedding hat

Sometimes you see all of those search terms stuffed into an Amazon listing. I’m still learning but from what I can tell, Derby is the event to wear a statement piece hat or fascinator. A Derby hat can be as wild and creative or classy as the wearer desires.

Fascinators/fascinator hat is basically feathers & flowers on a headband (band can be thick or thin).

IMO, a Derby hat and fascinator can also be worn at a tea party or wedding. Be sure to use good judgement so as not to upstage the bride or host with your…hat. Here’s a great guide, “Top 8 Derby Hat Questions Answered.”

Completing the look: Kentucky Derby Dress, Shoes, Purse

I love a quality dress I can wear multiple times. That’s usually why I select something from Draper James. Reece Witherspoon’s line of clothing & accessories. Their dresses sell out fast online (practically anything she puts on sells. Get it, girl!). I saw the dress (below, right) on her website in May for $165 with a discount code and thought it would be fun for Derby so I purchased it. Now I’m working to pair it with my hat.

What to wear to the Kentucky Derby

Here’s what’s funny about life. I’ve already purchased my dress…then I get this marketing email from Draper James in early April.

Spoiler alert, it’s sold out.

For shoes, again, I go practical, because at Churchill downs you WILL BE WALKING all day and on all types of surfaces from asphalt, gravel, cement, carpet, to brick. People suggest packing along a pair of flip flops or flats but I usually prefer to invest in good quality, stylish walking shoes or riding boots.

This year, I pulled the trigger on buying my first pair of FREEBIRD mid-heel shoes. This style is the Dusty Rose color RANDI for $195. It helps when you shop their sales.

I’m slowly breaking these in but my thought is that they’re stylish, sturdy and comfortable enough to wear for an all-day event.

While reading and researching the event, I noticed in the what to wear to the Derby/Oaks page, it mentions packing along a pair of flats. Now, the Southern California girl in me immediately went to flip-flops, but that’s technically not the case. Even though flip-flops at any other time are considered inappropriate attire in terms of the dress code for Track Casual, all bets are off during Oaks and Derby (except for horse racing bets, of course!). I imagine because during those days, anywhere up to 150, 000 people can be in attendance.

That’s a lot of flippy floppies.

It’s always hard to balance fashion versus comfort but, I’m on a personal mission to try. I also purchased these flattering flats from Tom’s and I think they’ll fit nicely into my purse just in case my tootsies need a break.

Don’t forget a purse, dearie πŸ™‚

While researching purse and bag dimensions for Churchill Downs, I found this information dated 2014:

Purses or bags measuring more than 12 inches in any dimension will not be allowed through any admission gate;

But, it being 2023 Derby 149, I’m hoping for something more recent. Here is the page with security information for the week of Oaks and Derby (don’t take my word for it, always do your own research). Oh, here we go, this is relevant:


Churchill Downs Racetrack will enforce a restricted bag policy from Saturday, April 29th, 2023 through Derby Day (Saturday, May 6th, 2023). Each guest is permitted one bag no larger than 12″ x 6″ x 12″. 

For example, a clear, stadium size bag that size looks like this. Amazon sells one.

That (obvi) won’t be what I take to the track. I’ll opt for one of my more compact Dooney & Burke bags. A few options:

Pebble Grain Satchel

Small Lexington in the Spors section, comes in under the size requirements.

Belmar Janine 20 is a suitable size too. Boxy and fun.

Another great resource for stylish purses in a specific size is Kate Spade. There’s a local boutique in Louisville at the Simpsonville Outlets. The Staci Medium Satchel is a great option.

You guys. I found my hat πŸ˜›

Mint julep attached to a fascinator. #nailedit.

Pro Tip: Why you should pack along adhesive bandages instead of Band-Aid’s

I’ve heard some ladies recommend packing Band-Aids to Derby & Oaks to cover the blisters they get from walking around all day in their shoes. Here’s the thing–I cannot stress this enough–it’s a walking heavy event: get comfortable, cute walking shoes EARLY and break them in. Secondly, Band-Aid’s are for rookies.

Take it from me, a former competitive ballroom dancer who was dancing in 1.5″-2.5″ heels for practice sessions 3x’s a week and for 2 and a half minutes at a time for up to five times during competitions. I know a thing or two about how NOT to get blisters. I’m the non-blister queen.

Here’s my trick: Obviously, break in your shoes. And, use proper adhesive bandages for your feet and literally on your footwear.

Best adhesive bandage brands to use for blisters

Dr Scholl’s Blister Treatment

General brand adhesive bandages:

Band-Aid adhesive bandages – work much better than regular Band-Aid’s because they effectively cover the blister completely and don’t rub off as you walk throughout the day.

If you can, buy some moleskin and cut it into a few different sized pieces. This stuff is a lifesaver if you are going to be walking in sandals all day or hiking because it keeps any blisters you do develop due to shoe rubbing from being further aggravated or breaking open.

The best part about moleskin is that you can apply it to either your own skin or to the inside of any shoe to prevent further friction. See? As I’ve started to break in the shoes I will wear for Oaks Day, I’ve already identified a problem spot and applied the moleskin.

In closing, here’s your moleskin + adhesive bandage kit for Derby and/or Oaks day. Slip a few of these in your purse and you’ll never have to ask your date, husband, or group to slow down and carry you because your super cute shoes are giving you blisters. You’re welcome πŸ™‚

See you at the track! YOLO!

Retrospective on 2023 Oaks Day

Recapping the 149th Oaks and Derby, we lucked out on weather for Friday, Oaks Day. I made a game-day decision on shoes and I’m really glad I did. In breaking in the leather pumps I mentioned above, I got a fair share of blisters so on Oaks day, I opted instead to wear a pair of white “dress tennies” (tennis shoes). It was a great decision because at the end of the day, we ended up having to walk about half a mile to meet up with our ride share. Not ideal but that’s the reality of big events like this.

What I packed along in my purse:

  • ponchos I purchased on Amazon (in case of rain).
  • a plastic grocery bag (pro tip: to carry around the commemorative glassware we got to take home).
  • cash – faster at the betting windows and you don’t have to wait in line at the ATM.
  • sunscreen – it actually turned out to be a sunny day; my winter skin needed protection.
  • phone charger brick + connection cable – so helpful b/c you will be on your phone all day.
  • hand sanitizer & tissues – turned out to be very handy for eating the cheese fries and bbq pork sandwich.

Attendance: Churchill Downs announced that 106,381 people attended the Oaks, up more than 6% from last year’s attendance.

The game day decision of wearing Under Armour dress tennis shoes paid off for fashion, performance and comfort πŸ™‚ I danced my way across the “pink carpet” fashion show at Oaks Day. Hold my purse and queue the song “Can’t Stop The Feeling” by Justin Timberlake.

Oaks Day 2023 Fashion Highlights and your girl who can’t stop the feeling. Dance, dance, dance!

Additional article links

Oaks Day 2023 Fashion Highlights –

Derby Fashion: Neon colors, bold accessories and brightly colored hats stand out at 2023 Kentucky Derby “Derby Fashion Hats”

Town&Country “Here’s what to wear to the Kentucky Derby 2023” “The Difference Between the Kentucky Derby Hat and Fascinator”

Scenes from a Packed Oaks Day at Churchill Downs

As a (new-ish) local gal to the Louisville area, Holly is enjoying learning about and experiencing everything “living in Lou” has to offer. She and her husband explore local bourbon distilleries, restaurants, boutiques and Churchill Downs in their spare time.

* The posts on this blog represent Holly’s personal thoughts and experiences and in no way speaks on behalf of her employers. *