KY Derby Fashion: The great debate – hat first or dress?

This one’s jucy because it’s such a nuanced topic for us, ladies. A lot of thought, time, effort and money goes into creating an outfit for Derby.

In reality, though, IMHO and experience, the answer is: whichever one you find first that inspires you to wear it because it’s your budget. Sounds very similar to the answer I’d get when planning my wedding.

Some years I’ve found THE hat that I wanted to wear. Other years, I found THE dress first that I really liked and wanted to wear to the track.

If I can offer some advice from my experience: go to both days – Oaks & Derby – so that you get two chances to do it both ways. 😀

The year it was dress first

In 2023, we decided to treat ourselves to all-inclusive tickets to go to Oaks Day (the Friday before the Kentucky Derby). I had one day at the track to make an entire outfit count.

I ended up finding the dress first from Draper James. They even made this dress part of their Derby email campaign.

In fact, Elizabeth McCall, Master Distiller at Woodford Reserve is known to wear Draper James dresses.

It’s an absolutely lovely sun dress. Pockets. Perfectly tailored. Low maintenance being machine wash/tumble dry low (am I right, ladies?!).

The dress helped define and shape the direction of the type of hat/ fascinator I ended up having custom made by the talented hat designers at Anna’s Additions.

This is my first custom had I had made since moving to Louisville. I love it and wear it every chance I get.

Another scenario was planning my outfit for my sister-in-law’s wedding in Georgia. We knew we wanted to wear hats since it was outside in October but I, obviously, wanted to take care not to upstage the bride.

I picked out a blue floral Draper James dress and paired it with more of a low key fascinator design from The Hat Doctor by Illana Kogan inspired by one I’d seen Kate Middleton, Princess of Wales, wear. Simple and elegant.

I love being able to wear one of my hats or fascinators to a wedding.

When you find the hat first

Being a local, I get the unique pleasure of getting to visit the local shops and boutiques after the Derby rush in May to see what remains on the shelves of the hat and fascinator inventory. In doing so, I picked up this beauty:

We were invited back to the track over Memorial Day weekend. A friend’s company has a corporate box at Churchill which was an incredible experience so, for our first time as a guest, I wanted to look very classic, polished and put together.

I purchased a few additional colorful feathers to add to this fascinator depending upon the colors of the outfit I wanted to pull out. For this one, I went with a classic black and white base and accented with royal blue feathers, jewelry (blue pearl earrings that were my moms) and a purse.

On another occasion, I attended a local fashion show where the Hat Doctor, was a vendor. I fell in love with one of her pieces – a light pink, champaign colored fascinator with gem embellishments. It’s the perfect neutral fascinator to have on hand. Rizzo liked it too 🙂

Of course, I wore it to the fanciest industry dinner I attended in Napa Valley…dinner at The Castello di Amorosa!

I’m one of those people who, when I see a piece I love and I can reasonably afford it, I get it. Sometimes things just speak to you; jewelry, shoes, purses, hats. Fashion is a personal statement and there’s no way to really describe it, sometimes you know it when you see it. It’s an expression of yourself, an image you want to project, or a piece you want to look at later and remember the special occasions where you wore it.

But if I had to choose…

I would probably go dress first because that’s step one for building a successful outfit to this bucket-list event and full day out. It is literally an all day affair, walking around Churchill Downs sipping mint juleps. You want to be comfortable and stylish.

Additional considerations

weather
footwear
style: brimmed hat or fascinator
cost
where your seats are located

I don’t know how long people from out of town plan their outfit ahead. Most ladies locally spend probably at least the month prior, if not sooner, sourcing their Derby look. As you get closer to the first Saturday in May, you’ll want to have options because…weather. The forecast can really be a factor in the Ohio Valley especially during the week of Derby where there are many opportunities for folks to be outside at the track.

I recommend packing along two portable rain ponchos; one for you and one for your hat. You’ll need it if the weather turns wet and windy.

Another factor is footwear. I went between finding a really cute chunky heel but come day-of, decided I’d be better off in a pair of white, Under Armour shoes. Boy, was that the best decision ever! We walked out of the grounds and over to the UofL stadium to get picked up by my brother at the end of the day. I don’t think I would have made it in anything else.

Seat location: over the years, Churchill has continued to invest in projects to upgrade or build out the stadium area and experiences around the racetrack. When we went to Oaks Day, our seats were closer to the track itself and were therefore benches, a few rows away from the track. We were mostly walking on a combination of uneven concrete, brick or stone. A tiny heel isn’t ideal for navigating the stadium area.

Inside the newer, First Turn building; it’s beautiful. The flooring is more like what you’d find in a large event space; like a shiny tile. In that case you could get away with wearing nicer shoes, maybe even a heel (there’s still a ton of walking).

If you’re up in one of the elevated boxes, there’s a combination of outdoor concrete patio and indoor carpeting. So it really changes depending upon where your seats & section are. Everyone is free to roam the grounds but you need a ticket to get to your seat especially if you’re at the rail.

In terms of budget, it’s expensive to attend the Derby, from tickets to transportation, let alone attending both days. I can appreciate that not everyone has an unlimited budget. Many of the milliners have pieces that are very expensive and can cost hundreds of dollars. I personally like to keep my pieces between $100- $350. Which is why I love working with Anna’s Additions; they work within your budget and design such beautiful pieces with the materials and assortment of feathers they have in their store. It feels really special to wear something that’s custom and truly unique.

I hope I don’t give off the impression that I own numerous Derby hats. As of writing this, I have four total (which my husband appreciates): my main Derby hat that’s a white brim with a yellow rose, and four fascinators ranging in color from white, blue and rose color. Though, I could use one in black. I try to pick out pieces that look timeless, are versatile and can be worn with other outfits at occasions where I want to dress up a bit more.

I do adore hats in general. A favorite brand I discovered in San Francisco is Goorin Brother’s, especially their fedoras, because they’re so well made and offer great sun protection whilst also being stylish.

Ok, back to the races. Lastly, do you go brimmed hat or fascinator? Here’s how I made my decision: since I knew I would be wearing a sundress where my skin was exposed, I chose to get a wider, brimmed hat made. I kept an eye on the weather and it ended up being a beautiful, sunny day. I was grateful to have a big hat to shade me and keep me effortlessly cool in that situation. No sunburn for me!

A fascinator would have only shaded one side of my face that day so, if you do absolutely plan to wear a fascinator on a sunny day, pack sunscreen in your purse and make sure it’s also built into your makeup because if you are on the ground level, or just walking around, you WILL get plenty of exposure to the sun.

In summary

It’s both. It’s either. It’s what speaks to you first.

The way I see it, everyone that gets the opportunity to come to the Kentucky Derby and participate in the pageantry of Oaks and Derby is fortunate to have to go through this process. It takes a LOT to pull together an outfit for an all-day outdoor event where everyone brings their style A-game, let alone plan for alternatives day-of come rain or shine.

What you wear to the track is only one part of the day. It’s also an incredible experience to witness the speed and power of the horses racing throughout the day.

It’s an experience unlike any other. You’ll see so many other beautifully dressed people. When you see someone owning their style, tell them!