Distilling Kentucky Derby Fashion: Classic Dress and Hat Tips

Jenna Bush Hager. Bless her heart.

It feels mean to list the myriad reasons why these two “Off to the Races” outfits chosen by Jenna Bush Hager for Southern Living are so, so, so wrong, from the inappropriate hats and the weird dresses right down to the to the uncomfortable shoes. Any Kentucky girl can take one glance at these and know that no part of them will work. But tearing them apart piece by piece seems cruel and petty, and the first rule of Derby is to be open, kind, and up for anything. So if Jenna Bush Hager wants to commit these Derby atrocities, I’m not going to judge her for it. Sometimes we have to learn our own lessons, and I’m sure Jenna Bush Hager would learn them firsthand if she ever came to a Derby (which she clearly has not). I do wish Southern Living would stop treating her as a Derby authority. Nobody knows how to do Derby like a Kentucky girl.

Derby projects and curriculum start in preschool. Believe us when we tell you, Southern Living, that nobody knows how to do Derby better than the people of Kentucky.

The Dress:

Distilling Derby fashion is relatively easy if you start with a classic sundress. The ideal piece has classic, flattering lines in a soft color. Derby weather can be unpredictable, so the perfect dress needs to be easily layered with a pretty cardigan on a cooler day, or a smart raincoat on a rainy day. These items can be easily shed if the sun comes out and the day warms up. A flattering dress in a pretty color that can be easily layered–it really is that simple. And, when it comes to a Derby dress, my philosophy is the simpler the better, because it is all about the hat.

The Hat:

There are so many hat options that shopping can feel overwhelming, which is why I like to start the process by finding the dress first. Of course, if you fall in love with a hat, you could easily work from the other direction. So many boutiques and trunk shows around town sell wonderful Derby hats and fascinators, and there are also hat designers in Louisville who do custom designs, like Kenzie Kapp or the Hat Girls.

I personally like to start with the dress and then make a trip to Dee’s Crafts, to get exactly what I want. Dee’s is a local craft store, but in early April they get all the millinery supplies you can imagine and you can smell the hot glue guns from the parking lot. They will consult with you and put your hat together for you, but I know what I like and prefer to do it myself.

I’m generally not a feather girl; I’m a flower girl, and I’m not sure about mixing the two on on hat. I’m not saying it can’t be done; I’m just saying you have to be careful with it. I like simple band of ribbon around the crown of the hat and tailored bow in a solid color behind the flowers. It is very, very, very easy to go over-the-top in a bad way at this point in the process, but you also have to be open to nontraditional millinery supplies. I always walk away from the actual millinery flowers to the silk flowers section, to see what creative options they might have in the right color scheme. I like a monochromatic pastel color scheme with a few pops of white or neutral, so I start with millinery flowers I like and then supplement with something in the right shade from the permanent flower department. I don’t generally do netting on hats, but I love them on fascinators.

A recent picture of my Dee’s shopping cart, which was obscenely filled with floral supplies for a Thurby fascinator and Derby hat.

Dee’s will put it all together for you and have it ready in a couple of days, but I’m good with a glue gun and I know exactly what I want, so this year I did it myself.

My hat, halfway through the creative process


The Shoes:

As for shoes, no one cares about them. You can’t see them in most pictures, and you’ll do so much walking that they’re probably going to get beat up anyway. They should be presentable and comfortable. I’ve worn the same pair of pink kitten heel pumps to Derby for the past ten years or so. They’re comfortable; they’re pretty; they match almost everything. I can walk long distances in them, and I don’t care if they get wet, muddy, or if someone spills bourbon on them.

The Takeaway:

Fashion is important at Derby, but you are looking at a long, exhausting day of walking, day drinking, walking some more, making random friends, and day drinking some more, so comfort is important, too. Go for dresses that offer layering options and shoes that don’t hurt. Add the perfect hat and you’re ready to go.

Kentucky Derby How-To: Ask A Kentuckian!

In Louisville, Derby is a birthright. We are born into it. The hats, the bourbon, the local events, the parties–these are ours from childhood. We all may do Derby a little differently–and there are lots of different ways to do Derby–but we can’t help knowing how it’s done because it is such a part of our collective identity. Getting away from it would be like trying to abdicate a noble title. You could do it if you wanted to, but why would you? Derby is who we are in Louisville; resistance to the Derby magic is futile.

We absolutely adore the bits and pieces of national attention we get during the weeks leading up to Derby. Kentuckians are very eager to show the world who we really are, and we enjoy having our most charming customs presented in a way that flatters us and our culture in front of outsiders. We are painfully aware that sometimes outsiders consider us to be ignorant, barefoot rubes with missing teeth and bad grammar. Sometimes there are embarrassing stories that don’t accurately represent us. It’s nice for others to see us portrayed as we see ourselves: hospitable, genteel people who can throw a good party, know when seersucker is appropriate, and can maintain a classy buzz for hours in a fabled historic setting.

You see, we are absolutely steeped in Derby traditions and Derby pride from infancy. As preschoolers we dress up in horse-themed outfits and homemade hats to march in school Derby parades. My children’s preschool devotes two full weeks to Derby-themed curriculum leading up to the big day; lessons cover all the big Derby Festival events like the Great Steamboat Race and Great Balloon Race. The kids do Derby Festival-themed crafts, and there’s a stick horse race in addition to the parade. By the time we’re in elementary school, we’ve all been to the Junior Jockey Club at Churchill Downs, have a working knowledge of the way betting works, and have personally met Churchill Charlie.

In Louisville, we know all the most famous horses’ names, and we consider them old friends who bring back memories of Derbies past. I remember having simulated Derby races on the swingset of my elementary school–we’d choose which racehorse we wanted to be, and whoever swung to the highest point the fastest was the winner of the swingset Derby. Everyone wanted to be Secretariat.

By the time we’re twelve, we know what type of bourbon is appropriate for bourbon balls, because we’ve already been making them with our grandmothers for five years, and we know what to do at the betting window, too. Most schools don’t even have school on Oaks Day, because it’s pointless; no one really learns or works during Derby time.

On Derby day, whether we’re in the infield, the Turf Club, a friend’s Derby party, or our own garden planting tomatoes, when the race comes on and they lead the horses into the gate and sing My Old Kentucky Home, most of us will get a little misty-eyed because of the beauty and pageantry of it all. In that moment, this place is presented to the whole world as wonderful. We already know that it is, but there’s something so moving about all of us joining together to sing the song together, and to celebrate our collective history and culture. It’s one we’re happy to share with visitors.

Derby is a part of who we are as Kentuckians, and we know how to do it better than anyone else. The parties, the dresses, the hats, the Derby Festival events are second nature to us, and we can tell you how to navigate it all, because we have lived it our whole lives. That should count for something, shouldn’t it? I wouldn’t go to Paris and tell the people there how to be more Parisian.

And yet, in recent years, respected magazines like Southern Living and Garden & Gun, have published stories and tips for Derby that are written by people from places like Texas, who couldn’t possibly have the knowledge or experience with Derby that every Louisvillian has gained just by a lifetime of Derby osmosis. I don’t understand this, because I know so many people who know Derby and are willing to share Derby. If you want to know about Derby, ask a person who has lived it year after year.

I’m not just talking about a one-time offense, either. Twice in recent years Southern Living has featured Jenna Bush Hager’s ideas about what to wear to the races, and, bless her heart, I’m sure she’s really sweet and lovely, but she’s the wrong person to ask about Derby. Ask me, ask my mother, my grandmother, ask any of my children, or any of my friends, but please don’t ask Jenna Bush Hager, because she has clearly never been to the Derby. Garden & Gun had a piece about how to throw a Derby party in recent years. It was written by an Austin-based blogger who suggested decorating with lilacs of all things. That is just blasphemy. Lilacs are lovely, but they don’t say Derby. Roses say Derby, and even the most inexperienced Derby novice knows that.

Southern Living and Garden & Gun are two wonderful publications; I read both of them and I enjoy the content and ideas presented. I love that they celebrate the South, and It pains me to mention their sacrosanct names in a negative light. It’s just that I don’t understand why they wouldn’t ask a Kentuckian about the Derby. It seems so simple. If you’re trying to decide what to wear to a rodeo: ask Jenna Bush Hager or an Austin-based blogger. If you’re trying to demystify Derby, ask a Kentuckian. You can ask one any of us.

If you’re going to the Derby and need to know how to navigate a day at Churchill Downs, ask a Kentuckian.

If you’re curious about attending one of the big fundraising galas leading up to the Derby, ask a Kentuckian.

If you’re going to Derby and need help with a dress, hat, and shoes that will look the part and last through a very long day of walking, drinking, and being exposed to various kinds of weather, ask a Kentuckian.

If you’d like to learn how to make the perfect mint julep, ask a Kentuckian.

If you’re looking for recommendations on bourbon or traditional Kentucky foods, ask a Kentuckian.

If you want to decorate your house for Derby, ask a Kentuckian.

If you’re throwing a Derby party in your town, and need to know how it’s really done, ask a Kentuckian.

We’re here and eager to help, and we know what we’re talking about.

I plan to break it all down for you in the next few days, so stay tuned.