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.

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