Derby Days

So, true story… I’ve never been to anything derby related. A lot of Georgetown students go to the Foxfield races, but I’ve never been able to attend because of various scheduling conflicts.
I’m really excited, however, because this year, I was asked to be a guest judge at the Fourth Annual Kentucky Derby Party at the Iron Horse Taproom in DC. The event is benefitting the Perry Center. It’s going to be SO MUCH FUN! If you’re in the Washington, DC area, buy tickets and come!!! EEP!
(It’s on Cinco de Mayo, so I imagine that it will be extra fun!)
Since I am going to serve as the “fashion judge” (best outfit wins $100 bar tab), I thought I’d pull some cute cute cute looks. I also have to decide what I’m going to wear… 
I think that this dress is super flirty. You could probably even add a solid (maybe that turquoise green color) belt around the waist. I love Marley Lilly’s floppy hat selection. The simple one-color hat with the monogram is great and can be worn with tons of outfits. Wedges are also a great option to wear when you want height and are going to be outside. (Is there anything worse than sinking into the dirt/grass while wearing regular heels???)

Love the strapless dress– just don’t forget to sunscreen your shoulders if you’re going to be outside. The two-tone Marley Lilly hat complements the fun colors of the Lilly dress. Top off the outfit with monogrammed Jack Rogers and you’re ready for a day of fun.

Okay, the ruffles on this dress? To die for. Ruffles can be scary on dresses, but between the fitted top and defined waist the ruffles work for, not against the dress. I’m loving the bright yellow hat. And, the pastel boots means you can have fun without the sun.
Have you been to a horse race? What did you wear? Are you going to any derby parties?
PS Be sure to let me know in a comment or tweet if you’re coming to the event! I want to make sure we meet!

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I'm from Kentucky, and we take the Derby (and horseracing in general) very seriously. Going to races gives me the perfect opportunity to wear great floral dresses and socialize…happy to read that you're joining the fun!


I went to Carolina Cup a few years ago. I wore a 3/4 sleeve Lilly dress because it was a little chilly that year. I really like the looks you've put together, and they're just in time for the Queen's Cup that I'm going to this year!


I've been attending the Carolina Cup since I was 10 years old and while Lilly is always a winner, lately the cool kids are all wearing Laroque dresses. They will even custom make your cup dress so no one else will be wearing the same dress. Check it out (shoplaroque.com)!


I love seeing what people from outside of KY consider "Derby fashion" (which really varies depending on where at Churchill you are watching the race. Most folks don't know that.) Those are all so cute!! I'm going to Keeneland tomorrow morning and so wish I had the first one!!

Sara Grace

I'm so envious! You'll have a blast! I love the monogramed Jack Roger's & of course you can't go wrong with a monogramed sun hat! 🙂


That is prob going to be so much fun Carly! loving the lilly dresses (clearly!) Take a pic of your winner and post it here 🙂 i would love to see how they do it over there!! Went to the derby last year, sort of har to say hi to the horses with gucci stilettos, but it got done 🙂

love K


I'm going to Foxfield this year and I'm planning on rocking my Jack Rodgers with a floral Shoshanna dress I have from a few seasons ago (though I love that first Lilly dress!). I did get a killer sunburn on my shoulders last year, so I'm definitely planning on investing in a good floppy hat!