Classy Kentucky Derby dress, hat, and party ideas

The 140th Kentucky Derby is this weekend!
Now, it's a little strange that I'm mentioning this, because... I know very little about the Kentucky Derby and it's not something I've ever paid much attention to, but my office Fun Committee does an annual derby party complete with hat contest, fried chicken, mint juleps, and betting on the horses in the race (to benefit the local animal shelter).

I know so little about horses, or gambling, or Kentucky... but I do know how to get into a theme! I'm definitely excited for warmer weather and outdoor parties and chances to wear dresses, so you betcha I did my research this week and have been planning my ensemble (as you may have seen via Instagram last night).

I wasn't sure what color scheme to go with before I started researching. I thought maybe just red/white/blue? But turns out there is an official clothing brand of the Derby, Vineyard Vines, and their 2014 collection is all pink, navy, and white. Super preppy, playful, bright. I've done lots of red/white/blue holidays before, so this is something new! And hey, any holiday with pink in the official colors is fine by me!

Kentucky Derby dresses and hats


When I started my Pinterest research (the Fun Committee also sent out some suggestions for preppy wear), I saw lots and lots of BIG hats, little dresses, pastels, and heels. As you can probably imagine, these look very different on different people. Apparently the hats get pretty crazy at the Derby, and some people come with what look like pinata horse heads on their heads?? and the like... and some ladies look a little more Barbie and a little less classy American South. (The Kentucky Derby Museum has a nice piece about history of fashion at the Derby, here.)

I dug around, though, and found that you don't have to dress totally crazy to be on-theme. In fact, I'll probably pull out an old fave dress (I've made SO many preppy-colored dresses, lots of navy and pastels, that there are lots of options but it's hard to choose one for work. And one that will go with the big pink hat I borrowed from my mom's costume collection.). (I thought about dresses I have that would fit the mold, like this navy/white stripe dress (worn here) or my versatile white pique and eyelet dress (worn here), or my pale blue lace dress, or... hard to decide!)

In addition to the cheery, preppy dress, I'll need the following:

Kentucky Derby outfit essentials:

  • Big hat or fascinator 
  • Clutch 
  • Pearls or beads
  • Stripes or florals
Here are some lovely examples!
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Kentucky Derby drinks and party decor


Of course there are tons of party themes around the Derby, and some perfect food and drink. So, if you're looking to take on a party project this weekend, here are some ideas!!

I know the classic Kentucky Derby drink is a mint julep, but I'm not much of a drinker so I love the sound of this watermelon mint lemonade recipe, all from fresh ingredients.
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Hostess with the Mostest has a ton of Kentucky Derby party ideas and free printables for several themes - here.
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I even found some great DIY accessory ideas!

This DIY tissue paper fascinator is a great idea for a costume! Or, how about stripes + hat all in one? You could DIY this stripey bow hat with some very careful painting and a big ribbon.
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I totally would have made that fascinator had I had more time. I did this research at the 11th hour before the big party at work today!

Stay in touch on Instagram and Twitter - I hope to post updates!

Have you ever done anything special for the Kentucky Derby??

5 comments

  1. oh no! I almost forgot it was derby weekend! I love all the hats!

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  2. I've never done anything special for derby weekend, but I always love seeing all the people dressed up - why aren't there more events like this which give people an excuse for a themed dress up party??!

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  3. My friend who usually organizes a party is out of town this year, but I think I might just wear my giant hat around the house anyways. That watermelon mint lemonade recipe looks great. Perhaps I should plan a last minute party now that i"m thinking about it... Thanks for all the great ideas :)

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  4. Love the derby, as a kid we used to go to the race track by my hometown where they would show the derby on big screens and everyone would get dressed up. My boyfriend and I have gone to a few of the Derby parties in town here they are always fun.

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  5. I had forgotten about the derby too because of Cinco de Mayo! Time to break out the bourbon!! Beautiful post :)

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