Happy Friday friends! Coming in today with something a little more whimsical than normal but I guess I was inspired by my recent trip to South Carolina. Because seriously, how cute is this pineapple dress? Beyond Derby, it would make a great summer dress – poolside with flats, at a wedding with strappy heels, I mean I’d even wear it with sneakers for a casual party or festival.

Alice + Olivia Pineapple Clyde Shift Dress
Dolce Vita Effie Sandal | Kate Spade Byrdie Straw Crossbody 

But we’re talking Derby so let’s focus on the pairing above which I’ve thrown together for the Grandstand Terrace. This is a somewhat new area of the track, down closer to the third turn, that offers more amenities – like wagering booths, food and drink options, restrooms and additional seating – than the standard grandstand tickets. It’s kind of like the party deck of Churchill Downs. Also, as a side note, if you’re looking for more information on this area of the track, it’s not easy to find but here are some pictures. 

So for this area, I’m thinking you want something relatively simple (no elaborate necklines, weird straps, super tight fitting numbers) so that you can navigate the crowds – so this shift fits the bill (I seriously think about how quick you can get in and out of the bathrooms when picking dresses – it’s important). The print dresses it up a little while still being fun and youthful. I’d pair it with these block heel sandals (the heel isn’t too high and the block means you’ll still be able to walk in them by day’s end) and pack up this roomy crossbody bag. This Kate Spade one is big enough to slip a pair of flip-flops in, along with all your other Derby Day essentials. As for a hat, I’d go with a black feathery fascinator or a simple wide brim straw hat.

Just make sure not to spill a Lily on it so you can break it out all summer.