The Paddock is fun.

It’s also super crowded along with being a bit wild. It’s kind of like a dressier, mildly more mature infield. But if you want to meet all kinds of people and your fair share of Derby characters, it’s the place to be. You can also usually spot a few famous faces as they make their way through or the ones that enjoy coming down and betting in the midst of it all (I once saw Jerry O’Connell this way – just randomly in line at a betting window in the middle of the madness).

When it comes to dressing for the Paddock, you want to embrace the spirit but you may not want to go all out, size-wise, when it comes to your hat or fascinator. Since it can get crowded down there, there’s going to be a lot of close talking and getting bumped into. This can make trying to peer out from under a wide brim a little difficult.

Jill Courtemanche ‘Fabiola’ Fascinator 
Vineyard Vines Seersucker Stripe Block Dress (under $150) 

This pretty, polka-dot pastel piece from Jill Courtemanche paired with this super lightweight seersucker shift from Vineyard Vines is the perfect way to look the Derby part without all the fuss. You all know I’m a sucker for a polka-dot so I absolutely love this piece. The minty-pastel color is a little more unexpected too and would be perfect with any pastel dress. Don’t forget that you can save 15% on any of Jill’s pieces through April 23rd (so you have it in time for Derby!) with the code LouWhatWear. 

Images by Tabitha Booth

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