Kentucky Derby Day Style

Kentucky Derby Style- Boston Chic Party

Kentucky Derby Style- Boston Chic Party

Happy Monday friends! Hope you had a great weekend!

It’s less than two weeks until the Kentucky Derby and the Summer Search Boston Kentucky Derby Party. This party is one of my favorite of the whole year in Boston and I can’t wait to don a big hat or fascinator for this year’s festivities. I’m thinking something pink 😉 ! Picking out your headwear for the Derby is such a fun shopping experience. The bigger, the better absolute applies. I rounded up some of the cutest Derby-ready hats and fascinators I’ve seen during my shopping to help you pick your favorite too!

What are your plans for the Kentucky Derby? I’d love to hear!

From top left, starting with top row:

Nordstrom August Hat Lilac Downbrim Hat

Old Navy Floppy Straw Sun Hat

ModCloth Something Special Tilt The End of Time Fascinator

Kate Spade New York Color Block Sun Hat

Nordstrom Aster Fascinator Headband

Nordstrom August Hat Poppy Cloche

Nordstrom Tasha Fabulous Floral Fascinator Headband

Nordstrom Sinamay Hat With Bow

August Hat Tulip Wide Brim Hat via Nordstrom

xoxo, Jenna


  1. April 21, 2015 / 2:48 pm

    I like hats and juleps, but I can’t watch the actual horse racing part. It’s so awful for many horses.
    I love fascinators and have an amazing designer in Ireland who is really great, if you ever need to have one made!

    • April 21, 2015 / 9:43 pm

      Oh Meghan the designer sounds amazing- I’d love to have a custom fascinator! Maybe for next year’s party 🙂

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