Three Kentucky Derby Looks: Win, Place, Show

Events / Travel

With the Kentucky Derby only seven days away there might still be a few of you out there scrambling around to find the perfect outfit- one that says “Talk Derby to Me” without breaking the bank. Whether you’ll be gracing historic Churchill Downs with your presence or enjoying the “greatest two minutes in sports” at your own Derby party, here are my Win, Place and Show looks for the 140th Running of the Kentucky Derby!

Show: I love these fun Sam Edleman Horse Head Studs, Alice & You navy dress and Jack Rogers sandals to balance out this lively Nordstrom Butterfly Derby hat. Add a pop of color with a fun clutch and you’re outfit is complete. This look is cute, comfortable and perfect for spending your day around the paddock or at your local watch party. Get this look for $350 and spend the rest of your "Derby fashion fund" on mint juleps and betting the ponies.

Derby Casual

Place: While most people wear pink on the Friday before for the Kentucky Oaks, I absolutely love this Vineyard Vines Rose Print Dress for Derby day – it’s fun, feminine and part of their Kentucky Derby collection. Pair it with a gorgeous John Lewis Hanna hat in lipstick pink, Longchamp Besace Derby bag (how gorgeous is this?!), an Alex and Ani horseshoe bangle (or three because they are fantastic to stack and even have a Derby line) and your favorite wedges for a chic outfit. It’ll run you about $700 dollars (plus shoes) and the best part is that the hat, bracelet and bag are super easy to pair with hundreds of other outfits – perfect for a day at the races or a day at the office!

Vineyard Vines Derby Look 

Win: If you’re looking for something more upscale to wear while spending your day in Millionaire’s Row or just because you want to look, and feel, like a million bucks, look no further. I love the idea of pairing this whimsical Arturo Rios black couture fascinator (complete with the gorgeous veil) with a dainty coral Forever Unique Mina Lace Dress (also available in black), simple Italian-made, snake leather, nude 'Foxglove' Kurt Geiger heels and fun gold box clutch. Finish off the look with a bold red lip and ta-dah, Derby perfection. Priced around $1,000.

Derby Red

Don’t forget to post pictures of your Derby best on Instagram and use the hashtag #AmericasBestFashion, your picture could show up right here on our site!

I’ll be celebrating the Kentucky Derby at our official NYC Derby Party - The Brooklyn Derby. Where will you be?

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