Since there are so many different events going on in the infield at Churchill Downs during the Kentucky Derby, dressing for the event can range from formal to casual. I’ve put together three winning looks that will look great whether you’re at Churchill Downs or at a watch party!


Win: You can never go wrong with a timeless look for the Kentucky Derby. Designer Diane Von Furstenberg knows how to create classic dresses that make a woman feel beautiful, and this multi-colored woven twill dress is sure to turn heads at the races. The fun touches of the horse necklace and rose rings are a great compliment to the accent of gold that are on the orange pumps and large brim hat!

Want this look? Here’s where to find it! Diane Von Furstenberg Capereena degrada woven twill mini dress, net-a-porter.com; John Lewis Alexa Large Brim Occasion Hat, $235, JohnLewis.com; Gigi Hill ‘Natalie’ Handbag, $20, overstock.com; Lei VanKash Rose Pinky/Mid Ring, Boticca.com; Bee Charming Jewelry Wire Animal Necklace, $38, metroparkusa.com; Call it Springs Seveven Heels, $40, 6pm.com; Hannah Oversized Plastic Glam Sunglasses, 2bstores.com.


Place: The watercolor background on this H&M dress caught my eye and I thought it provided a great contrast from the black horses. I decided to work with that neutral color palette by adding the fascinator, earrings and clutch. As much as I love heels, you may be walking around a lot while in the infield, so those Victoria’s Secret flats may be the way to go!

Want this look? Here’s where to find it! Horse Dress, hm.com; J. Tomson Womens Trendy Short Sleeve Bolero Cardigan, $3.99, amazon.com; Chain Frame Peach Gem Drop Earrings, $8, Maurices.com; Jacques Vert Pink Floral Fascinator, $138, houseoffraser.co.uk; ASOS Envelope Purse with Metal Bar, $14, asos.com; Gianvito Ross High Horse Heel, wmagazine.com; Victoria’s Secret Pointed Toe Flat, $49, victoriassecret.com


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Show: I love this casual yet sophisticated look for spending the afternoon in the infield. The red cropped pants are sure to be a hit, and you’re sure to be comfortable in the Navy Collared Blouse. Alex and Ani bracelets are inexpensive and fun, make sure to visit their website for their Kentucky Derby-inspired line of energy bracelets. And can we talk about those Horse Wellies? What a conversation piece! You’re definitely in the money with this look!

Want this look? Here’s where to find it! Oasis Tipped Collar Blouse, $34, oasis-store.com; Gap Slim Cropped Pants – Rose Bush, $33, gap.com; Pure Edith Hat, $45, modcloth.com; Diane Von Furstenberg Limited Edition Chinese New Year Horse Envelope Clutch, $133, dvf.com; Gorjana Horse Stud Earrings, $35, shopbop.com; Alex and Ani Horse Saddle Expandable Wire Bangle, $32, bloomingdales.com; Joules Womens Wally Heritage Print Wellington Boots, psyche.co.uk; Vidonreta Gianna Wedge Espradrille Sandals, $67, lordandtaylor.com.

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Horses. Style. Living... from Saratoga to SoCal. Content Creator. Model. Vocalist.

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