ANYI'S TIPS: What to Wear to the Kentucky Derby

The Kentucky Derby is known for its horses, sure. But the fashion, especially the hats, are just as entertaining as the races, or more so in our opinion. Putting together your Derby outfit can be a little intimidating (dress or hat, which comes first?). But it can also be a lot of fun. We've styled four very different Derby looks to inspire you featuring different sandals from our Spring Collection. If you've ever been to the Derby, then you know how much time you spend standing or walking around. No matter what you wear on your head, be sure you have something that you can stand in for five to eight hours on your feet. 

1–Classic & Feminine

The Kentucky Derby is the longest running sporting event in the United States, dating back to 1875, so you can't go wrong with very classic, southern style. Don't worry about having to perfectly match your hat and outfit. Here the black and white small print, and the black, tan, and tan colorblocking of the Bianka support the showpiece which is the hat. The dress is light and feminine and so is the hat, so they work together even if they're different color schemes. Imagine a black and white hat in its place or a red dress...not as interesting. 

The hat is the Asymmetrical Sinamay Hat with Flower from Nordstrom (great deal, btw). The dress is the Ivanka Trump Print Asymmetrical Popover Dress. The purse is vintage. The ring is from MadeWell

Shop the Bianka here


2–Whimsical & Youthful

Big, poofy hats not your style? There are plenty of great, more modern choices that still fit right in at the Derby. We fell in love with this hat from designer Eugenia Kim with its classic boater hat shape and typography elements. This hat had a very light, youthful feel so we paired it with an on-trend off-the-shoulder-dress and the platinum shimmer Linda sandals

The hat is the Eugenia Kim 'Brigitte' – 'A Rose is a Rose is a Rose' Hemp & Cotton Boater Hat. The dress is the Greylin 'Chantal' Off the shoulder Woven Swing Dress. The ring is from MadeWell

Shop the Linda here


3–Colorful & Bold

It may be tempting to find a single color dress and shoes to go with your statement hat, but it's possible to balance your outfit with various patterns and colors. With this look, we've combined a bold color and two bold patterns by pulling the pink color for the hat from the flowers on the dress and keeping the patterns very different but complementary–floral and stripes. The flower on the hat also ties things together as does the navy and ivory of the Maria sandal

The hat is the August Hat 'To the Races' Floral Downbrim. The dress is the Betsey Johnson Print Stretch Midi Dress. The bracelets are from MadeWell. The purse is vintage.

Shop the Maria here


4–Casual & Confident

If you're in the infield as opposed to the stands, you can still dress the part–just go for a more casual version. This ensemble centers around a lightweight, bohemian Alice + Olivia dress (remember, it can be hot in Kentucky that time of year) with a wide-brimmed straw hat and the ultra-comfortable sand suede Siena sandal

The dress is the Alice + Olivia 'Cari' Paisley Print dress. The bracelets are from MadeWell. The hat (similar) is from Nordstrom. 

Shop the Siena here. 

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