Spending a day at the race track is the perfect excuse to dress up and wear that huge, glamorous hat you’ve always dreamed about. Whether your style icon is Scarlett O’Hara or the Duchess of Cambridge, this guide will help you find the ultimate dress and hat combo, accessories, and a summer cocktail to get the festivities started. Not sure what you’re looking for? We’re here to help! We’ve narrowed down the best Derby Day styles to four categories with tons of accessory options to customize that final touch. No matter what, you’ll find a look that’s unique, stylish, and racetrack-ready here at Ever-Pretty.

Choose Your Look

Classic Glamour

For a timeless racetrack look, you can’t go wrong with a monochromatic outfit. Our favorites? A classic LBD with a bold lip color or a white lace dress with pastel accessories. Or, combine the two for with chic black-and-white patterns and accents like stripes or polka dots. Of course you can’t complete your look without a wide-brim hat in white or black. For a pop of color to this sophisticated look, try adding a bold lipstick (red for a classic touch, or hot pink if you want a modern edge), or even an accent to your hat like a feather or flower. If this look were a cocktail, it would be a Daiquiri!

Southern Belle

We all love feeling like the star of our own movie, so why not channel your inner Scarlett O’Hara for a dramatic and ultra-feminine Southern belle look? Try a floral fit and flare dress for a look that’s classic and romantic – and perfect for pastels. With bright colors and an airy, delicate feel, this look is perfect for spring. To keep with the garden-party vibe, pair this style with a wide-brimmed straw hat, embellished with flowers or an adorable bow that plays off of the colors in your dress. If this look were a cocktail, it would be a Mint Julep!  

Duchess for a Day

Who doesn’t want to feel like royalty? Channel your inner Kate Middleton for a look that’s sophisticated, classy, and elegant with a knee-length, solid-color dress with short or half sleeves. If you want to go full-on royal family, try a dress with a pleated skirt for an even more refined finish. The best part? You can pair your dress with an elegant fascinator in the same color to really feel and look like a fancy Duchess. If this look were a cocktail, it would be a Pimm’s Cup!

Fashion Forward

Tired of following the crowd? Turn heads by opting out of dresses and rocking a jumpsuit or romper instead on Derby Day! To keep your look fun and spring-ready, choose a bold color. Yellows and pinks are trending for this summer, so we suggest trying a jumpsuit in canary yellow, fuchsia, raspberry, or any hot pink or gold. And if you’re going to get creative with your outfit, why not do the same with your hat? Pair your romper with a bold organza, oversized floppy hat, or even a striking fascinator for an ultra-posh finish. Be the showstopper on Derby Day with this fun twist on the classic ensemble. If this look were a cocktail, it would be a Watermelon Margarita!

Derby Day Accessories

Accessorizing your look is crucial, and every detail matters. Obviously this is an outdoor event, so you want to be practical and comfortable while still accentuating your look. From eyewear to handbags, we have tips for every last detail so that you spend the day looking and feeling glamorous!


For sunglasses, don’t forget to choose a style that works best with your hat. For a chic fascinator, try some subtler cat-eye frames or a more rounded style, keeping with the feminine and eye-catching details of the hat. For wide-brim hats, don’t be afraid to go big and bold with your frames. Complete this look with oversized, Audrey Hepburn-esque round or square sunglasses for a dramatic and classy finish.


Since your hat will be drawing most of the attention, it’s important to keep your jewelry simple and understated as a complement. We suggest timeless pearls or daintier and more lightweight metallic pieces with no beading, jewels, or embellishments. Try a thin silver necklace with a cool-toned dress or gold with warmer florals. Going for the monochromatic look? A string of bright white pearls might be your best choice.


There’s nothing worse than being at an outdoor event with the wrong kind of shoes. Since you’ll be spending time on your feet and possibly even walking on surfaces like grass or stones, it’s important to stay away from stilettos to avoid a fall. Dainty ballet flats are an ideal choice since they’re both elegant and easy to walk in, but if you want to add some height to your look, wedged espadrilles are an ideal option. Or, try some strappy sandals for a flirty finish to your outfit.


If you’re spending all day at the racetrack, you’ll want to be able to carry your accessories without feeling like you’re lugging stuff around. We suggest bringing two bags – one larger bag for throwing in your sunscreen, sunglasses, a cardigan, or any other accessories, and a smaller clutch for a style statement with your outfit. That way, you can store whatever you don’t need in a larger bag set aside, and still have the essentials on you at all times in your clutch – essentially, have your cake and eat it too!


Don’t miss out on the opportunity to rock a stylish pair of opera glasses for a day at the racetrack. Get a front row seat for every furlong from any spot with a fun and sophisticated pair of binoculars. These are a must, in form and function – what other time do you get to use such an adorable and useful accessory?

Take a look at the full infographic here!