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Full Skirts
For the Derby, wear them with pretty tie-waist blouses or silk tanks. On other days, wear them in a more relaxed way, with a chambray button-down or slouchy gray t-shirt.
Sun Hats
Buy one you can actually wear again, like these. I'd totally wear the one on the left with a black bikini and feel very glamorous (and sun-protected!) on the beach.
Ladylike Bags
On Derby day, mix them in with equally feminine floral patterns and pastel pieces. On other days, use them to add a little color and personality to a sleek white dress.
Proper Sundresses
Armfuls of jewelry and spunky sandals might be your usual pairings during the summer, but for the Derby, keep it simple and traditional. And preppy. Think peals, lockets, ballet flats.
Retro Sunglasses
For the Derby, pair them with a classic red lipstick to complete the proper Southern lady look.
Prim Blouses
On Derby day, tuck those tops into a full skirt or toss that jacket over a simple sheath to give it more polish. Or, when not Derby-ing, you can wear alll three of these with distressed jeans and some cool stilettos.
Ballet Flats
Preppy and more comfortable than a pump. The ideal Derby shoe, with infinite real-life possibilities, too.
Classic Jewelry
If it looks like an heirloom (i.e. that locket), even better.
All spring (and summer), wear your gingham with simple sandals, white t-shirts, cutoff shorts—comfy downtime clothes. But for Derby day, wear them a little more polished.