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Style a collarless jacket with a woven or pleated skirt and pair it with of-the-moment accessories like slingback pumps, a cord pendant necklace, and a suede handbag

Be totally Derby ready by packing a pen for jotting down your picks, an extra ponytail holder or bobby pins for windy day hair emergencies, toss in a couple bandaids in case of blisters and bring your lipstick for any touch ups

Source: Antique Sugar This 1940s pinafore seersucker blue and white dress by Betty Barclay is so adorable

Look closer, the neckline dips slightly into a soft V, framing things gently up front

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The first Sports Illustrated Swimsuit Issue (1964) featured Babette March in a white bikini on the cover