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The canal-lined city, which served as the backdrop for George and Amal Clooney's wedding in 2014, is known as a glamorous enclave for the rich and famous

Comfort Scale: At the end of each wearing day, we rated each shoe on a comfort scale of 1-10

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The 2026 Kentucky Derby Style Guide suggests Crayola colors, florals, skirt suits, and tactile texture on classic silhouettes. Two-strap heels, closed-toe wedges, and ruched loafers should also be a hit at the 152st Derby, though you might want to bring a backup pair of flip-flops in case of muddy conditions (or sore tootsies)