Best Bet: J.Crew Tipped Sweatshirt

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This cool-gray cotton sweatshirt, with a solid navy trim, is the perfect thing for an occasion that calls for something simultaneously casual and cool. Pair it with pointy-toed flats and relaxed denim for a comfortable and polished look. 

J.Crew Tipped Cotton-Jersey Sweatshirt, $70 at Net-a-Porter.