Outfit of the Week: Courtside Cool

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With the end of summer upon us, take a layering cue from Derek Lam's crew-neck top, the perfect piece to kick-start your transitional wear as you begin to plan a back-to-school wardrobe. Pair it with Givenchy's vermillion red Obsedia bag for contrast that brings occasion to J.Crew's denim shorts — notice how they're slightly longer, leaving more to the imagination than the ever-popular cutoff variety. Wear the look with a bit of blush for a flushed glow and solid wedge pumps, the better for maintaining height without losing leverage on city pavement.

Rayban Original Wayfarer Tortoise Sunglasses, $150 at Need Supply; Kate Spade White Padme Heel, $328 at Kate Spade; Bobbi Brown Pot Rouge for Lips and Cheeks, $25 at Sephora; J.Crew Denim Shorts in Patina, $79.50 at J.Crew; Givenchy Obsedia Bag, $1,555 at Forward by Elyse Walker; 10 Crosby by Derek Lam Long Sleeve Crew Neck Top, $345 at Moda Operandi; Madewell Square Hoop Earrings, $24 at Madewell.