Stop putting it off. You know it's high time you did a full-on closet evaluation. Sure, you're stocked on all the beachy necessities (hello, giant pile of swimsuits!), but what about the other summer essentials? Every wardrobe needs those classic pieces—think power dresses, sky-high wedges, and a bright clutch—that will see you through more than just this season.

No sweat—we've combed the racks of our favorite Chicago boutiques to find the best of the best—and we do mean best. Behold, the most luxe investment pieces this side of Lake Michigan. Because—say it with us, now—you're worth it.

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