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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Cynthia Rowley Liquefied Bouquet Tuxedo Jacket, $425, available at Cynthia Rowley. 810 West Armitage Avenue (between Halsted and Dayton streets); 773-528-6160.
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Gar-de Georgette Maxi Skirt, $288, available at TwentyThirtyFourty.
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Anya Hindmarch Beaded Straw Clutch, now $419, available at Scoop. 1009 North Rush Street (between Oak Street and Bellevue Place); 312-649-9880.
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Christopher Kane Women's Tank, $345, available at RSVP Gallery. 1753 North Damen Avenue (at West Willow Street); 773-770-6666.
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Chie Mihara Marta Wedges, $398, available at City Soles. 2001 West North Avenue (at North Milwaukee Avenue); 773-489-2001.
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Elise Bergman Harrison Blouse, $198, available at Elise Bergman. 2035 North Damen Avenue (between Dickens and McLean avenues); 312-952-7009.
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Marni Pants, $368, available at Rad and Refined. Contact email@example.com for showroom appointment.
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Cambridge Satchel Company 15-inch Satchel, $190, available at RSVP Gallery. 1753 North Damen Avenue (at West Willow Street); 773-770-6666.
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Gucci 2303 Sunglasses, $250, available at Sir & Madame. 938 North Damen Avenue (between Walton Street and August Boulevard); 773-489-6660.
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Holst + Lee Blazing Bonfire Necklace, $225, available at City Blue. 1444 North Wells Street (between North Avenue and Schiller Street); 312-664-2222.
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Gryphon Essaouira Tee, $249, available at Perchance. 11 East Walton Street (between State and Rush streets); 773-244-1300.
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House of Harlow Sage Shoulder Bag, $245, available at Rad and Refined. Contact firstname.lastname@example.org for showroom appointment.
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Dolce Vita Magg Wedges, $166, available at Lori's Shoes. 824 West Armitage Avenue (between Dayton and Halsted streets); 773-281-5655.
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Mara Hoffman V Wire Bandeau Print Bikini, $195, available at Intermix. 40 East Delaware Place (at North Rush Street); 312-640-2922.
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Matt Bernson Delphine II Sandals, $187, available at Perchance. 11 East Walton Street (between State and Rush streets); 773-244-1300.
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Sass & Bide Coming Back Shorts, $482, available at City Blue. 1444 North Wells Street (between North Avenue and Schiller Street); 312-664-2222.
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Vita Fede Capri 5 Wrap Leather Silver Bracelet, $175, available at Elements. 741 North Wells Street (between Chicago Avenue and Superior Street); 312-642-6574.
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ALC Megalie Dress, $372, available at Fix. 1101 West Fulton Street (at Aberdeen Street); 312-226-4565.