you'll make your closet contents last forever

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You're all about a sweet deal. Online goods, sample sales, and second-hand stores are no match for you. But one sneaky-smart way to max-out your thriftiness is to spend your cash on goods that can really go the distance. Our deal du jour is a lot easier to master than you think. We're scouting maxi-dresses that will totally rock a street fair now, but will also keep you cute and covered when our lives return to chilly normalcy this fall. By shopping pieces that aren't so season-specific—and making sure you've got some finely tuned layering skills—you'll make your closet contents last forever. We know it's been awhile, and you might be a little rusty, so we're here to coach you through the best maxis to buy now, and the right pieces to pair with them later. Make sure your dollars get some serious, erm, length this fall.

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Acne Magical Ziggy washed-satin maxi dress, $540 at Net-A-Porter. AllSaints Spitalfields Kaito Leather Jacket, $495, available at AllSaints Spitalfields, 700 North Michigan Avenue (at Superior Street); 312-283-0400. Kate Spade Gold Rush Collar Necklace, $248, available at Kate Spade. Milly Paige Mini Bag, $265, available at Bloomingdales. Barbara Bui Lace-up wedge bootie, $398 (originally $795), available at Shop Savannahs. Alexander McQueen Embroidered Fingerless Gloves, $1,120, available at Alexander McQueen.

ONE by Heather maxi tee dress, $145, available at Shopbop. Tweed Blazer, $58, available at Need Supply Co. H&M Hat, $14.95, available at H&M. ASOS Triple Gusset Satchel, $51.72, available at ASOS. Mesa Necklace by Laura Lombardi, $115, available at Laura Lombardi Jewelry. ASOS ARIZONA Suede Lace Up Shearling Ankle Boot, $94.81, available at ASOS.

T by Alexander Wang CDC Sleeveless Shirt dress, $210, available at Opening Ceremony. Kara Ross Cityscape Cuff, gold with grey python, $395, available at Kara Ross. Day Birger et Mikkelsen long mohair cardigan, $315, available at Matches. Black Skinny Belt, $8.24, available at Dorothy Perkins. Leather Multi Strap Contrast Bag
$146.53, available at ASOS. ACNE Cypress Ankle Boots, $598, available at My Theresa.

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Topshop Mustard jersey maxi dress, $55, available at Topshop. Rachel Comey Shingle Boot, $449, available at La Garconne. VPL Cropped Dolman Sweater, $345, available at La Garconne. Mason Bracelet by Dannijo, $295, available at Dannijo. Pour La Victoire Bordeax Tote $299, available at Urban Outfitters.

Striped Linen Blend Maxi Dress, $17.80, available at Forever21. Shabbies Short Black Leather Boot, $415, available at Shop Savannah's. BB Dakota Hunter Leather Jacket, $300, available at Shopbop. American Rag Paige Backpack, $54, available at Macy's. Christine Pink Opal Rough Necklace, $65, available at Cities In Dust.