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Models: Sam Perry/Factor, Patrick/Chosen, Hair & Makeup: Lillian Sakamaki, Assistant: Sarah Crump

1 Work it Find a vintage item that could be tied to a current trend, such as these harem-esque pants.
Get it Vintage 1960s orange linen pants, $32 at Store B (1472 N Milwaukee Ave, 773-772-4296); multicolored tank, $38 at Sofia Vintage (72 E Oak St, 312-640-0878); studded mini vest, $37; three skinny jersey necklaces, $15 each; Melissa by Vivienne Westwood shoes, $150, all at Akira (locations around the city, shop.akirachicago.com).

2 Work it Make your basics pop with a bright vintage piece.
Get it Pink tank dress, $50; earrings by Steven Shein, $56; vintage striped dress, $26 all at Sofia Vintage; Alley black patent wedge, $130 at Akira; beaded knot necklace, $68 at Lenny & Me (1323 N Milwaukee Ave, 773-384-4300).

3 Work it Get creative with your vintage piece. You wouldn’t dare swim in this bikini bottom, but it works great as a pair of hot pants.
Get it Generation Love crystal tank, $169 at Sarca; vintage pattern blouse, $28; beaded pearl necklace, $15; crystal necklace, $38; vintage mod bikini bottom, $48, all at Dovetail (1452 W Chicago Ave, 312-243-3100); Poetic Licence shoes, $100 at Akira.

4 Work it Layering is key. This vest alone would be too costume-y.
Get it Vintage plaid shirt, $38 at Sofia Vintage; double-breasted vest, $34 ; umbrella, $36, both at Dovetail; Hudson jeans, $215; Spiewak & Sons jacket, $115; Android Homme loafers, $100, all at Akira.

5 Work it You can pull off wearing more than one vintage-looking item as long as you layer with newer pieces.
Get it Seneca Rising mesh tank, $102 at Sofia Vintage; vintage plaid bracelet, $60 at Sofia Vintage, sailor shorts, $30 at Akira; Eryn Brinie knit half-coat, $165 at Sarca (710 N Wabash Ave, 312-255-0900); red collar, $16 at Lenny & Me; Bowne Tatiana jewel clutch, $200 at Sarca; Jeffrey Campbell wedge shoes, $125 at Akira; vintage nautical scarf, $35 at Store B.

6 Work it If your vintage piece features a pattern, blend it with modern patterns.
Get it Harvard Yard seersucker pants, $190; vintage tie, $42; Harvard Yard blazer, $540, all at Sofia Vintage; Ben Sherman button-down shirt, $79; G-Star shoes, $127, both at Akira.

7 Work it The windbreaker is a summer essential, but sizes back then were a baggier, so you might have to get yours tailored to a modern fit.
Get it Vintage Dior windbreaker, $60 at Dovetail; Dorsia plaid shirt, $65; J. Lindeberg shorts, $120; Sebago dock shoes, $119, all at Akira.

8 Work it The scarf alone looks a little Rhoda, but adding the broach gives it a Carrie Bradshaw spin.
Get it Fuchsia silk dress by Lattice Panel, $245 at Sarca; vintage scarf headband, $18 at Dovetail; tropical bird broach, $20 at Akira; rectangular wooden bead necklace, $42 at Lenny & Me; Miss Me cork wedge shoes, $40 at Akira.

9 Work it Modernize an old-school frock with current accessories.
Get it Vintage cocktail dress, $86 at Lenny & Me; ring, $20 at Akira; rocker necklace, $75 at Sofia Vintage; Michael Antonio shoes, $45 at Akira.

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