Summer School

What Mad Men's Sally Draper might wear her senior year: scholarly oxford collars, checkered skirts, and high-heeled loafers with attitude aplenty.
models
Txema Yeste
What Mad Men's Sally Draper might wear her senior year: scholarly oxford collars, checkered skirts, and high-heeled loafers with attitude aplenty.
models
Txema Yeste
1 of 18
Plaid Behavior

On left: Blazer, $1,850, dress, $895, Dsquared2; orange-collared shirt, $1,468, shoes, $936, Louis Vuitton; socks, $27, Falke; bag, price upon request, Salvatore Ferragamo. On right: Jacket, $3,830, top, $1,468, skirt, $1,995, Louis Vuitton; socks, $9, Foot Traffic; shoes, $895, Oscar de la Renta. On nails: OPI Nail Lacquer in Black Onyx.

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outfit
Richard Majchrzak/Studio D
2 of 18
Smartie Pants

Sweater, $450, Black Fleece by Brooks Brothers; brooksbrothers.com. Shirt, $29, Joe Fresh; (212) 764-1730. Skirt, $20, Worthington at JCPenney; jcp.com.

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shoe
Richard Majchrzak/Studio D
3 of 18
Smartie Pants
Shoes, $98, Vince Camuto; vincecamuto.com.
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model
Txema Yeste
4 of 18
Varsity Style
Jacket, $2,535, sweater, $865, skirt, $1,595, Stella McCartney; socks, $20, Etiquette Clothiers; shoes, $495, Vera Wang Lavender Label; sunglasses, $365, Oliver Peoples.
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bag
Richard Majchrzak/Studio D
5 of 18
Smartie Pants
Bag, $390, Raoul; raoul.com.
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model
Txema Yeste
6 of 18
Head of the Class
Jacket, $998, Rachel Roy; top, $720, skirt, $940, J.W. Anderson; socks, $12, Kate Spade; shoes, $895, Rochas; bag, $940, Marni; sunglasses, $340, Oliver Peoples. On hair: TRESemmé 24 Hour Body Non-Aerosol Hair Spray.
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socks
Richard Majchrzak/Studio D
7 of 18
Smartie Pants
Socks, $17, Lands' End Canvas; landsendcanvas.com.
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model
Txema Yeste
8 of 18
Study In Stripes
Jacket, $995, Jenni Kayne; white top, $580, pants, $580, Acne; black shirt, $1,065, Proenza Schouler; shoes, $1,130, Louis Vuitton.
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coat
Richard Majchrzak/Studio D
9 of 18
Smartie Pants
Coat, $795, 10 Crosby Derek Lam; barneys.com.
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shoe
Richard Majchrzak/Studio D
10 of 18
Smartie Pants
Shoes, $135, Ivanka Trump; zappos.com.
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models
Txema Yeste
11 of 18
Teacher's Pets
On left: Jacket, $895, Moschino Cheap and Chic; dress, $5,995, Calvin Klein; dickey, $140, Carven; eyeglasses, editor's own. On right: Coat, $4,995, dress, $6,995, Calvin Klein; top, $295, A.L.C.; socks, $250, Vera Wang.
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pants
Richard Majchrzak/Studio D
12 of 18
Smartie Pants
Pants, $68, Kensie; macys.com for stores for similar styles.
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sweater
Richard Majchrzak/Studio D
13 of 18
Smartie Pants
Sweater, $360, Camilla and Marc; shopbop.com. Shirt, $58, American Apparel; store.americanapparel.net.
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model
Txema Yeste
14 of 18
Gym Class Hero
Cardigan, $1,900, sweater, $480, skirt, $1,180, Jil Sander; shirt, $145, Lacoste; socks, $12, Happy Socks; shoes, $400, Stubbs + Wootton; sunglasses, $410, Paul Smith.
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glasses
Richard Majchrzak/Studio D
15 of 18
Smartie Pants
Eyeglasses, $340, Chanel Eyewear; (800) 550-0005.
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models
Txema Yeste
16 of 18
Sweater Set

On left: Jacket, price upon request, top, $695, Narciso Rodriguez; pants, $790, The Row; scarf, $98, J.Press. On right: Jacket, $1,180, Mulberry; top, $1,195, skirt, $730, Jason Wu; socks, $29, Falke. On eyes: Bobbi Brown Long-Wear Eye Pencil in Jet.

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blazer
Richard Majchrzak/Studio D
17 of 18
Smartie Pants
Blazer, $99.50, Calvin Klein Jeans; macys.com.
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model
Txema Yeste
18 of 18
Checked Out
Cape, sweater, shorts & tie, prices upon request, Salvatore Ferragamo; shirt, $395, Alexander Wang; shoes, $850, 3.1 Phillip Lim; socks, editor's own.
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