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1938

Mary Janes, Bringing Up Baby

High-waisted pants that actually let you breathe and those adorable Mary Janes somehow make the whole thing feel both tomboy and totally chic. Katharine Hepburn's relaxed elegance on the set of Bringing Up Baby.

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Modern

Jane Pumps - Mary Janes, shoes

Shop · $215

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Modern

Alameda Mary Jane Flat, shoes

Shop · $150

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Modern

Black leather ballet flats with V-cut and strap, shoes

Shop · $280

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Modern

J. Adams Honey Jane Heels for Women – Round Toe indented Pumps, shoes

Shop · $37.99

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Reproduction

LifeStride Women's Rozz Mary Jane Pumps, shoes

Shop · $47.99

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Reproduction

Heart Ruffle Lace Socks: Mary Jane Style Knit Ankle Socks

Etsy · $15

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Modern

Mcool Mary Womens Socks, Ruffle Turn-Cuff Casual Crew Socks

Amazon · $15

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Reproduction

1920s Mary Jane shoes - Black - Yvonne, shoes

Shop · $209

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Reproduction

1930s Premium Marlene Trousers - Almondine Lambswool

Shop · £174.12

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Modern

1930s Sailor Pants - Navy

Shop · £77.88

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Modern

1930s Marlene Trousers - charcoal twill

Shop · £95.37

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More looks by Katharine Hepburn

Black Velvet Promo Portrait

1938

Cyclamen Gown, Philadelphia Story

1940

Red Stripe Stage Cover

1939

Checkered Dress, Philadelphia Story

1940

Checkered Jacket, Woman of the Year

1942

Glamour Portrait, MGM

1941