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I love this publicity photo of actress Joan Bennett in a casual menswear inspired outfit, taking a cue from her contemporary Katharine Hepburn (they starred in Little Women together) and of course echoed by a more modern day Annie Hall. Can you believe this was back in 1938? The high-waisted flared pants are especially great--if you're looking for a pair, make sure they sweep the top of your foot even when wearing platforms.
Top: Topshop / Pants: ASOS / Belt: Zara / Lips: MAC Dark Side / Shoes: Rachel Comey / Necklace: The Vamoose / Sunglasses: Ralph Lauren
-- By Miss Moss
(Joan photo via Dr. Macro)