GAP Plaid Flannel Shirtdress

GAP's lovely Plaid Flannel Shirtdress ($50, on sale) gives shape and modern details, like side pockets and a sash, to an old, comfy standby. And unlike its nineties button-down predecessors, we bet you can get away with wearing this to your holiday dinner without evoking dirty looks and whispered demands to "change, NOW!" from your mom.

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