Here are six practical and approachable looks as we head into the cooler days ahead. Fall outfit, winter outfit, fall shoes, winter shoes, scarf coat, sweater, square toe maryjane flats, satin pants, LTKShoeCrush LTKOver40 LTKStyleTip

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Chimi | Shopbop
Heaven Mayhem | Shopbop
The Max Square Mary Jane in Black Bouclé | Rothy's | Rothy's
Edie accordion bag in snake-embossed Italian leather | J. Crew US
Stratus pant in textured satin | J. Crew US
Cream | H&M (US + CA)
Contrast Trim Jacket With Matching Scarf | Commense