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Leather Vests Over Khaki Trenches
Polished and classic, never stuffy. (Until you need to go to a work meeting, and then you can just take the vest off.)
Printed Puffer Vests Under Boxy Parkas
Let that print peek out and you'll have the coolest utility jacket at brunch.
Black Fur Vests Over Black Coats

It'll make that simple black coat way more interesting.

Denim Vests Under Sweater Coats
Wear it with faded denim and wedge sneakers.