2. Old School by Vans
You shouldn’t need an explanation on why you need a pair of Vans in your closet as temperatures begin to drop, but just in case you do: The Vans Old School is a wardrobe staple for its simplicity and durability. This all-leather model specifically makes the look even better, because the shoe will acquire that gritty vintage look as you trudge through the winter.
As far as wearing them, just about anything goes with these (yes, even with suit pants, if done properly). ($70.00, vans.com)
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