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Wear it over jeans, a tee & flats now, then layer it with long gloves, a scarf and high boots later.

You could wear the vest inside the jacket, too—but then again, why would you want to?

Choose a soft wool moto style instead of a stiff leather version: it looks just as badass, but layers so much better under winter coats.

Toss the vest over a summer-y sundress right now, then throw it back inside the parka once it hits tights weather.
Buy it a size bigger than you think. You can use the belt to cinch the silhouette over a dress now, because you'll want the extra armhole room to wear it over sweaters later.

Slim puffers are the best for layering under winter jackets, and this one has a sporty, collegiate vibe we'd proudly wear right now.

As a cropped jacket or drop waist coat, it's pleasantly off-kilter.