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Utility Jackets With a Twist
Roomy enough to layer over bulky sweaters, a lighter-weight long coat makes an otherwise winter-ish outfit look fresh, especially if it has a fun print or color. I always start the season by buttoning mine up all the way and topping it with a beanie; by May, it's unzipped over a flimsy white T-shirt.
Bright Maxis
Long skirts are such an easy way to cheat; you can wear tights and boots beneath one and no one will see! Also, most any cold-weather knit works on top: long cardigans (with a belt, always), cropped pullovers (if the bottom is high-waisted) and slim crewnecks (just like Leelee Sobieski in this Dior dress) included.
Sheer Coral Lips
As pinky-orange gloss is matte red lipstick's sun-kissed sister, it instantly makes every look a little more beachy. Even if said look consists of wool pants and a puffer.
Washed Denim
White jeans have transitioned into year-round staples, so rely on light-wash denim for a more seasonal look instead. Even with boots and a blazer, these have the rumpled, fuss-free feeling of spring.
Pastel Shoes
Pair these with all the black trousers and dark-wash jeans you've got to wait a little longer to pack.