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Pastel Coat
Wear It Now: With a snug-fitting cotton minidress—very Edie Sedgwick. Wear It Later: Over a creamy turtleneck and wool pants—the latter in a complementary Easter hue, if you really want to go for it.
Dressed-Up Sweatshirt
Wear It Now: With a statement necklace and a kicky flounced skirt—the full-of-movement hemline will look awesome peeking out from beneath your boxy pullover. Wear It Later: With second-skin leather skinny pants, heeled booties and a beanie.
Winter White Turtleneck
Wear It Now: With a white slit-side miniskirt (or skort!) and cute booties, just like our September cover girl Blake Lively did. Wear It Later: With equally snowy trousers and a crisp white coat. Remember, you've got to go head-to-toe for maximum impact here.
Slip Dress
Wear It Now: Solo, of course! Just add some flat, strappy sandals and maybe a few dainty pieces of jewelry and you're all set. Wear It Later: Under a below-the-knee fur coat (real or faux!) for big-time boudoir appeal, or under an unbuttoned flannel and paired with biker boots for a total Saint Laurent vibe.
Plaid Blazer (or Coat!)
Wear It Now: With a short pleated skirt, à la Cher Horowitz. To keep the look from veering too '90s, swap out the chunky-heeled Mary Janes the Clueless heroine would've picked for some modern smoking slippers. Wear It Later: With thick tights, boots and a pencil or envelope skirt in a contrasting yet complementary plaid, just like the models at Céline's Fall 2013 show.
Silk Pajama Pants
Wear It Now: With a bow-neck sleeveless blouse in a print in a similar color palette, plus a cool exotic-feeling clutch. Wear It Later: With a sharp-shouldered blazer and pointy pumps, to lend those slouchy bottoms some shape.
Over-the-Knee Boots
Wear It Now: With a drapey t-shirt dress in an interesting (but not TOO crazy!) pattern or print. Wear It Later: With a cozy sweaterdress—make sure the hemline hits an inch or so above the top of the boots!—and a swingy bell-shaped coat. It'll make your legs look super svelte.
Leather Moto Jacket
Wear It Now: With a slouchy white tee, your favorite cutoffs and some beautifully battered high-tops. Wear It Later: Over a long-sleeved knit, pleated kilt-style skirt, thick tights and Chelsea boots to really play up the punk influence.
Full Midi Skirt
Wear It Now: With a midriff-revealing crop top and platform sandals. Wear It Later: With a luxe, tucked-in cashmere sweater and some Mad Men-esque kitten heels.
Knit Beanie
Wear It Now: With easy shorts (denim or leather!) and a kicky graphic tee. Very Cara Delevingne, no? Wear It Later: With skinny denim tucked into tall boots and a ladylike coat.