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.
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.
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.
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.
checked double breasted jacket, $129, zara.com; black pleated mini skirt, $64, topshop.com; "layla" foiled pencil skirt, $325, elizabeth and james, nordstrom.com
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.
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.
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.