Start 2020 With a Wardrobe Do-Over

5. Black jeans. Faded blue jeans always look cool but black jeans give an edge to whatever else — without adding a black leather jacket. Black jeans always look dressier than blue ones yet they tone down any dress-up top, so you hit the dress-casual sweet spot looking like you tried. They make a quick tonal, monochromatic look possible with all our black tops and accessories without having to wear “real” black pants. All your black tees and sweaters will instantly have a new partner. Opt for a high-rise style with slim straight legs for a modern classic shape that's flattering to all.

Cate Blanchett, Charlayne Woodard, Mary Stuart Masterson, Marisa Tomei

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6. Wide-leg pants. If you love midi skirts, these are going to be your new basic. While slim pants will never die, trousers with a slouchy fit through the leg and waist-sitting high rise are making women happier and more comfortable than they've been in decades. Try a pair cropped just above the ankle bone for versatility with any shoe from flats to block heel booties, or get maximum swagger with a ground-skimming style (but know the extra length needs a higher heel or wedge to keep the line and legginess going). Extra-long looks good in photos, but stick to below the ankle bone and breaking on the shoe.

Rachel Zoe, Niecy Nash, Candace Bushnell, Wendy Malick

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7. A new pantsuit. The new relaxed pantsuit is anything but corporate — it goes from cool to polished with a few tweaks. Go for updated proportions like a slouchier longline jacket and pants with a cigarette or drapey leg that in no way resemble the boxy man-tailored versions of the ‘80s. Dress it down with a white tee and sneakers, make it edgy with a black turtleneck and booties, fun with a leopard blouse and wedges, dress-casual with a chambray shirt and suede loafers, trendy with mules and a message tee and, of course, sophisticated with a silk blouse and sling-back pumps. The color is up to you but I suggest pink or red for a gutsy look and white, gray or black for a more classic vibe.

Christie Brinkley, Eva Herzigova, Courtney Love, Madonna

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8. An updated trench coat. This is your perfect lightweight outer piece for nonstop style, rain or shine. It transitions between climates and pairs with anything from jeans to cocktail dresses. Look for structure that's not boxy or stuffy. A lightweight but generously sized trench layers easily over blazers and the chunkiest sweaters but is cinchable to show off a waist, too. Wear it knotted at the waist (do not buckle!) or open (tie the belt in back or slip into side pockets). A trench with a removable lining is pricier, but amps up the all-season appeal. No matter what you wear beneath (even your oldest jeans or leggings), you'll look fashionable, polished and cool as an ex-supermodel.

Regina King, Alyssa Milano, Mary J. Blige

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9. Hoop earrings. Studs are fine to sleep in. Now trade up to hoops — and the bigger and lighter the better. Thin round hoops in gold or silver in a medium to large size are classic but never boring and those studded with “diamonds” (fakes but super even for day) always rock. Once you get these basics, you'll be ready for next-level hoops with drop stones, heart and slightly geometric shapes.

Jennifer Aniston, Naomi Campbell, Uma Thurman, Salma Hayek

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10. A long, full skirt. What started as a trend is now a comfort and style basic. Wear a longer, wider skirt all summer with sandals, all winter with boots and never worry about crossing your legs or wearing pantyhose. The extra volume and swishy hem do camouflage bulges and pounds but the defined waist keeps you shapely. Just be sure to pair it with a tucked-in top. In the “midi” category, choose a length anywhere from a few inches below the knees to a couple of inches above the ankles, depending on your preference and style. The volume, length and shape make it a “star” piece that elevates other basics from ballet flats and tees to boots and a sweater. You won't regret it.