A V-back dress in liquid satin is seductive, but not racy. And it hits just above the knee (on those of us who are not six feet tall, that is).
To buy: Ports 1961 by Tia Cibani silk-satin dress, $595, ports1961.com. Tommy Hilfiger heels. Azaara earrings. Ben-Amun by Isaac Manevitz necklaces. Miriam Salat ring.
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Reach for a Classic Frame Handbag
While this top-handle shape is certainly having a moment, it’s never out of style. Partner it with a structured, good-quality coat and you’ll be able to use them both forever.
To buy: United Bamboo leather bag, $575, Creatures of Comfort, 323-655-7855. Sportmax coat in wool, mohair, and silk, $1,350, 212-674-1817. The Limited top. Anthropologie skirt. Talbots heels. Verdura pin. Miriam Salat ring.
3 of 10Melvin Sokolsky
Shine in a 1950s-Inspired Party Dress
The great thing about this stunning crinoline-boosted showstopper? While it celebrates sock hop–era style, the pixelated print transports it fully into the 21st century.
To buy: Callula Lillibelle silk dress, $495, SH Merrick, 540-832-0062. Pura Lopez heels. Bounkit necklace. Movado watch.
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Invest in a Versatile Sheath
Look for a shape that’s nice and structured, but with some feminine details, like the pretty bow on this one. That way, the dress can work for the office as well as for cocktail parties and weddings.
To buy: CH Carolina Herrera wool dress, $595, 516-365-5560. Pedro Garcia heels. Eugenia Kim hat. Verdura earrings. Ben-Amun by Isaac Manevitz ring. Tiffany & Co. wristwatch.
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Take the Circle Skirt for a Spin
Not every figure can pull off a pencil skirt or a mini. But thanks to its amazing lower-body camouflaging, a full skirt is beautiful on everyone. Just make sure to balance the look with a simple, close-fitting top.
To buy: Adam wool skirt, $395, 212-229-2838. Ann Taylor cashmere sweater, $128, 800-342-5266. Cole Haan heels. Verdura bracelet.
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Transition Into Fall With a Bold Cape
Whether you’re dressed in leggings, work trousers, or a cocktail dress, you’ll be able to throw on this striking boysenberry cape whenever it’s not chilly enough for a winter coat.
To buy: Coach wool cape with leather trim, $698, 866-262-2440 for stores. Calvin Klein skirt. J. Crew gloves. Monet earrings. R. J. Graziano bracelet.
7 of 10Melvin Sokolsky
Accessorize With a (Faux) Fur Scarf
Fur was the embodiment of glamour in previous eras, and now faux can be the same, thanks to its unreal (in a good way) softness and texture (no frizzy bristles here). Pair it with something dressy or a cozy casual sweater.
To buy: Uniqlo faux-fur neck wrap, $11, 877-486-4756. Tommy Hilfiger blouse. Talbots skirt. Bounkit earrings. Miriam Salat bracelet.
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Tie on a Bow Blouse
A billowy tie-neck top looks fresh, skims over curves, and feels as easy as your go-to button-down. (Make that easier, since there’s no gaping across the chest.)
To buy: Tibi cotton blouse, $220, 212-226-5852. Jones New York Collection pants (available in October). Talbots hat. Furla clutch. Charmco.com bracelet. R. J. Graziano brooch. Bounkit ring.
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Embrace Strategic Draping
True, the cut may seem formfitting, but the little center knot on this refined pick does a whole lot to conceal any hint of a pooch.
To buy: Magaschoni polyester-and-viscose dress, $388, K Renee, 515-453-8451. Furla scarf. LaCrasia gloves. Ben-Amun by Isaac Manevitz earrings. Gabrielle Sanchez necklace.
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Don’t Shy Away From Sparkle
“Why would I need a sequin bolero?” you ask. Imagine the possibilities: It goes with a black camisole and dark jeans for weekend nights out, transforms your same-old little black dress, and tops off nice pants for special (yet not too formal) occasions.
To buy: Chico’s jacket of rhinestones, sequins, and crystals (available mid-October), $199, chicos.com. Eileen Fisher top. Harvey Faircloth pants. R. J. Graziano brooch (on headband). Tiffany & Co. earrings.