Black Forest

Looking Back
Breathe new life into a vintage dress by ­donning super-high heels and colored gems with it. Balenciaga special-edition dress (1962 reissue), $3,990, and Prada suede ankle-strap shoes, $495, at Neiman Marcus; John Wind earrings, $72 at Joan Shepp; 18K-yellow-gold citrine and diamond ring, $2,200 at Robert Perlman Jewelry Designers.

Basics like a pleated taffeta skirt and lacy silk blouse will become your surefire fallback pieces for those last-minute invites.
Prada skirt, $1,335 at Neiman Marcus; Prada silk and lace blouse, $1,170 at Saks; skull and heart necklace, $336 at Third Street Habit.

Double Duty
A sexy sheer top paired with a cropped jacket and skinny gray jeans works overtime, taking you from day to night.
J Brand jeans, $166 at Knit Wit; Chloé silk sleeveless top, $1,035 at Neiman Marcus; Dolce & Gabbana wool cropped jacket with silk tie, $1,695 at Saks.

Make a statement in a look-at-me ballgown that carries all the class of your Favorite Black Dress.
Oscar de la Renta ballgown, $6,250 at Saks.

Low Tide
Black cashmere gets an update with a plunging neckline and elbow-length sleeves. Try it with ribbed cashmere leggings, gold chains and flat boots.
Autumn Cashmere sweater, $198 at Knit Wit; DKNY wool leggings, $148 at Joan Shepp.

Cinch a voluminous pleated skirt with a ­vintage-­inspired belt; ­finish it off with a fitted top and delicate chain.
Y’s by Yohji Yamamoto pleated skirt, $620 at Joan Shepp; Max Mara jersey tank, $195 at Bloomingdale’s; Pelle Melle belt, $122 at Gem’n’I; Oval necklace, $48 at Vagabond; Prada patent leather t-strap shoes, $490 at Neiman Marcus.

Natural High
Mix opaque leggings and killer patent leather boots with a simple shift for insta style cred.
Donna Karan lycra dress, $2,900, and Chanel patent boots, $795, at Saks; Wolford tights, $38 at Saks, Neiman Marcus and Joan Shepp.

Woman Overboard
The trench gets reinvented with tulle, brooches—and a hemline that screams for knee-high boots.
Chanel silk and tulle trench, $5,890, and Chanel brooches, $330-$340 each, at Neiman Marcus; Prada tall leather platform boots, $890 at Saks.