Bottega Veneta satin parka and matching cargo trousers, and Alexander McQueen Skull Mask sunglasses

Bottega Veneta satin parka, $3,500, and matching cargo trousers, $1,700, Bottega Veneta, 800 N. Michigan Ave. Alexander McQueen Skull Mask sunglasses, $455, alexandermcqueen.com.

Bottega Veneta satin parka and Alexander McQueen Skull Mask sunglasses

 

Mugler polyamide mesh bodysuit, Valentino Fairy Flowers crepe trousers, Nest Jewelry 22-karat gold-plated earrings, and hand-cut turquoise statement rings

Play With Prints

When mixing wildly different patterns, stick with the same palette.

Mugler polyamide mesh bodysuit, $850, Nordstrom, 55 E. Grand Ave. Valentino Fairy Flowers crepe trousers, $2,305, Ikram. Nest Jewelry 22-karat gold-plated earrings, $95, and hand-cut turquoise statement rings, $95 each, nestjewelry.com.

 

Gucci velvet jacket, stretch-velvet flared trousers, and Valentino silk blouse, Alexander McQueen brass ring, and Balenciaga Blade calfskin pumps

Mix It Up

Give a traditional menswear look a boy-meets-girl twist with feminine accents, like this bow-tie blouse and these pointed-toe pumps.

Gucci velvet jacket, $3,300, stretch-velvet flared trousers, $1,300, and Valentino silk blouse, $2,200, Ikram. Alexander McQueen brass ring, $360, Neiman Marcus, 737 N. Michigan Ave. Balenciaga Blade calfskin pumps, $975, Blake, 212 W. Chicago Ave.

 

Louis Vuitton Cosmic Motel polyester balloon dress, polyurethane flounce hem skirt, Silhouette ankle boots, leather gloves, and Elsa Peretti Bone cuff

Keep It Clean

Fashion-forward clothes work best with simple hair and makeup.

Louis Vuitton Cosmic Motel polyester balloon dress, $4,700, polyurethane flounce hem skirt, $2,080, and Silhouette ankle boots, $1,720, Louis Vuitton, 919 N. Michigan Ave. Leather gloves, $250, Ikram, 15 E. Huron St. Elsa Peretti Bone cuff, $700, Tiffany & Co., 730 N. Michigan Ave.

 

Sportmax cotton sweater and leather skirt, Histoire de Voir acetate and leather sunglasses, Studio SS earrings, Greta crew socks, and The Office of Angela Scott Ms. Jane leather oxfords

Always in Style

Punch up an investment piece like this classic leather skirt by pairing it with of-the-moment elements.

Sportmax cotton sweater, $425, and leather skirt, $1,150, Max Mara, 900 N. Michigan Ave. Histoire de Voir acetate and leather sunglasses, $475, Studio SS earrings, $325, and Greta crew socks, $19, Ikram. The Office of Angela Scott Ms. Jane leather oxfords, $695, theofficeofangelascott.com.

 

Dries Van Noten fringe coat, knit turtleneck, and Bottega Veneta viscose mule sandals

One and Done

Make a statement piece the hero of your look by pairing it with neutral basics like this black turtleneck.

Dries Van Noten fringe coat, $2,040, and knit turtleneck, $485, Blake. Bottega Veneta viscose mule sandals, $2,000, Bottega Veneta.

 

Versace La Greca monogram silk twill blouse, wool wrap miniskirt, and The Office of Angela Scott Ms. Presley derby shoes

Color Revival

Unexpected hues can give classic prints fresh life.

Versace La Greca monogram silk twill blouse, $1,275, and wool wrap miniskirt, $925, Nordstrom. The Office of Angela Scott Ms. Presley derby shoes, $525, theofficeofangelascott.com.

 

Balenciaga Artist Doodles satin dress, Editor paper calfskin bag, Nest Jewelry enamel mini huggie hoops, and Louis Vuitton Archlight technical satin and calf leather slingbacks

Less Is More

Keep accessories to a minimum when playing with daring makeup and patterns.

Balenciaga Artist Doodles satin dress, $3,550, and Editor paper calfskin bag, $3,050, Blake. Nest Jewelry enamel mini huggie hoops, $75, nestjewelry.com. Louis Vuitton Archlight technical satin and calf leather slingbacks, $1,030, Louis Vuitton.

Balenciaga Artist Doodles satin dress and Nest Jewelry enamel mini huggie hoops

 

Sacai cotton and polyester knit blouson, Hyke Pertex pants, Kat Maconie sandals, and Nest Jewelry hammered hoops

Two of a Kind

When pairing contrasting colors, make sure the hues are equally bold.

Sacai cotton and polyester knit blouson, $640, and Hyke Pertex pants, prices upon request, Ikram. Kat Maconie sandals, $380, katmaconie.com. Nest Jewelry hammered hoops, $95, Neiman Marcus.

 

Valentino virgin wool and silk blazer, matching cropped trousers, georgette blouse, and The Office of Angela Scott Miss Button polished leather midheels

Back to Basics

A classic shoe in a neutral hue grounds a vibrant-colored clothing choice.

Valentino virgin wool and silk blazer, $3,600, matching cropped trousers, $1,695, and georgette blouse, $1,690, Ikram. The Office of Angela Scott Miss Button polished leather midheels, $525, theofficeofangelascott.com.

 

Alexander McQueen cocoon-sleeve minidress, brass ear cuff, and brass crushed-chain ring

Alexander McQueen cocoon-sleeve minidress, $2,290, brass ear cuff, $590, and brass crushed-chain ring, $390, alexandermcqueen.com.

(Models) Christina Jones/Select Model Management; Jaelynn Hinton/Ford Models; (hair) Debbie Jacks/Distinct Artists; (makeup) Cammy Kelly/Distinct Artists; (stylist assistant) Hayley Koutsis; (painting) Kim Knoll