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.
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.
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.
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.
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.
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.
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.
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.
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.
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, $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