Bottega Veneta satin parka, $3,500 and matching cargo pants, $1,700, Bottega Veneta, 800 N. Michigan Ave. Alexander McQueen Skull Mask Sunglasses, $455, alexandermcqueen.com.
Play with prints
When mixing very different patterns, stick with the same palette.
Mugler polyamide knit bodysuit, $850, Nordstrom, 55 E. Grand Ave. Valentino Fairy Flowers crepe pants, $2,305, Ikram. Nest Jewelry 22-karat gold-plated earrings, $95, and hand-cut turquoise rings, $95 each, nestjewelry.com.
To mix together
Give a traditional masculine look a boy-girl twist with feminine accents, like this bow-tie blouse and point-toe pumps.
Gucci velvet jacket, $3,300, stretch velvet flared pants, $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
Trendy clothes work best with a simple hairstyle and makeup.
Louis Vuitton Cosmic Motel polyester balloon dress, $4,700, polyurethane ruffled 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 fashion
Elevate an investment piece like this classic leather skirt by pairing it with on-trend 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. Angela Scott’s Office Mrs. Jane leather oxfords, $695, theofficeofangelascott.com.
one and done
Make an on-trend piece the hero of your look by pairing it with neutral staples like this black turtleneck.
Dries Van Noten fringe coat, $2,040, and knit turtleneck, $485, Blake. Bottega Veneta viscose mules, $2,000, Bottega Veneta.
Unexpected hues can breathe new life into classic prints.
Versace La Greca monogram silk twill blouse, $1,275, and wool wrap miniskirt, $925, Nordstrom. The Office of Angela Scott Mrs. Presley derby shoes, $525, theofficeofangelascott.com.
less is more
Keep accessories to a minimum when playing with bold makeup and patterns.
Balenciaga Artist Doodles satin dress, $3,550, and Editor calfskin bag, $3,050, Blake. Nest Jewelry Mini Enamel Huggie Hoops, $75, nestjewelry.com. Louis Vuitton Archlight pumps in technical satin and calfskin, $1,030, Louis Vuitton.
two of a kind
When pairing contrasting colors, make sure the hues are equally bold.
Sacai cotton-polyester knit jacket, $640, and Hyke Pertex pants, price 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 brightly colored clothing choice.
Valentino virgin wool and silk blazer, $3,600, matching cropped pants, $1,695 and georgette blouse, $1,690, Ikram. The Office of Angela Scott Miss Button Buffed Leather Pumps, $525, theofficeofangelascott.com.
Alexander McQueen cocoon sleeve mini dress, $2,290, brass ear cuff, $590 and brass crushed chain ring, $390, alexandermcqueen.com.
(Models) Christina Jones/Select Model Management; Jaelynn Hinton/Ford models; (hairstyle) Debbie Jacks/Separate Artists; (makeup) Cammy Kelly/Distinct Artists; (stylist assistant) Hayley Koutsis; (painting) Kim Knoll