Heiji says: “This dress was inspired by Helen Frankenthaler, the abstract expressionist painter, especially in the red stretchy fabric on top. It looks like a long brushstroke.”

Styling tip: With a dress that has so much going on, keep the jewelry simple: “A necklace would detract from the collarbone, which is exposed so beautifully.”

Proenza Schouler flocked viscose crepe dress, $3,475, Ikram, 15 E. Huron St. Graziela 14-karat rose gold and diamond ear cuffs, $3,350, grazielagems.com.

Heiji says: “I love the play on a traditional ski sweater using sequins. It’s glamorous yet cozy—perfect for winter in Chicago.”

Styling tip: Ankle boots work well with a look like this: “The stripe adds to the sporty vibe.”

Dior silk and sequin dress, $47,000, Blake, 212 W. Chicago Ave. Loewe calfskin boots, $990, Ikram. Dior brass and crystal rings, $580 each, Blake.

Heiji says: “This may look like a coat, but it’s a dress with a forgiving silhouette that looks good on everyone. And the graphic design really pops.”

Styling tip: Consider wearing a dress like this open, with a formfitting top and slim pant underneath.

Loewe silk dress, $2,850, and Jolie Altman rubber, copper, glass, sapphire, brass, and diamond necklace, $1,815, Ikram.Christian Dior brass, crystal, and pearl ring, $770, Blake. Graziela 18-karat white gold and diamond ring, $2,550, grazielagems.com.

Heiji says: “Everyone should own a great black turtleneck. This one has the exact right cut, fabric fineness, and height. It’s actually a mock turtle—no fabric folds at the neck—which can be hard to find.”

Styling tip: Use the sweater’s simplicity to tame a flamboyant skirt.

Wool turtleneck, $1,145, silk taffeta skirt, $2,570, and rope and wood necklace, $1,385, Lanvin, 116 E. Oak St. Chloe Gosselin suede and snakeskin sandals, $750, chloegosselin.com. 18-karat yellow gold cuff, $9,100, and 18-karat white gold bracelet, $12,200, Sidney Garber, 118 E. Delaware Pl.

Heiji says: “I love Christopher Kane because he’s superexperimental—a total innovator with draping and how fabric falls on a woman’s body. This dress is not as revealing as you’d think: Other than the red chiffon, it’s actually quite substantial.”

Styling tip: Swap out the boots for stilettos and you’ve got a great evening look. Cold? Add a blazer.

Christopher Kane silk viscose dress, price upon request, and leather boots, $860, Blake. 18-karat gold necklace, $13,215, Sidney Garber.

Heiji says: “This print is beautiful, very artistic. I love the ladylike silhouette: The jacket is boxy, and the skirt is tulip shaped—superflattering. And because half of the jacket is shearling, it’s warm too.”

Styling tip: Don’t worry about adding a patterned shoe: “As long as you choose a neutral shade like this, an animal print can go with anything.”

Suno wool and mink intarsia jacket, $4,995, and cotton skirt, $450, sunony.com. Wes Gordon rayon lace blouse, $1,590, Neapolitan, 715 Elm St., Winnetka. Crystal necklace, $149, and rose-gold-plated and black crystal bangle, $169, Swarovski, 540 N. Michigan Ave. Calf hair pumps, $555, Stuart Weitzman, 520 N. Michigan Ave.

Heiji says: “This skirt is so painterly, and the subtle differences in fabric and pattern work together beautifully.”

Styling tip: Leave the blouse’s bow untied to echo the verticals in the skirt.

Wool sweater, $1,200, silk crepe shirt, $1,250, and wool skirt, $2,250, Bottega Veneta, 800 N. Michigan Ave. Python, crocodile, and suede heels, $2,600, Salvatore Ferragamo, 645 N. Michigan Ave. Brass and agate ring, $110, Mineralogy, 1944 W. Montrose Ave.

Heiji says: “These clothes have a summery look, but the fabrics are nicely heavy. For example, the skirt is constructed of wool panels with chiffon in between. The longer calf length is huge for fall.”

Styling tip: For the most flattering proportions, pair a midlength skirt with a substantial heel.

Dries Van Noten wool blend top, $955, Blake. Wool skirt, $6,995, Michael Kors, 900 N. Michigan Ave. DKNY suede sandals, $995, donnakaran.com. Unhada freshwater pearl necklace, $2,215, and Jolie Altman rubber, copper, and brass necklace, $440, Ikram.

Heiji says: “This fabric is so interesting. It’s not a heavy ’70s knit, but a printed wool and scuba material that has some lightness and stiffness to it. And I love the huge plexiglass flower brooch.”

Styling tip: Seek out short-sleeved tops that cover the biceps rather than bisect it: “This sweater has the ultimate flattering sleeve length.”

Cotton-blend vest, $2,550, skirt in the same material $740, cashmere sweater, $980, and plexiglass and crystal pin, $850, Prada, 30 E. Oak St. 18-karat gold bracelet, $16,575, Sidney Garber.

Heiji says: “We’re seeing lots of cropped jackets this season, and this one is a standout. The flower embroidery has such an iridescent shine, almost an otherworldly glow.”

Styling tip: “If you pair a cropped jacket with a longer shirt, any body type can wear it.”

Dries Van Noten polyester jacket, $1,030, and polyester pants, $610, Blake. Cotton shirt, $395, Michael Kors. Suede shoes, $1,150, Jimmy Choo, 63 E. Oak St. Deux Filles 18-karat rose gold and diamond earrings, $3,690, Ikram. Graziela 18-karat gold and diamond ring, $2,650, grazielagems.com.

Heiji says: “This coat is very special: It’s made of printed and quilted silk. And the voluminous pleated midi skirt is right on trend.”

Styling tip: Never pair a coat with a longer skirt without checking a full-length mirror: “A difference of two or three inches in the hems generally looks best.” Too revealing? Slip a cami underneath.

Silk and polyester coat, $5,200, wool skirt, $1,200, and patent leather heels, $740, Marc Jacobs, 11 E. Walton St. Unhada 18-karat gold, agate, and diamond earrings, $4,625.
Photographed at artist Theaster Gates’s newest project, the Stony Island Arts Bank (6760 S. Stony Island Ave.), which opens September 19. The derelict but architecturally significant 1923 building, which formerly housed a savings and loan, has been repurposed into a center for arts and culture.