THE TWIST: This off-kilter jacket boasts supersize pockets set at an angle.
Hermès leather jacket, $16,300, and short-sleeved ribbed cashmere sweater, $3,375, Hermès, 25 E. Oak St.
THE TWIST: An accessory becomes the star with this whimsical take on a handbag, made to look like a camera. (Under the “lens” cap is a compact mirror.)
Chanel lambskin purse, $9,200, Chanel. Gucci crystal-embellished silk, cashmere, and mohair cropped polo sweater, $1,650, and Moschino cotton shorts, $555, Ikram. Exquisite J elastic belt with enameled buckle, $310, and Nest Jewelry 24-karat gold-plated brass and silver-tone bangles, $150 each, Neiman Marcus, 737 N. Michigan Ave. Fendi Roma stamped croc leather pumps, $930, fendi.com.
THE TWIST: A timeless menswear combination is rejuvenated with an oversize sweater and creeper shoes evoking ’80s punk.
Jil Sander oversize wool cardigan, $1,080, and lightweight wool cropped trousers, $950, Nordstrom. Loewe pinstriped cotton shirt, $1,150, Ikram. Jimmy Choo Marlow loafers, $850, Jimmy Choo.
THE TWIST: A sleeveless leather turtleneck bodysuit gets the ’90s treatment with padded shoulders.
Sportmax leather sleeveless turtleneck bodysuit, $425, Max Mara, 900 N. Michigan Ave. Chloé Italian leather A-line belted skirt, $3,450, Nordstrom.
THE TWIST: Business, meet casual. A classically tailored double-breasted jacket is paired with wide-legged trousers.
Officine Générale Kane wool double-breasted jacket, $835, wide-legged pants, $485, and Frame cotton T-shirt, $98, Nordstrom. Converse x Comme des Garçons Play canvas sneakers, $150, Bloomingdale’s, 900 N. Michigan Ave.
THE TWIST: A knitting needle that functions as a belt? Now that’s sharp.
Loewe cashmere cardigan, $2,100, cotton shorts, $1,600, and Campo leather mules, $1,200, loewe.com.
THE TWIST: Masculine, typically staid formalwear gets an enlivening makeover from jet beading.
Simone Rocha crystal-embellished wool sports coat, $1,800, and wool and polyester pants, $640, Ikram. Officine Générale cotton tuxedo shirt, $310, Nordstrom. Dr. Martens leather platform Chelsea boots, $210, Dr. Martens, 3452 N. Southport Ave.
THE TWIST: Crisscrossed straps elevate a tank top to high fashion, and blazing yellow modernizes the traditionally uptight three-piece suit.
On left: Hyke cotton double-shoulder tank, polyester midi skirt, and polyester and cotton corset belt, prices on request, hyke.jp. The Office of Angela Scott leather platform oxfords, $650, theofficeofangelascott.com.
On right: Dolce & Gabbana cotton and silk jacquard jacket, $3,945, cropped trousers, $1,325, and vest, $1,195, Ikram. Jimmy Choo Ixia 95 patent leather pumps, $895, Jimmy Choo.
Models: Christine Vi, Anga Ciszek, John Hanna, Eli Herlocker/Select Model Management | Hair: Igor | Makeup: Ashley Zimel/Distinct Artists | Styling assistants: Olivia Lavery, Dianeli Trinidad