939 N. Rush St., 312-266-6000, brunellocucinelli.com
You’d be hard-pressed to find sexier sweats than the suede jogging gear at this year-old shop. With its drawstring wool pants, pleated skirts, and reversible, down-filled men’s sport coats, Cucinelli’s apparel presents endless possibilities. Seeking inspiration? The racks have full ensembles.
58 E. Oak St., 312-337-8200, christianlouboutin.com
Fashion followers can spot the red-soled Louboutin pump from a mile away. Divided into two stories—lower for ladies and upper for men—this new boutique, with its sharp angles, scarlet carpeting, and mirrored shelves displaying shiny, studded platform heels and (for the gents) tri-color Bruno Orlato flats ($995), is as dramatic as the French designer’s footwear.
25 E. Oak St., 312-337-3120, armani.com
Chicago’s first-ever Emporio Armani arrived in October 2012. The 6,000-square-foot boutique, which houses upscale-casual women’s apparel on the first floor and men’s duds (such as an ultralight leather parka, $2,625) on the second, was designed by Giorgio himself.
116 E. Oak St., 312-765-7075, lanvin.com
The three-story Lanvin, which opened in December 2012, is full of mesmerizing retail moments: the color wheel of ballet flats ($495-$1,190), the mannequin busts adorned with statement-making necklaces, and the display of iconic men’s low- ($485-$795) and high-top ($590-$1,495) sneakers, to name a few. The full collections of men’s and women’s ready-to-wear and accessories are all here.
932 N. Rush St., 312-337-3815, madewell.com
After opening outposts in Skokie and Oak Brook, J. Crew’s younger sibling moved into the city this spring. Fill your closet with as many chambray shirts, polka-dot dresses, and striped sweaters as it can handle. Finally, the city catches up with the ’burbs. (Kidding.)
11 E. Walton St., ysl.com
Back in 2010, the Gold Coast’s Yves Saint Laurent shuttered its former home, where Escada now resides. But the French brand, whose haute couture collections first garnered attention decades ago with groundbreaking trouser suits for women, was only on hiatus. Under its new name, Saint Laurent opened in spring 2013.
100 E. Walton St., 312-640-0878, sofialivelovely.com
Since 2010, Sofia (now in its third iteration and location) has evolved from an appointment-only vintage shop to a sleek women’s wear boutique. The loyal shopgirls (who double as look-book models) remain, but the store, which opened last summer, has matured into a lifestyle boutique with diamond jewelry, velvet party dresses, and studded platform booties.
945 N. Rush St., 312-340-6909, suitsupply.com
This Dutch chain’s second U.S. outpost is hidden away four stories above street level. Inside the shop, perky polka-dotted walls give way to affordable off-the-rack and made-to-measure shirts and suits (crafted from Italian fabric), plus shoes and accessories. Have coffee on the roof deck while in-house tailors stitch away.