Breezing Down the Windy City’s Posh and Charming Oak Street
Oak Street means elegance, fashion and exceptional service. This oasis of style is in the heart of the Windy City near the Drake Hotel and next to the Magnificent Mile.
Surrounded by Chicago’s business bustle, Oak Street is a quiet, charming, tree-lined refuge from traffic. It is decorated with flower boxes and old-fashioned street lamps. Its distinctive charcoal gray sidewalks are flanked by Victorian town houses.
In the block between Michigan Avenue and Rush Street, Oak Street boasts a roster of distinguished boutiques and gift shops, each offering a variety of unusual, high-quality merchandise. Fabulous window displays provide entertainment for strollers.
Oak Street compares in quality and types of merchandise to New York’s Fifth Avenue, Milan’s Via Montenapoleone and Paris’ Rue St. Honore. But Oak Street also specializes in friendly and accommodating service, beginning with valet parking and further realized with warm welcomes from attentive but not overbearing sales personnel. On Oak Street, posh doesn’t mean snooty.
Retailers stock items with a wide range of prices. Oak Street is geared toward the well-to-do, but buyers with modest budgets can find affordable finery, too, especially during block-long clearance sales in January and July, when all Oak Street shops reduce prices up to 70% on all their merchandise.
Oak Street’s shops include designer boutiques. Rodier (No. 67), Gianni Versace (No. 101), Sonia Rykiel (No. 106), Bottega Veneta (No. 107) and Giorgio Armani (No. 113) all feature fashions bearing their sought-after labels.
Exclusive Styles
Other top designers are represented in several superb fashion emporiums, many of which have styles created exclusively for them. Most famous of these is Ultimo (No. 114), whose stock includes Krizia, Valentino, Gaultier, Yamamoto, Comme des Garcons, Alaia and others.
Ultimo is about as close as Chicago gets to haute couture , and owner Joan Weinstein--known well beyond the borders of the Windy City as a barometer of contemporary fashion--is almost as famous as her clientele, which includes David Mamet, Gene Siskel, Eric Clapton, John Malkovich, Oprah Winfrey and a slew of socialites. It is said that the majority of serious Ultimo shoppers spend between $4,000 and $10,000 a year in the boutique, but there is no minimum purchase required and browsing is free.
Bottega Contessa (No. 106) showcases owner/designer Contessa Helena Kontos’ dramatic, unusual sense of style. The countess mixes classical and exotic fashions by George Rech, Kabuki, Ferre and other pricey designers, and sumptuous leather creations by Roberto Cavalli ($400 and up), with her own intriguing ensembles and accessories. The countess’s look is feminine and seductive, with deep V-necks, bare backs, slit skirts accentuated by contrasting lace or with enticing veils and loosely draped fabrics. In addition to the unusual clothes the shop offers great service. Styles will be fitted and altered to fit the body and personality of celebrities (Oprah Winfrey, Natalie Cole, Lana Turner), socialites and other customers.
Terri D. (No. 59) belongs to former model and current style-setter Terri D’Ancona, who stocks famous labels but also sells terrific items from Chicago designers. Especially exciting are Maria Rodriguez’s hand-woven tweed mix-and-match casuals, with fabulous black-and-white blazer ($252), T-shirt ($110) and trouser or skirt ($122) ensembles. Reginald Thomas’ one-size-fits-all coats in cozy knits ($152) and reversible vinyl and knit ($252) are versatile.
Kanae makes appealing and tastefully avant-garde jersey top-and-skirt outfits (about $180). In addition, Terri D.’s is a constant happening of salespeople outfitting customers, designer trunk shows, and fashion shows in which local celebrities and socialites model for their favorite charities.
Evening Attire
Pompian (No. 57) features a wide range of styles by upscale designers including Nancy Heller, Byblos and others, as well as Peggy Martin’s full line of classy, color-coordinated and comfortable jersey knits (about $85 or more per item), plus dazzling evening attire such as Tom and Linda Platt’s clingy red satin strapless dress ($800). In its upstairs gallery Pompian has leathers, including Bergador’s green calfskin (with a crocodile pattern imprint) greatcoat ($1,300) and durable, stiff-sided, huge cowhide carry bags ($160) in black and brown.
Sugar Magnolia (No. 56) is run with style by owner Leslie Gersten. In the store are fun young casual clothes by CP Shades (about $40 per item) and other trendy labels. Skidz shorts ($30) in a rich array of colors can be matched with Sugar Magnolia’s exclusive T-shirts featuring elaborate rhinestone cowboys ($68 to $100), beaded bars of music ($48) and other imaginative goodies. There are also flowery sun dresses ($70), skirts ($58) and tops ($48).
My Sisters Circus/Isis (No. 38) stocks Tornado’s cotton knits (about $90 per item) made with beautifully patterned textiles in basic black and gray or vibrant purples and pinks to create a layered look. Laise Adzer’s gauzy styles are also featured. The shop sells terrific foam shoulder pads ($12) that don’t require pins or Velcro to stay in place.
For Your Active Life Styles (No. 47) has unusual and amusing workout togs, including tie-dyed leotard tops ($38) and tights ($40) in a rainbow of colors, plus hand-painted, sequined sneakers ($40) and designer Phyllis Blumenthal’s oversized T-shirts enhanced with patches of lacework and beading ($110).
Jean Charles (No. 30) appeals to trend-conscious shoppers with the latest in moderately priced Parisian labels. Samurai tops (around $80 and up) are stylishly cut on the bias, studded and stitched. In contrast, there are coquettish tops with puff sleeves and polka dots ($40), and matching skirts with ruffled layers ($68). The front of the shop features great French footwear, including pumps (about $100) with all heights of heels.
Unusual Shoes
Posh (No. 50) specializes in distinctive shoes by Manolo Blahnik, Roger Vivier and Mario Valentino. Owner Catherine Levy has several other designers who provide exclusive styles for the shop. It is frequented by some of Chicago’s best-dressed women. Unusual items include Pupi D’Angieri’s cream-colored boots with strips and patches of lizard, snake and other exotic leathers sewn into latticework patterns ($375).
Smith Bros. Shoe Parlor (No. 33) has an intriguing collection of classical shoes, plus a selection of walking shoes and dressy slippers ($38 and up).
Oak Street has three men’s boutiques. Stuart (No. 102) features the latest and best in high-priced suits, from Missoni Uomo and Ferre’s 000.1 collection. In Chicago specializes in top-quality casual wear and has a selection of sweaters ($85 and up) and cotton shirts ($45 and up). The Brass Boot (No. 55) is filled with exquisitely made men’s shoes, mostly Italian imports with butter-soft leather in a variety of styles and current colors, and a handsome section of jackets for all occasions.
The Water Mark (No. 109) is a gem of a stationery store, featuring teddy bear greeting cards with movable parts ($3), handmade writing paper ($7 a sheet), unusual invitations to be engraved to personal specifications (prices begin at $70 for 25 invitations), antique desk sets and accessories, liquid calculators ($35) and tooled leather agendas ($56).
There are colorful African baskets ($20), one-of-a-kind decorated file card boxes ($110) and photo albums covered with Thai tapestries ($450). For $5.50 and up the Water Mark packages gift items in tin cans (some play music when they’re opened) with special labels.
Gift items sold at La Bourse (No. 67), an elegant and fun thrift and antique shop staffed by volunteers, benefit the Chicago Medical School. Items, ranging from $10 and up, include silver picture frames, crystal serving dishes and goblets, desk and dresser sets, porcelain, lamps and furniture.
