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555 N. Michigan Ave.; 312-494-8580 (and other locations)
SAVE In the spring, the Gap started carrying Chuck Taylor Converse sneakers and, although the familiar low-slung court shoe can be found elsewhere, we have yet to find a better mix of colors and styles. For men, they come in fashion-compatible black, white, and loden green. For women, we spotted a rad silver pair (pictured). There’s also a great laceless slip-on style for $45 that may be this summer’s perfect weekend shoe. Best of all, along with the rest of the store’s merchandise, the shoes are regularly marked down.
923 N. Rush St.; 312-932-0651
SPLURGE Carrying only legacy lines from the 1970s through roughly the early 1990s, this concept boutique from Adidas, the German sportswear maker, is a retail museum of past sneaker trends. The popular Adi Racer Low ($80), a foot-hugging driving shoe, was the product of a collaboration with Goodyear, the tire com-pany. The Decade Hi ($130) is a stitch-for-stitch reproduction of an all-leather basketball shoe from 1984. The shell-toe Superstar line, the Run DMC shoe, sells for $65 a pair—but go for the cooler black ones with white stripes ($60).