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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.

Adidas Originals
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).