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600 N. Michigan Ave., 312-642-9613; 1552 N. Milwaukee Ave., 773-486-3900 (plus an Evanston location)
SAVE In the overheated market for premium denims, there was a time when Levi’s seemed destined to sink into squaresville oblivion. But the San Francisco–based jeans brand has successfully stepped up its game in recent years to the point where it now is the credible denim outfitter for guys who want to look hip without seeming to try too hard. The new, slimmer-fitting, lower-rise styles in trendy washes (pictured) are still offered at good old Levi’s prices: from $45 to $70, for men—and women, too.

Krista K
3458 N. Southport Ave.; 773-248-1967
SPLURGE If you’ve ever been to the denim basement at Krista K after a big sale you might think the store’s selection is hopelessly mixed up. But it’s only because the city’s jeans fanatics have been there and ravaged the place. And, whereas E Street Denim in Highland Park seems to cater to North Shore teens, this boutique carries jeans for all—to our eye, the best and widest selection of fits, washes, sizes, and brands from the known (Chip & Pepper, Citizens of Humanity, Genetic, James) to the new (William Rast, Anlo, and Raven).