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Outdoor shopping: If you want boutique-style shopping on a pretty street, go to Walnut Street in the Shadyside neighborhood of Pittsburgh. Many of the stores are upscale chains that you’ll find in malls (e.g., Banana Republic, J. Crew, Sephora, Ann Taylor), but it’s a nice setting for shopping, especially when the weather is good. There are also a number of good restaurants where you can take a break.
Department stores: Sadly, the local department store, Kaufmann’s, is no more, but you will find a Saks Fifth Avenue downtown. Otherwise, the Kaufmann’s are being converted into Macy’s.
Retail mecca: If you’re looking for big-box stores or, basically, any chain restaurant known to exist anywhere on the planet (seriously—there is a Fatburger there… aren’t those an LA thing?), go to Robinson. The big draw is the Ikea, but there’s also a large mall and stores like Target, Barnes and Noble, and Best Buy. Similar, but smaller in scale, is the shopping area at the Waterfront.
Another great new area to look at is Lawrenceville, located between the Strip District and Bloomfield. This is an up and coming arts and design area with plenty of cool boutiques and galleries on the main corridor (Butler Street.) This is definitely not a mall-type place, but an array of small, privately owned stores with an eclectic mix of craft, designer wear and furniture items. Check out DIVERTIDO (jewelry, art, gift items), SUGAR BOUTIQUE (locally made designer wear) and PAVEMENT (shoes, jewelry, leather wear) all close together on the Butler Street / 37th Street block. Also look at the Borelli-Edwards gallery and a great small bakery (cupcakes to die for) in the 35th block.