Kirkwood Avenue
Kirkwood avenue is the street leading from the downtown square to the sample gates, the main entrance into the beautiful indiana university campus. it is iconic of indiana university, and especially bloomington. it offers a couple of clothing shops, a souvenir shop as well as an indiana university gift shop. it's usually packed with iu students, so take a stroll, find some grub, do some people watching, or some shopping.
College Mall
Located on the east side of town, college mall is a typical small town shopping mall. it's nice to spend a few hours in it at one a rainy day but don't expect too much. anchor stores are target and macy's, and also has build-a-bear workshop, victoria's secret, old navy, abercrombie & fitch, several video game stores, wet seal, yankee candle, american eagle, and more. food options include a couple pizzerias, auntie anne's, subway, and a brand new food court with several new eateries.
The Westside
Up and coming shopping/eating area with tons of shops and good eats.
Landlocked Music
Buy local and that does not exclude music. a great variety of new and used albums. if they don't have it they will order it and you'll pay less than you thought you could. from independent to major label, this is the definitive music shop for the midwest. run by people who are modern music historians. [www.landlockedmusic.com]
Bloomington is the place to go to do some unique shopping. There are plenty of stores that are familiar to everyone as well as a few you WILL NOT find anywhere.