I've already got a few favorite boutiques and consignment shops. And the sale and clearance racks at mass market stores in Chicago (ex: Anthropologie, Urban Outfitters, Ann Taylor) tend to have a better selection than the ones in New York just because they're not as picked over. I always have a hard time finding my size in New York, but in Chicago I haven't had a problem.
A couple weeks ago, thanks to a friend I had a ticket to Gilt City Chicago's warehouse sale. It was a great shopping event - cocktails, DJ, and deeply discounted merch! Apparel and shoes were all organized by size, and there was a lot of staff on the floor restocking with goods from the fitting room. I don't know how often Gilt does these sales, but I will definitely go to the next one.
Here's how I've worn my Gilt finds.
Donna clutch - courtesy of Katherine Kwei
Flower hair clips - Forever 21
Black pumps - Sergio Rossi
Black silk dress - Alice Ritter
Skinny belt - Urban Outfitters
Green satin clutch - vintage
Blue print heels - Christian Siriano for Payless
Light gray long sleeve - Uniqlo
Floral jeans - Urban Outfitters
Black bag - Hayden-Harnett
Gray boots - 80%20
My new favorite heels - Marni