Pros
Great clothes, great people, reasonably laid back work environment. The girls working at Madewell are usually fun and chatty. You'll do well if you are honest with customers, know the product well, and have good taste. The discounts are pretty good but there are a lot of things (leather items, some new items) which you get 0% off of.
Cons
Very hard to move up. Takes tons and tons of observation to be promoted from Associate to Stylist. If they notice you are talented at Sales, they will use you in the stylist role without actually giving you the new title, pay raise, etc. Very frustrating. Usually, stylists tend to be very secure in their position, so they slack and eager/talented younger associates will pick it up while the stylists take all the credit. Can definitely feel like there is a divide between associates and stylists.