As jerseygirl pointed out, most of Fairfield County, CT (albeit Bridgeport and Stratford) shops on the traditional historic main streets where Gaps mix in with local anitique and high-end clothing stores. Even on Ridgefield's small Main Street, pop. 7K, a Gap is just across the street from an old pizza place and next to a local art gallery. In Fairfield center, Victoria's Secret and Border's are right down the block from the Community Theatre and across from a local travel store.
This situation is largely the opposite of that of most of suburbia, mostly because of economics. One, no one here would think of setting foot in a Walmart. There is no market for most of the chains like Old Navy or Johnny Rockets. Two, the land is probably cheeper downtown. Sure, Westport or Greewich are not cheap places to buy land anywhere. But with property values in the millions, its easier to opt for an established storefront then deal with prissy neighbors who even tried to kick Martha Stewart out because her helicopter made too much noise.