East 57th St, Upper East Side

There is a lot of the kind of UES shopping that you see in movies about New York on East 57th. If you've got money and want to find a place to spend it, this is a great place to start. It starts off with a bang with the Tiffany's store. It's the one where Holly Golightly goes in Breakfast at Tiffanys. I'm not a huge fan of Tiffany, but this store is really beautiful. This block between 5th and Madison holds YSL, Chanel, Dior, Furla and Burberry just to name a few. It's a pretty high-end block and you'll be hard pressed to find any hipsters lurking about here. The block between Madison and Park is equally as high end just with a different sort of commerce. The IM Pei designed Four Seasons Hotel is on this block, and I hate to say it, but it really is a beautiful building. It looks a lot older than it is.
More high-end buildings continue as you head further east. They're all huge and crazy expensive. The Ritz Tower is probably best known as the building where Hearst kept his mistress, Marion Davies, the whole time they were shacking up.
Once you get east of 2nd Ave, though, you're getting into the really high-end properties. The area known as Sutton Place is one of the most expensive neighborhoods if not the most expensive neighborhood in Manhattan. JD Salinger lived at 300 East 57th just after Catcher in the Rye. Lillian Gish, Marilyn Monroe and Arthur Miller, and William Saroyan all lived on the block between 1st and Sutton. There's a really neighborhoody vibe in this area -- even more so than the West Village. It's glorious here, if you can afford it.