UncommonGoods: While the products are consistently fresh and original, their website is lacking in design and usability. They're a trusted, long-time quirky goods reseller. Be sure to sign up for their print catalog -- it's nice to browse through printed materials every now and then.
Elsewares: Taking a page out of Urban Outfitter's playbook, Elsewares is another success story in peddling original, quirky stuff on the web. Popular among urban-dwelling twenty-somethings, like the above UncommonGoods, this is the place for independent artist designed jewelry, clothes and products for your apartment (err, dorm?).
Branch: Recycled and earth-friendly products are perfect for an eco-minded gift recipient. One fact I especially warmed up to is that their founder Paul Donald is a former creative from Wired magazine.
GelaSkins and Mophie: Looking for great iPod accessories? These guys have got the hottest way to wrap, protect and accessorize the most precious of mp3 collections.
NY Transit Museum Store: For those passionate about trains, or more specifically NY's mass transit, this is the place. While the subway map emblazoned apparel and bags are a bit tacky, the old subway grab holds and original subway art make for tasteful, original gift ideas.