Yeah, you got it right...
In my former career, I worked on a lot of catalogs and magazines. Territory Ahead is geared as an "edgy" LL Bean. They sometimes deliberately pick complimentary colors so you can match w/ your LLB stuff easier. J. Jill is also designed to catch the LL Beaners like TA does but they took it up a notch or two. Coldwater Creek goes along those lines too. I also worked on Eddie Bauer (don't pay their bills on time), Anthropologie (good one to check out - something for everyone), Vicky's Secret (rather snobby), Carabella's (good swim suits, better made than VS, would recommend - cheap made clothes though. The "shots" are all taken at the publisher's house in FL - he's a bit of a letch. His editing of the pics just terrified me at times. blech) Long Elegant Legs is good, for those of you who have 'em.
I say wear what you like and don't worry about what anyone else thinks. I don't look at clothes as age specific necessarily. (except some of those stretchy, flowery tops my mom wears - yech) I'm a t-shirt/cami and shorts/jeans kinda girl around home. I live in sweaters over the winter. Dress up when I need to but otherwise, very casual.