I suggest stalking your local Marshalls and/or TJ Maxx, if you have one. At the beginning of the last two falls they had some beautiful boots that were obviously a buy out that they did from Bergdorfs, Henri Bendel and other higher end department stores. They had boots with the original Bergdorf tag on the box that said $750 for some that were priced at $29.99 to $39.99. They were definately one offs so you are not assured your size, but it is worth it if you find the right pair. This is usually early or pre-fall, so start looking around mid August. I lucked out last year and bought several pairs of gorgeous boots. I can't wait to wear them again this year.
The stores have just begun getting their boots in for Fall, so I'd start looking around but not buy a pair until at least the end of August. You'll get the best variety by then and most likely there won't be any sales before then anyway.
I love Frye boots for sturdy, well made leather boots. There's a reason you can still wear (and buy on ebay) Frye boots that are a decade or two (or even three!) old. They're expensive, but you can wear them forever. Sometimes DSW has last years styles for a little less, but it's hit or miss of course. On-line codes help too.
OK, I have found some boots....tell me what you all think....
These are a little....too girly for boots. But very cute if they werent so expensive and if I wouldnt feel bad about not wearing them all the time.... $248
Not really a fan of the ones with the row of bows. They're too cutesy for my taste and I think I'd tire of them easily. Also not digging the black soles on the Madewell ones.
I really like these, but they look like otk boots to me. If you are looking for classic brown boots, I'm not sure if these are something you'll be wearing 5 years from now (or even 2.) If you already have classic boots or if that's not what you want in the first place anyway, I think these look really sharp.