I love the vintage 1914 boots ($200). Yes, they are more expensive, but if you are going to do it, why not get the original? As of 2003 Dr. Martens moved their production to China and Thailand, but in 2007 they started making this vintage line again in the UK. These boots are made to the original spec in the Dr. Marten's factory in Wollaston, England.
Aside from the vintage style, I also like the Triumph 1914 mid-calf boot ($150). This style can be worn laced up tight or folded down to reveal the plaid lining. They remind me of Judd Nelson's character in the Breakfast Club.
I also like the lightweight tall metallic Cato boot ($150) which has a zipper on the inside for easy on and off. I'm a sucker for anything silver and I love the burnished effect that these boots have. They are also available in a less-flashy black finish.