I am getting to the real pointy end of my boot search. The contenders are Frye Jane 14L in Taupe or Redwood or J Crew Vintage Roadster in Sepia and I need your help in trying to make a decision. Both of these boots fit my bill size wise (minimum 15" shaft width & max 15" shaft height) and the price seems right for both of them. I already have 1 pair of boots in my wardrobe which are a darker brown and slouchy so I'm looking for something a bit different to fill the gap. I need to be 100% sure of waht I'm getting because shipping to Australia is kind of expensive! These are the things I need to consider before jumping in with the purchase:

Frye Jane
The Taupe is on special through Amazon for $200 and in my regular size 8. The Redwood is $185.99 through ebay and is a size 8.5 (half a size larger than my normal) which may be an advantage for me being a touch bigger in the calf but dont know if it will then be too big on the footbed? The redwood color is probably also good for bookending with my red hair. I know the quality of Frye's get mentioned alot so I am gathering these are going to be boots that I will be keeping for a while? If either size happens to be a bit snug in the calf do you think a bit of professional stretching would be successful? My only other concern is regarding their slightly cowboy boot style, do you think they would be hard to style?

J Crew Vintage Roadster
Flat boot which is what I had in mind, but no zip closure. These are through Ebay for $189.99 and again they are half a size larger than my normal size. Dont know what the quality of these boots are like and also if these are good value or not?

Sorry about the essay, so if you've managed to stay awake to this part I'd love to hear your opinions!