My eye is massively perplexed and needs some help. I decided to give the Frye Rory boots a try during the massive 6pm sale last week; the sale was awesome, but all the same, I have never spent this much money on a boot.
I don't want to keep these unless they are absolutely killer. If I could do better, back they go. However, I am so not used to the slouchy look on myself and am feeling rather confused. And... is this a look that's likely to stay in style for a few years?

Some preliminary notes:
Comfort: The surface leather and the boot shaft IS buttery soft. The foot bed is harder than expected, but has a very gentle, comfortable arch shape. The heel feels even lower and more stable than I expected given the heel height.
Aesthetics: The "sand" color has more warmth and ruddy brown tones than expected - a plus for me, since I was sad that the cognac color wasn't available on sale. The workmanship is beautiful, and I think that the distressed-but-refined color will look good as it ages.
Ease of use: These boots were a BEAR to get on the first time. Oh my. It wasn't the calf circumference that got me since I had the boot fabric scrunched, but that the stiff part between the front and back of the boot didn't allow much give. I really had to work to get my foot in there, but it was easier the second time. I expect that the soft leather will stretch slightly as I put them on more and more, & will test this out.
Fit: The shoe runs slightly large, which I expected (I ordered down.) As I knew, my calves are too large to pull the boot all the way up, so that is not an option. I bought the boots expecting to try them very slouched & scrunched, a la Angie. Except that my calf size is way bigger, so I want to make sure it's not an unflattering look for my gams.

So what do you think?
(The outfit in these photos is probably not what I would wear with these boots - it's just what I had on. However, I'm definitely open to ideas for how to style them if I do keep them.)