Just as background, these are my 4th pair of Frye Boots. They join the Melissa Logo (stiff, no-nonsense equestrian), the Harness 12R, and the Veronica Combat.
I purchased the Jane Strappy in dark brown.  I have found that brown boots are every bit as versatile as black and you cannot beat the richness of the color.

I find Frye sizing to be extremely consistent.  An 8.5 fits me perfectly for all the boots. I disagree with the many reviewers who advise to size down.  These boots are a big investment and I wouldn't count on them stretching all that much. I have had the Harness for over a year with heavy wear and they do not seem to have stretched. I wear a 7.5 or 8 in other shoes, but I go up for boots to allow for socks. Feet do swell after a few hours of wear, so my advice to to keep them roomy.

The Jane Strappy is an unlined, slouchy style boot, so keep that in mind when ordering. I love the look of them with skinny jeans.  They fit my calves fairly loosely so there is quite a bit of room.

The only thing that made me hesitate was the price tag.  Even so, I LOVE these boots!  They have a very unique and sexy vibe.