Oh yes I remember meeting you at the YLF dinner. That was so much fun.
If you want a heel that is very comfortable and walkable, anything in the Jane group has the same shoe part, different shaft style. The Rory Scrunch boots also have the same shoe part as the Jane boots, different shaft. By that I mean the same sole and heel shape and size, so the boot will feel the same on your foot. When you go to the styles that have a taller heel, like the Julia and Fiona, they are getting into high heel territory and not comfortable to me, but oh so pretty.
I really love the Melissa button boot. On the website they describe it as a vintage looking riding boot. I think I am going to try those next. I love the look and the colors.
I like Cathy's new spring boots with the perforated shaft. I think they are Carson's in buttermilk color. Please correct me if needed Cathy. All Carsons have the same shoe part to them so the Carson shorties will have the same boot fit as the Carson pull ons, and the fit is great. They are low heel, comfortable and not to cow girl, just a little.
I'd watch to make sure the boot you order has a thick enough sole. Some Frye Riding boots, like the Shirley, have a thin sole and very low heel and I didn't like the feel of those. The Dorado Riding boot is great with very thick leather and a good boot shape, and thicker sole. I had the Paige Tall Riding boot to try out for a while but they have a very round toe and very flat heel, so I decided they were not really my type. To see how round a toe is you can flip over to Zappos where they show you the boot from the bottom and all around the boot.
http://www.thefryecompany.com/women-boots.aspx
You can open this link and click the tab to show ALL the styles on one page. Just look at them and compare and take your time. Eventually you will zero in on a few that you know are what you are looking for. Call the phone number and ask many questions. I have done this a few times and they love to help as much as they can. Many of the gals there have a closet full of Fryes. I learned from them to look at the styles, as style groups, and I wish they would organize the boots in order like that, but you can learn to see the similarities in name and fit style.
I'm also very interested in the Samantha Woven right now. There is a Shirley Studded Hurache boot too, which is a bit more casual and scrunchy, but the gal I talked with told me they are beautiful. Again they are "Shirley's" and have a thin sole, to me. I think I like the look of the Samantha.
Some people love all of the campus and engineer styles. I guess I am too old and missed those styles in my youth, so I focus on what speaks to me, and it takes time, but it's fun. Enjoy! If you do not wear your boots outside untill you are sure you want to keep them, the return and exchange policy is good.
Sorry this is getting to be a book, but I forgot to mention color, so many great colors, and the "fawn" is gorgeous.