"I have loose ankles (my ankles twist really easily, the opposite of strong ankles, I suppose -- if my shoes don't have a supportive heel, my ankles will be twisting all day) and my left arch is quite high, so I have to make sure that the boot is a neat fit for support but doesn't put pressure on the top of the arch, and that my heel has an adequate platform to stand on. I must have a full zip, otherwise I can't get my foot in. There mustn't be any seams on top of my foot because these create pressure points. I definitely have to stand and walk around in the boots for a couple of minutes to make sure there's no excessive sideways wobble and that I can confidently put most of my weight on my heel. This fact alone makes me hesitant to try mail-order boots, as I might love the look of it, but there's no way you can tell by the picture if boots have too much slope under the heel so that most of the weight is constantly sliding forward onto the ball of the foot. I think that would always be the case once the heel is over three inches, and these are the boots and shoes that give the wearer very sore feet after a short while. The ball of the foot is not designed to carry one's full weight for any length of time.
"The only difficulties I have with high heels is when driving and trying too walk fast! I fix the first problem by having more comfortable footwear along for wearing in the car, and the second just requires practice.
"For the rest of the purchase decision, it's a matter of finding decorations I like [accents such as tassles, studs, or ruching], and a toe shape that fits and suits my foot. A softly pointed tip (nicely rounded) looks good on my feet and fits my narrow foot and tapering toes (second toe longer than the rest)."
An avid boot lover, who admits to owning 7 pairs, says:
"When buying boots, I recommend you go for comfort. There are some lovely flat boots around if you want to be mega-comfortable, but if you want to feel a bit fancier and want a heel, I would say a wedge is a great idea. They're fashionable, but comfortable and they don't have the teeter factor that thinner heels have. I stomp around in mine all day long and don't get sore feet and I have very wimpy feet. Overland Shoes have some of the nicest and most comfortable boots I've ever tried on. They have an Italian brand called "Isabelle Anselmi" and though they're usually a couple of hundred dollars a pair, they last forever and are lovely.
"My favourite boots are the ones I'm wearing now. They're a rich chocolate brown with a stacked wooden wedge heel. I polish them with bees wax.
"I think the look of boots with a mid-calf length straightish skirt and a long coat looks great in winter!"
For expert advice on boot care and how to measure your feet, ankles, and calves to get the appropriate size and style, visit DuoBoots.