Everyone’s advice about handbags was so helpful that I’ve come back to ask about my worst fit problem, footwear. There’s a plethora of common sense about shoes here, which I appreciate a lot.

It may seem early to think about boots. . .Not so, if 1) you have a terrible time with boots and 2) last season’s stuff is on deep discount.

I have a tricky foot problem that makes finding comfortable and stylish shoes a real challenge. I have arthritis in the big toe joint of my right foot. The joint is swollen (bigger than the left foot), stiff (I have trouble bending it), and painful. If I wear the wrong boot or shoe, I know right away. I’m in so much pain I start to limp.

Comfort brands don’t always help—think about it, most comfort shoes are for problems with the bottom of the foot! I’m okay in that department, except for a low arch. It’s the top of the foot that causes all the trouble.

I’ve found that a padded insole helps, as does a wedge heel. I can also tolerate a kitten heel, about 1.5”, just fine, and I can walk in any heel that’s up to 2” high. The crucial thing is the toe box—kind to the joint, no seams on the sore spot. The shape of the toe box doesn’t matter—pointy and round are equally good--as long as it fits comfortably over the toe joint.

I’m looking for both an ankle boot, preferably a lower heel, about 1.5”, and a dress boot, shaft of 15”, heel up to 2”. I live in a cold, snowy climate, so I need something I can wear in freezing temperatures and walk in when there’s snow and ice on the ground. In an ideal world, the dress boot would have a narrow calf circumference, but I won’t ask for miracles. I may be able to alter a shaft that’s too big around. Either brown or black leather would be fine, as long as I can waterproof it.

It would be nice to keep the cost per pair under $200, but this may be a place to spend the money, since it’s a question of being able to walk without pain. Suggestions for shapes or brands? I’d be eternally grateful for good advice.