Do you wear any shoes that have a rise in the heel, or do you only wear totally flat shoes? There is a big difference between getting used to shoes with a rise, and shoes with 'heels'. The issue with a rise is that it will work your legs and glutes differently. The issue with heels is they get stuck in gaps between stones and bricks.

you know how I feel about my merrells.

I'd say that's the tactic that has worked for me: be willing to pay a premium for high-quality shoes and choose for substance over style. Which is not to say my shoes aren't stylish, but I limited my search to brands I knew would be good for walking and chose the prettiest from among those.

It's super easy: put the heels in your bag and walk a couple of miles in real shoes. Arrive and your destination and put your heels on. Reverse process to go home.

I tried for about a year and a half to wear heels on my commute. I got sensible, cute, expensive heels from those companies that believe in "walkable" girl shoes. They were walkable in that they didn't pinch my feet and I didn't get blisters. But after about a year, my back said FUCK YOU. So I still mostly get comfy ones, but I also just bring them when I want them.

This has the added advantage that when I do wear real, fuck-me, non-sensible heels out on a date, it feels like bondage. This may be of limited use to others, depending on their taste.

i was also going to suggest wearing one pair, and switching them out. keeps the nice shoes nicer, and saves your back, legs, and feet.

I currently live at the top of a steep hill that's on top of a less steep hill, so I've also employed the method of wearing flip flops and carrying heels until I get to the T or to my destination, whichever is easier/more appropriate to make the switch. But I've been looking for a low, interview appropriate heel for awhile and found these this week. I've walked several miles in them in the past two days without any problem.

I agree with the comfort of carrying flat shoes, but honestly I can't be bothered most of the time. I'd rather just have comfy shoes, and I find that there ARE comfy heels out there.

Key is to look at stocky heels or "cuban" heels rather than stillettos. Wedges, as arachne8x says, don't get stuck but I find they allow for less flexibility in the sole and are less comfortable for navigating stairs. Height is also key. Start with a low heel and increase as tolerated. Lastly, think of the toebox. Open toed shoes tend to concentrate all the increased toe pressure into one tiny space. I always go for completely open sandals or closed toes, but not the 1 or 2 toe revealing shoes that just squeeze your foot like a toothpaste tube. And if you're worried about pumps falling off, you can always go for "mary janes" that have the cross strap. It enables the shoe to have a little bit more room rather than staying on your foot through sheer compression.

I very much enjoy these shoes for being cute low heels that are quite comfy. Another tack is to buy "character shoes". These are a specific style for dancers that are intended for heavy use and comfort, but are still very cute. I started with these when I was doing 4hrs of ballroom dancing two nights a week and as you can see by the Rocha's I've never really given up the style.

Hope this helps!

This. But I have more thoughts as well.

Be aware of the shape of your feet. Flat, medium, high-arch? Not just wide or narrow, but which part of your foot is wide or narrow. (Frex, I have narrow heels but medium-wide balls.) Are your feet in good shape? If so, you may be able to get by with less expensive shoes.

Think about what sort of heel you want. There's height, of course, but also shape. I usually go for large heels - they might be 2" by 2", aka the whole back of the shoe is elevated. Different sorts of heels are appropriate for different situations, and I don't know enough about yours even being to opine.

Some brands make very "high" quite comfortable. I find that 4" heels from Ferragamo to be more comfortable than 1.5" heels from anyone else.

Quality protects your feet, and quality costs. I don't know why it's not possible to buy good quality shoes at discount prices, but it's not. Also, I recommend against buying used shoes. They're usually *very* worn, have lost support, and while they've been broken in, they're broken into someone else's foot shape and usage.

Nordstrom has the best shoe department. Their clerks really know their stock and actually pay attention to not just what you want, but what your feet might need. They'll also take anything back. My usual is to wear new styles around the house for a week or two, then return if they're not comfortable - Nordstrom has never so much as blinked at this. But I've returned shoes worn outside as well: the dye on one pair got spotty after 1 week wearing outside; Nordstrom took those back as well, cheerfully and with an apology to me.

this contains most of my suggestions -- character shoes, maryjanes and t-straps which are currently fashionable (because I can't stand the "my shoe is about to fall off" feeling of shoes without a strap across them), and elegant-yet-chunky heels because it decreases the enormous ankle-stability strain. i don't trust myself to wear pointy high heels because i can sprain my ankle in flats all by myself.

fluevog makes very well-balanced heels, as do clarkes and miz mooz.