What to Wear: City Shoes

After two years in San Francisco and three miles of walking each day, I’ve finally resigned myself to wearing comfortable shoes. It’s just impossible to get around this city in three inch heels each day. Our reader in the Bay Area has the same issue:

A couple of years ago I bought a pair of black mary janes from Naturalizer and since then it has became my go-to pair of shoes. They work all year round in our bay area weather, are very comfortable for walking on city streets, and they also look decent for casual dinners, so it is one pair that has traveled with me quite a bit.

Admittedly, they are not too high on the style meter. They have earned a lot of mileage because of their versatility, but it is time to retire, replace, and upgrade them.

Would love to get your suggestions. I don’t need an entire outfit, but just one or two shoe options that:

* would work with jeans and casual black trousers
* have a medium heel (I am petite, so added height is good)
* would be comfortable for walking around for several hours, like in museums, while shopping, or long air travel
* can work from spring to fall, in fair weather, sort of

There are three styles of comfortable shoes I rotate between every day: a low wedge, a comfortable low pump and a flat. Since flats are out for our reader, let’s find her some comfortable heels:

Work Wedge – This comfort wedge from Naturalizer is far from looking “orthopedic.” Black alligator leather with a cross-over peep toe. These shoes would be adorable peeking out under jeans or pants. On sale for $49.

Casual Wedge – These look so comfy! They’d be a great way to add a flash of color to a pair of jeans or paired with a skirt or summer dress. On sale for $44.

Mini Pump – Not the most creative or attractive shoe available, but certainly the most versatile. I have a pair of these that I wear with skirts, pants and dresses. They go with almost anything.

Sandal – Sort of a strange shoe…but one that I think would be really comfortable and cute in person. Adorable with jeans, shorts and skirts. Plus, really high user ratings. This cork wedge is from Clarks for $83.

I really need to buy some new shoes!