I swore off buying shoes online (sort of... at least partially swore off...) And I rarely try on shoes at stores. Taking my shoes off in a public place would be like an invitation for X to run away. So I've basically had a shoe-buying moratorium. Which is fine for cold weather, because I only wear four pairs of shoes: my beloved Clarks Dara III ankle boots in brown and black, plus snow boots and a pair of casual Born mostly-flat ankle boots for the weekends. My feet are hard to fit, and ankle boots are comfortable and easy. The Clarks Dara boots are also waterproof and nice enough to wear to work. But my black boots are showing their age, after four years of heavy use and multiple heel repairs. I found a place that does full resoling for Clarks shoes, but it costs $60 plus shipping. Today I found out Clarks is having a sale, and I got a $20 off code, so I got new ones for half price! Yay!! I'll probably stick out the rest of this winter with my old boots and then switch to the new ones next fall.
For summer, I have three identical pairs of cheap pumps, in pewter, taupe, and brown, that I keep under my desk. I wear commuting shoes to work (usually my Born Mary Janes) and change into heels when I get to work. On weekends, I wear flip flops or comfortable walking sandals. I'd like to upgrade my warm weather shoe wardrobe. My feet have permanently grown post-pregnancy and many of my old shoes don't fit well anymore, and my work shoes aren't in the greatest shape. But it's a lot tougher to find warm-weather shoes that fit right. I probably need to do some actual shopping, or at least order a bunch of things and return a lot of them.
What's your shoe routine?