I love shoes, and I rarely wear the same pair two days in a row, so my shoes last for a long time, plus I take really good care of them. I firmly believe in buying quality shoes and paying to have them resoled, to have the leather refurbished, and so on. One of my favorite pairs of fall boots are some cognac riding boots I got at Banana Republic over ten years ago for about $150. I paid $30 for new half-soles about five years ago, and they still look great--classic style with great comfort that I've walked in all over the place. Paying a bit more for quality with an eye on trends that will last means that you'll end up paying quite less per wear for each shoe purchase.
Other favorites include:
Born 3-inch tobacco stacked heel mid-calf boots--$150 on sale. They've lasted, and they look and feel fabulous.
Jimmy Choo smoke-colored patent 3 and a 1/2" stilettos--$300 on sale. Same as above--much more comfortable than Louboutins.
Sofft for Garnet Hill black riding boots--$150 on sale. Super comfortable for all-day city walking--they'll last forever.
Calypso Mary Janes by Sofft--$90 on sale at Nordstrom. These shoes are the best. I got them in black and cognac when they first came out five years ago, and the company actually kept making them for several years. They have about a two-inch heel, and the heel is engineered kind of like a flamenco dancer's heel; instead of it being placed right under your heel, it is slightly curved inward toward the middle of your foot so that your balance and posture are improved as well as comfort.
Cole Haan ankle boots with 3" heels--$120 on sale at Nordstrom. These are so great and comfortable, and the leather is wonderful.
Italian sling-backs I got for half-price at Anthropologie--$150. Very comfortable 3" stacked wooden heels with a very pretty metallic and pastel-colored basket weave over the footbed. They match with so many outfits.
Gentle Souls patent leather gunmetal grey and matte leather raspberry slingbacks with closed toes and 3" stacked wooden heels--both pairs on sale at Nordstrom for @ $90. These shoes are awesome. They work in the summer with skirts and dresses and in the winter with thin socks or tights with all kinds of outfits. Businesslike, yet sexy in a smart and savvy secretary way.
Frye camel platform 4" wedges with braiding and studding details--$150 on sale at Nordstrom. These shoes are very well-made and very, very cute: Boho, girly, and rocker all at once. They've lasted a long time, and I expect them to last much longer.
Born flat summer sandals in both pewter and black leather (those were the colors I got, although more were available). These are leather thongs with a big floral detail where the straps of the thong meet, and they have the expected Born cushioning and arch support.--$75 on sale at Nordstrom. While I would never do it, it would be possible to get through a whole hot summer wearing only these two pairs of shoes.
I detest tennis shoes for any purposes other than running and working out, but I will say that I have three pairs of Cole Haan "fashion" tennies that use Air Jordan technology. These are worth shelling out around $100 for on sale as they can be very cute if you style them with the right outfit, you will be able to walk around all day in them, and they will last a very long time. In short, I believe shoes are a good investment. I wear Chakos around the house and when I go to the shore or go hiking or exercising, and those aren't cheap either, but I think they are really good for your feet and posture, and they will last forever.
OMG--did I just write this much about shoes? I could have gone on and on . . . Ask me about my purple Steve Madden scrunchy-top and pointy-toed cowboy boots.