A good pair of shoes is meant to last for a long time if you take care of them. That’s how I justify spending more on a pair versus a cheap pair that lasts a season. Not to mention, cheap shoes add to wastelands and often aren’t as good for your feet.
Most expensive shoes come with a fresh leather sole. If yours does, do yourself a favor and take them straight to the cobbler to apply a rubber sole before you hit the pavement. This elongates the life of your shoes, especially if you walk a lot or if you need some traction. If your shoes come with a rubber sole, still monitor them carefully. You may need a replacement sole/heel. All this maintenance may cost the price of a cheap pair of shoes. It always shocks me how many people don’t know what a Vibram rubber sole is, so here are a few examples.
1) An old pair of J.Crew boots (circa 2004!). Don’t mind the dust…
3) Prada pointy bow flats. Previously mentioned here.
4) Marc by Marc Jacob Bow Wedges. I got these barely worn off of eBay.
5) Chie Mihara Lara Mary Jane Pumps. I accidentally dropped the shoe box down the stairs. The back heel got dented and some of the color got rubbed off. The cobbler fixed the dent for free in 30 seconds!