I remember my first pair of good shoes. They were Ralph Lauren penny loafers, which I bought as an undergrad for $125 (on sale, down from $300). That was a lot of money for me back then, and I remember taking them out of the box, slipping them on, and carefully trying them out on carpet.

The first crease you put into good shoes is always the most painful. It feels like you’re permanently damaging something new and beautiful. Not to mention that feeling you get when you first step outside and hear those leather soles grinding on hard concrete. It’s enough to make you wince.

Having owned a couple more pairs of shoes since those loafers, however, I’ve learned that the value of good footwear is all in how they age – much like the value of good, raw denim. In fact, that’s the only reason to spend so much money on shoes. Despite what some people say, Goodyear-welted or Blake-stitched shoes will not save you money in the long run. A decent resoling job alone can be more than a pair of cheaply made kicks.

No, the reason to buy good shoes is because they look better with age. Assuming you take care of them, of course. That means inserting cedar shoe trees when you’re not wearing them, using leather conditioner and shoe polish on a regular basis, and rotating between shoes so you’re not wearing any pair for two days in a row.

If you do that, your shoes will build a patina, like you see above. Covered up scuffs will become light colored accents, highlighting the varying shades of color that have been built up from years of applying shoe polish. Regular treatments of leather conditioner – along with an occasional treatment of wax polish – will also make the leather glow. At that point, you’ll always want to resole your shoes, rather than buy new ones.

(photo via chriscrat)