July 2012: I bought a pair of Bruno Magli shoes 12 years ago in Venice, Italy. They’re the highest-quality kicks I’ve ever owned, and easily the most uncomfortable. They feel like they’re made of wood. It would be agony to wear them more than two or three hours at a stretch. But I’d rather suffer with a pair of beautiful shoes than walk around in super-comfortable shoes that look atrocious.

10.7.20: I’ve decided to get rid of some shoes that have been sitting in my closet for years but have never been worn. I’ve chosen four pairs; I’ll be dropping them off at Goodwill later today. But I couldn’t discard my 20 year-old Bruno Maglis. I just couldn’t. They hurt too much to wear more than a couple of hours, as mentioned years ago, but I cherish the fact that they’ve barely aged over the course of two Bush terms, two Barack Obamas and one Donald Trump.

I remember the moment I bought them like yesterday. Some overpriced boutique in the well-lighted San Marco district, where you’re always guaranteed to over-pay. But I was in a sucker mood. Time and again they’ve made my feet feel aching and punished, but I’ve never felt badly about owning them. Comfort is nice, but looking good is more important.