No one asked me, but I’m gonna tell ya anyway… Aside from the very rare instance of having to wear dress shoes, I have worn the same three pairs of shoes for almost the entirety of my life. This is them:
- Vans slip-ons. I buy these almost exclusively in the all black color way. They aren’t all that comfortable and I don’t necessarily love the way they look… BUT, they are easy to put on and they work with just about anything.
- The Red Wing 1178 Boot. If I’m doing dirty work in the shop, I wear 1178s and have since I was 15 years old. In fact, I am on my second pair and have probably gone through a resole every five or so… They are indestructible, comfortable, and unmatched by any boot ever made.
- The Jordan 1. I have worn Jordan 1s since grade school and continue to wear them to this day. But about a decade ago, I bought three pairs of Jordan 1 “Banned” bred toes at retail and have worn out two pairs. They go for over $2000 a pair now, but I don’t give a shit – I will wear my last pair until they die, knowing that I will never own another.