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:

1. 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.
2. 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.
3. 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.