strange question

I normally wear sneakers. My CFI made me wear a shirt & tie for my checkride. Obviously couldn't wear sneakers with that so I was actually concerned about taking the checkride in my dress shoes. Turns out, it wasn't a factor.
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It's a requirement at my school that pilots wear boots in order to increase the chances of surviving a crash in the winter. The only plane they let sneakers in is the aerobatic one. Also, a hat and pair of gloves are required along with a winter jacket.
 
I generally wear whatever I happen to be wearing, but when I fly the cub I wear my airwalks... the space in between the seats is just so narrow!
 
These:

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Used to wear brown casual shoes with khakis and a polo when I instructed. I wasn't big on sandals or anything, although I'm huge on them when off work!
 
Whatever shoes you wear, just make darn sure they have composite shanks!

Unless you like walking stocking-foot through metal detectors..........
 
Best pilot shoes on earth.

I can't tell if they're black or not, but I wear a black set of these:

Doc Martens:

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