School shoes (boys)
At my school we have to wear proper black leather shoes with our uniform. The rules are quite strict (no trainers/boots/fashion styles) and most lads stick to them. Problem is, that the shoes my parents get me for school (I have a bit of choice but not much) always tend to be really stiff and uncomfortable. Its the same every year, when I get bought a new uniform.
Although most boys here tend to end up with the same sorts of shoes - clunky, heavy and they kill your feet having to wear them all day! Its no wonder most lads slip them off in class and stay in socks instead. I can't wait to get home from school and kick them off at the door and relax my feet.
My feet are size 11 (UK). Now call me crazy, but I tried on size 16 shoes, and they were so comfortable, I actually wanted to buy them, and it's practical because I'm not going to have to buy black shoes again for the rest of my life probably.
I ended up buying the normal size 11s, because my friends thought the idea was too stupid.
Yeah, same when I was at school. My parents would buy me the stiffest, heaviest most formal "school shoes" they could get on a budget. And they would cripple my feet having to walk to school each day. But at least I wasn't alone - quite a few lads used to end up with the same shoes as me.
I used to get a size-larger just so as they wouldn't feet so uncomfortable, and tied the laces very loosely so they'd be easier to slip off under the desk without anyone seeing. Some lads used to try and wear trainers instead, but if you got caught in trainers, they were confiscated for the day.
It was such a relief to kick your shoes off for PE or drama or just to get home and finally be free of the wretched things!
I would wear my trainers so they would get confiscated for the day.

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