Dear Ask Anything,

So the other day I was browsing online for a new pair of comfortable gray shoes and I ended up purchasing a pair of TOMS. It wasn’t until after I bought them that I realized these shoes are apparently important artifacts in the hipster subculture! Now I certainly wouldn’t use the word “hip” to describe myself. Was I wrong in my purchase? Will people think I’m too pretentious? Can a non-hip person wear hip shoes?

Sincerely,
Fashionably afraid

First of all, you did a good thing. TOMS is a wonderful, charitable organization that donates a pair of shoes to a child in need for every pair sold. You can be comfortable with yourself, because despite maybe paying a little more than the shoes are worth, you’ve done a good deed.

Your problem isn’t with buying the shoes; your problem is with wearing them.
You’re worried that if you wear these shoes in public, your peers will automatically think you listen to Hot Chip and own an iPhone, which would lead them to assume that you really like coffee and J.D. Salinger novels, which would then make them write you off as a Pitchfork readin’, fixed-gear ridin’, no good, dirty, rotten hipster.

There are exactly three pros:
1.) You don’t have to wear socks. Granted you don’t ever have to wear socks, but with TOMS, not wearing socks is encouraged.

2.) TOMS are actually pretty comfortable.
3.) None of your grievances matter. Not one bit. Here’s what you do: every time you look at those little shoes and have a mental conflict about whether to wear them out or not, you should think of the child that now has shoes because of you and you should realize that that child wouldn’t care about people thinking you’re pretentious or asking your opinion on the new Arc

ade Fire album … so you shouldn’t either. That child is just happy because you gave them shoes, so give yourself a pat on the back and wear them with pride.