He probably should have taken his sweater off

Should I have worn a bra to work?🤔

I should have worn a rain coat 💦🥵

Should I wear this to pick up my kid from play date?

[f] I should have worn the jacket with nothing underneath

I probably should have wore a bra but I want you to see em

[video] I've had a few people comment and say he should have

I should have worn glasses lol

I should have worn underwear

Should I have worn a bra today?

Should I have worn a bra today?

Should I have worn a bra today?