I should've worn a warmer jacket.

[Marika33]

I was walking on the street with a friend of mine, and I said this "It's quite cold today", to which my friend replied "Yes, it is. I should've worn a warmer jacket".

My question is, does "I should've worn a warmer jacket" really work while the person saying this is wearing a colder jacket?
Should it be either of these "I should be wearing a warmer jacket" or "I should've put on a warmer jacket"?

 

[Piscean]

My question is, does "I should've worn a warmer jacket" really work while the person saying this is wearing a colder jacket?

The verb works, but we say 'lighter' or 'thinner' rather than 'colder' jacket.

Should it be either of these "I should be wearing a warmer jacket" or "I should've put on a warmer jacket"?

It could be, not should be.

 

[jutfrank]

In this context, worn is equivalent to 'put on'.

 

[Marika33]

In this context, worn is equivalent to 'put on'.

I didn't know that. This is the kind of explanation I was looking for. Thanks!

 

[Tarheel]

@Marika33 You might want to find the Thanks button.

 

[Piscean]

Marika clicked on it for post #3 over three hours ago.