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I have used a sentence like "Be careful of wearing a coat." and I wondered if it was a normal sentence a native speaker would say.
Looking at the OALD, I noticed the following example:

I'm very careful about washing my hands before eating.

The dictionary adds between parentheses:

I make sure I do it.

Does that mean be careful can be used to mean "make sure"? Would my example sentence be understood to mean "Be sure to wear a coat."?

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In some contexts, "to be careful" can be used to mean "I have an ongoing habit of making sure I do [x]". This is the case in your hand-washing example; "I'm very careful about washing my hands before eating" means "I always make sure to wash my hands before I eat".

It doesn't work quite the same way in a command, though. If you're telling someone to be careful about/while doing something, you're cautioning them. For example, "Be careful when you cross the street!" is said to make sure someone uses caution and isn't hit by a car, not to tell them to be sure to cross the street.

So, in your example sentence:

"Be careful of wearing a coat."

This doesn't mean "Be sure to wear a coat", but actually the opposite; it's a caution against wearing a coat. It would be understood as:

"Take caution when you wear a coat! When you wear coats bad things can happen, and you need to watch out."

Which is probably not what you mean to imply!

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    But "Be careful to wear a coat." does mean to make sure you wear one. – Jim Mar 10 '13 at 2:06
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    @Jim: excellent point. Be careful of using the wrong preposition. Be careful to use the right one. – Peter Shor Mar 10 '13 at 2:08
  • @Jim I don't know that I'd expect that sentence from a native. 'Be careful and wear a coat', maybe. But that separates the care and the coat, so isn't in OP's scope. – mcalex Mar 10 '13 at 2:19
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    @mcalex- google.com/… – Jim Mar 10 '13 at 2:58

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