Definitely yes! My husband made an outfit and today we dropped scrubbed brush, so it's possible when you have outfit. Interestingly, I also dropped the same item during the same boss. This means that not only can we get multiple items for an outfit, there is also a chance that more than one from team will get an item during a fight.
Unfortunately, I don't have a screenshot from my husband's boss because there is a bug in the screenshot of this boss - he doesn't show us the drop, and as a result he forgot to do the manual removal. I don't have an outfit, so mine won't be any proof, but I have such a screenshot and I hope you will take my word for it.
I also found these screens on TibiaBosses.
As you can see it's possible to get both of them during a fight several times as well as obtaining the same item several times, e.g. brush twice. I think there is a chance that both items will fall down to you at the same time!