Difference between на and в in clothing?

Question

Rosetta Stone is trying to teach me there any difference between `Мужчина в туфлях` when it previously taught that на should be used for wearing clothing with words such as туфли, шляпа.Is there any difference?

Answer 1

The preposition "на" can be used when you rephrase this combination of words saying "на мужчине туфли" (= мужчина в туфлях"); "на мужчине (была) шляпа" (= "мужчина в шляпе"). To tell the truth, the combinations with the preposition "на" are used not as often as the ones with "в". There are numerous examples in the Russian Internet proving this, for example,  "Мужчина в кожаной куртке был остановлен на улице..." or "...Клод Моне рисует Камиллу Донсьё, а картину называет «Камилла, или портрет дамы в зелёном платье».

Answer 2

I am not familiar with Rosetta Stone, but `Мужчина в туфлях / шляпе/ галстуке/ костюме` is correct. I am not sure you can use на in this context.