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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?

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Мужчина в туфлях had the meaning "man wearing shoes". The important rule is that sentence tells you about a man as the main subject of the sentence who wears some piece of clothing (which is not a main subject, but an attribute to describe the person) - a man or woman wearing something should be described normally using в. 

Мужчина в одежде
Женщина в платье \ в пальто \ в шапке

Use на is when wearer is NOT a main subject of the expression, and piece of clothes IS THE SUBJECT. Then use the clothing name followed by на and reference to whoever has that piece of clothing on. 

Пальто на жещине
Одежда на мужчине

hope this gets you the idea.

UPDATE: as noted in the thread, if we talk about a woman on high heels,

женщина В туфлях НА каблуке

is correct. So woman is В туфлях and shoes (in turn) are НА каблуке. Some sort of nested structure. Same rule works.

There is however some sort of shortened version of this that may be of interest:

женщина на каблуках

It is viewed as not "wearing" but more like "standing on". So "wearing" convention for в\на may no longer be relevant. In that sense "на" can be used for a person in relation of heels.

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  • A little bit of obscenity: "мужчина на женщине" and about pregnant woman : "ребенок в женщине" ))
    – Alex Yu
    Dec 27, 2015 at 22:37
  • @Ingaz yeah, but this is more "physical bodies" relative to each other, so quite literal. It is not related to act of wearing a clothing.
    – onkami
    Dec 29, 2015 at 10:39
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Мужчина в туфлях (в ботинках; туфли из more typical for women to wear) translates as 'a man wearing shoes' (literally, with shoes on his feet).

На мужчине (были) туфли is a possible expession to describe someone's appearance; it includes a verb and is more like 'that man has (had) shoes on his feet'.

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    It might be that in your region someone calls these google.com.ua/… ботинки but the only name for them I've ever heard is туфли . At least in vernacular language. And these are google.com.ua/… ботинки
    – Dmitry Koroliov
    Dec 19, 2015 at 5:13
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    @user907860 Formatting tips: Ботинки versus Туфли
    – Eugene
    Dec 19, 2015 at 6:14
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    Actually "ботинок" is "high shoe", and "туфля" is "low shoe". Both men and women may wear either high shoes or low shoes.
    – Matt
    Dec 19, 2015 at 7:52
  • I think there is clear difference in word usage about what men wear, depending on where it is said: in a shoe shop or somewhere else. In a shoe shop for men the Russian for high shoes is "ботинки" and for low shoes it's "полуботинки". Sometimes that product is called "туфли мужские" where the word "мужские" is an important modifier: if you google-picture "туфли" from a Russian IP, you'll only see women shoes.
    – Alex_ander
    Dec 20, 2015 at 7:52
  • Outside a shoe shop any shoe version men wear is called simply "ботинки" unless recent shopping is mentioned. Being a St.Petersburg resident, I almost never hear "(мужские) туфли" in everyday life, though It might be different in Ukrainian Russian, etc.
    – Alex_ander
    Dec 20, 2015 at 7:53
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In this case you can just apply a direct translation and be good: в = in, на = on.

So "a man in hat/shoes/gloves/etc" = "мужчина в шляпе/туфлях/перчатках/и т.д."

"Hat/shoes/gloves/etc on a man" = "шляпа/туфли/перчатки/и т.д. на мужчине"

"Штаны на ремне" = "pants on a belt", I don't sure if it is the way to actually say it in English, but the meaning is quite obvious, and the pants are holding on that belt, not in it.

One not so obvious case I've found is "ходить на высоких каблуках" or "носить обувь на высоких каблуках". As I see it is rather "in high heels" in English, but this just because "high heels" is used as "shoes with high heels" equivalent, and one wearing shoes is in the shoes, not on it. But if your shoes have any heels, you are definitely standing on that heels, not in them.

So, the words and the context translates quite straightforward. You can say both "в/на высоких каблуках" regarding to wearing such shoes, but if there is any standing on those heels involved, it is always "on"="на".

And you definitely not "ходишь на шляпе" or "ходишь на туфлях", this is weird.

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  • Note that "женщина В туфлях НА высоком каблуке" means again that PERSON is "IN" shoes and shoes are "ON" the heels.
    – onkami
    Dec 22, 2015 at 13:41

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