Yes, there are several wearing verbs for different items, נועלת נעליים, גורבת גרביים, חובשת כובע, עונדת תכשיט, מרכיבה משקפיים, עונבת עניבה, these are the ones I can remember now. Other items go with the default לובשת. Not all speakers bother with all of those, some just use לובשת for all. I would estimate that נועלת and גורבת are the most common.
"A" is only used for singular, not plural.
• You are wearing a shoe (a single shoe) • I have a book (again, just one)
• You are wearing shoes (more than one shoe) • I have books (multiple books)
Another option in English is to use "pair", which is a set of two. • You are wearing a pair of shoes (a single pair of two shoes) • You are wearing pairs of shoes (more than one pair)
Things that go in pairs get the suffix -ayim, like yadayim, raglayim, eynayim, oznayim, shinayim, michnasayim, garbayim, na'alayim. Even the day after tomorrow, which is two tomorrows from now is macharatayim (or actually mochoratayim, but anyway everybody says machratayim).