What I mean is: if the person wearing the pants assumes a masculine/dominant role, then can we say someone assumes a feminine/submissive role by saying they wear a skirt in a relationship? Especially if they were not given a choice and have to accept their subordinate role?
Is it possible in English? It's not my first language and I would appreciate the comments.
Best Answer
As I noted in a comment above, I would be avoid using either expression because both are based on outdated and potentially offensive stereotypes of gender roles. In his answer, David M provides a nicely nuanced account of the issues involved for native and nonnative English speakers alike.
Historical Antecedents of "Wears the Pants" and "Wears the Skirt"
The earliest instances in English that use of reversed clothing choices as a metaphor for reversed gender roles involves not pants and skirts, but breeches and petticoats. The playwright Richard Brome wrote a comedy circa 1629–1632 titled The City Wit, or, the Woman Wears the Breaches. Wkipedia's article on the play asserts that the alternate title "the Woman Wears the Breeches" refers to a male character who disguises himself as a woman but continues to wear trousers beneath his skirts. However, the play also features "a shrew and harridan"—the mother-in-law of the main character—and her browbeaten husband; so the phrase "the woman wears the breeches" may be a double entendre if the later meaning of the phrase already existed in 1632.
That meaning clearly existed 20 years later, as the next-earliest reference in a Google Books search establishes—an epigram in John Mennes, Recreation for Ingenious Head-Peeces. Or, A Pleasant Grove for their Wits to walk in (1650):
The next occurrence appears as a comment attached to a (rather impenetrable) proverb in James Howell, Lexicon Tetraglotton, an English-French-Italian-Spanish Dictionary ... With Another Volume of the Choicest Proverbs (1660):
Richard Saunders, Saunders Physiognomie, and Chiromancie, Metoposcopie, the Symmetrical Proportions and Signal Moles of the Body (1671) purports to have discovered a physiological indicator of uxoriousness:
And John Dunton, Athenian Sport: Or, Two Thousand Paradoxes Merrily Argued to Amuse and Divert the Age (1707) volunteers this gloss on what it means for a woman to wear the breeches:
"Wears the petticoat" as a counterpart to "wears the breeches" first appears in Joseph Addison, The Spectator, no. 482, (September 12, 1711), in the guise of a letter to the paper:
The earliest occurrence in a Google Books search of "wears the trousers" (rather than breeches) in reference to a dominating wife appears in a joke published in Life magazine (September 19, 1889):
And the earliest relevant Google Books result for "wears the pants" in that sense occurs in J. S. Robinson, "Women Who Seem Men," in the [Salt Lake City] Young Women's Journal ("Organ of the Y[oung] L[adies'] M[utual] I[mprovement] Associations") (December 1895):
Louis Menand, Miscellaneous Documents on Divers Subjects (1896) says that the saying about pants and petticoats was originally French:
Pants versus petticoats again appears in Handford Lennox Gordon, Laconics (1910):
And again in Florence Guy Woolston, "Albertism," in The New Republic (December 14, 1921) :
The earliest instance of "wears the skirt" (in the relevant sense) that a Google Books search finds is from The China Critic, volume 7 (1934) [snippet]:
"Wears the Pants" versus "Wears the Trousers" in British and U.S. English
Tristan R points out in a comment beneath the poster's question, "wears the trousers" is more common than "wears the pants" in British English. An Ngram Viewer chart of published British works in the Google Books database for the period 1850–2000 seems to confirm his observation, though the difference is not huge:
The corresponding Ngram Viewer chart of usage in U.S. publications shows a clear preference for "wears the pants":