The following is a list of English examples of "transgender" occupational bynames - bynames where the occupation modernly, or pre-modernly, was associated with one gender or another, but where you find women bearing the masculine form and men bearing the feminine form in period. I've also put in plain descriptives, where the word has a masculine meaning, but is used by women. This list was cobbled together without any regard for completeness, and any feminine name after 1350 that doesn't have the definite article may be an example of an inherited surname, and not a literal descriptive. Forms are groups by header name, and listed by date. All derivation notes are from Reaney & Wilson.
Abbess
Jamys Abbys 1524
Richard Abes 1524
"Possibly OFr abbesse 'abbess' used ironically."
Arlott
Muriel Arlot 1279
"OFr herlot, harlot, arlot 'lady, young fellow', found in English as a masculine noun in the 13th C in the sense 'vagabond, beggar, rogue')."
Copper
Juliana la Copper 1275
Bartholomew, John le Copper(e) 1327
"In the 12th C, copere is certainly a variant of cupere 'cooper', found late as copper, but it may sometimes be from OE coper 'copper'. The short vowel is clearly evidence in Copper above, 'a worker in copper'."
Sewer
Richard le Sewer 1279
Margery Sewer 1327
"A derivative of OE s{e-}owian 'to sew', a 'sewer, tailor'. The feminine form survives as souster."
Shepard
William Sheperd 1279
Henry Sephurde 1296
Emma le Schepherde 1279 (note masculine article le)
Alice the Schiphird 1303
Avice la Scheperdes 1311 (note feminine article and feminine form)
Webster
John le Webestere 1275
William le Webbester 1284
"OE webbestre 'female weaver', though usually used of men."
Source
Reaney, P. H., & R. M. Wilson, A Dictionary of English Surnames (London: Routledge, 1991; Oxford University Press, 1995).