Said it elsewhere, will say it again -- a case can be made that it's more stereotypically feminine to be sentimental about one's manhood. And more stereotypically manly to be utilitarian about it and wear the clothing you need to be comfortable without indulging wishy-washy feelings.
Not saying that this should be the rule, mind you. In fact my point is that aren't any rules. If protag wants to be a man again, they can start by having a bit more faith in their manly spirit. If it's there at all and not just going through the motions like so many guys do.