Dressing in traditionally feminine outfits (dresses, heels, makeup, etc) is a choice that only men can actually freely make. Men do not face oppression for refusing to adhere to femininity, women do. Women are still persecuted at work and home for not presenting feminine enough. One survey found that more than half of employers would be less likely to hire a woman who didn’t wear makeup, and admitted it would also have a detrimental effect on her promotion prospects.
Donning the shackles of another’s oppression for fun is the very height of privilege.