Depends on his circles. Harry Styles was considered sexy for wearing a dress and there was famous men that have pull it well at different red carpet. At conservative circles it would go bad.

Same with metrosexual men. David Bowie weared make up and was hot. Many rock stars wear make up, including some heavy metal musicians that are incredibly successful with women. At least the more progressives.

But with conservatives, it is frowned upon.

At the end of the day, if you want to break gender norms, you would need to take a risk. But there are several transgresive men who have shown that wearing make up or dresses can be sexy and have been really successful with many women (and sometimes with men too).