Oh yeah, that scruffy look is by far the most appealing look to women, going by statistics. I wonder if that's just the current fad, or if women would have said the same thing like back in the '60s or whenever. I remember my high school girlfriend's dad telling me a guy should be clean shaven to have a more professional look.
Everything and anything that signals that a man is successful, sociable, healthy, etc... will be trendy. During the 90's (my highschool years), people who were successful, sociable, etc. (basically, had the qualities that women wanted) were clean shaven. Most good jobs required men to be clean shaven. It took work to be clean shaven. It was a mark of "superiority". However, as time moved on, being clean shaven was an easier task... it could be done by everyone. Also, almost all companies, even those that were not prestigious required people to shave. The razors became cheaper and more efficient (electric shaver, etc.). Shaving became less of a mark of success.
I still remember the consternation of the American public when they first saw US special forces wearing beards, having long hair, etc. during the 1st gulf war in order to mix in with the population. To be honest, I was shocked also. They were professional soldiers, they were suppose to be clean cut - what are they, hippies??? As these soldiers came home, ,most of these men decided to keep the beards, etc.. Then slowly, the beard and facial hair started to be mainstream. Those people who had good jobs, their companies allowed them to dress down (no more suits); some of the employees who were very important to companies... Well, those companies allowed these employees to have beards, etc... Then there was a switch. People who were extremely successful, who were important to their companies. A lot of these people had beards because they really didn't want to bother with shaving (perhaps they also liked the aesthetics?) and as they were really important to their companies, their companies allowed them to have facial hair. Beards started to become a marker for successful people. Those that shave or continued to shave, basically those people were not important enough to be allowed NOT to shave (block buster employee??? kmart employees, etc.), .
Anything can be trendy as long as it signals attributes that women what. Remember facial scars use to be a thing. It would still be a thing if the upper class, successful, social men continued to do it. But they don't so its not really a thing any more.
Remember
https://en.wikipedia.org/wiki/Dueling_scar
You don't mention your age when you were the first person in your group to have the five o'clock shadow. Maybe you grow one better now? I notice my facial hair comes in a lot more fully now than it did when I was younger.
I think I was around 38 when I stopped shaving every day or so. I'm 47 now. I do shave but probably once a week. I let it grow out for a week or so then I shave it all off; I'm lazy. It's awesome because my beard grows out in the same pattern as iron mans beard. I use to be conscious about how my beard grew out before the marvel movies. I still let it grow out because, hey, that's my natural beard. But now, it's like, man, not a lot of guys can have iron mans beard hahahahahahahaahha
At the end of the day, these markers are not important. A lot of times, how one carries oneself is a lot more important. If you are what women want, you will naturally give off those markers. Those dueling scars.. was it about getting the women? No, it was about how successful you are. You bravery, fraternity with other successful men, etc.. The first people who started those dueling scars, they weren't doing it for the women. They were doing it for themselves...