I personally hate loose kind of jeans, just shapeless.. Shirt could be looser tho'. And while it's not a rocked science, like 85% of guys I see every day are far from figuring it out somehow (getbiggers are hopeless.. Skorp comes to a mind like one who has a sense for a style, but that's an exception).
To be honest, Ive never understood the strong urge to have "style." I mean, sure, if you're a businessman you're going to have to look very presentable.
Obviously, its good to look nice. I always look nice when I go out. Im not fancy, but I look nice enough to where its not an issue, either at work or in my personal life. As for my job, I am not required to wear a suit. Heck, I can go into work with jeans and a polo shirt on and Id be okay. Anyway, you can look nice and presentable without going overboard.
You make it seem like men have to "figure out" how to dress, as though its some huge accomplishment. Sorry, I just don't spend that much time trying to "figure out" style. Its a VERY SMALL issue/problem in my life. I dress nice enough. Its never been a problem. I do not understand why I need any thing more than that.
And lets be honest here, I can buy a $20.00 pair of jeans from Old Navy, remove the Old Navy logo, and put an expensive logo on them, and 99.9% of people would not know the difference anyway lol.
Just my 2 cents.