I was definitely a newborn in this department, and still very much new to the whole thing. I totally agree with much being said here, and especially with Noelle and Sammy!
Men clothes just aren't designed to be seen, they're more function over form, I feel. Sometimes they can definitely be stylish, but that doesn't even compare to the sheer vastness of women's fashion.
I wouldn't even say I know anything about fashion, or that I'm making the right choices, but I just try to think about what I feel looks good on me.
I had worn 1 outfit before, bought components to make another but today my wife and I went down to a thrift store and tried on all sorts of shirts, blouses, dresses, leggings, pants, capris, etc. And now I have a pretty decent-sized wardrobe to choose from, that...I don't know what to wear tomorrow (lol)
Since clothing for men is more designed for function over form, it really doesn't matter- and it's totally natural and expected to just grab whatever and be done with it. But like with women's clothes, I feel like what I'm doing, who I'm seeing that day, how I feel or how I want to feel, the area, my age bracket, and like anything else you can think of really come into play. It is truly overwhelming!
And like I said, I might not have a good eye for fashion, but as long as you feel good and look good in it, that's all that ultimately matters!