Originally Posted by YRR92
Bourbon_basted, I tend to agree. I do think you can start from learning the rules, but then rather than "breaking" them deliberately (a weirdly mannerist form of expression aimed more towards SF than the real world), you can internalize enough of them that you sort of innately apply the thinking behind them. That's sort of what I see from the people who learned how to dress over a number of years, pre-SF -- an undogmatic application of the intentions behind the rules, rather than an unthinking obedience to the letter of the law.
I'll agree that there is a certain mindset that factors into one's ability to learn rather than memorize and regurgitate. I think that has a lot to do with the motivations for wanting to dress "better." (Note I say "better" and not "correctly" because I think it's absurd to say objective rules can be applied to something as personal as style.)
I think a lot of people come here because they want a single answer or are looking for instant gratification. Unfortunately, many that stick around are unable to shake that initial motivation, and take black-and-white queues from senior members under the guise of "learning." Personally I never had this problem. While looking back on how I dressed 5 or even 10 years ago I often cringe. However, I quickly realize that I was on the right track and had the desire to learn. I didn't lurk and eventually join here for the antidote. Rather, I took a vested interest in clothes and the process of formulating a personal style. With that mentality details took a back seat to understanding why I liked something or why something did/didn't work.
These days I generally view individual garments or looks twice: At first glance I let my gut take over. Are the colors complementary? Are the proportions flattering? Does the wearer look comfortable and natural? are generally the first questions I ask myself. If the answer to all of those (to my eye) is yes, then to me you have a good look (even if that means others disagree). However, if even one of those criteria isn't satisfied, then I dive deeper into said "rules" for ways to improve the fit. Again, I fear if your first glance is spent looking for details found on the iGent checklist rather than going with your inherent sense of taste and style, you're doing yourself a great disservice.
In the real world few will consciously notice even the things that I look for off-the-bat. However, these are the exact factors that will lead to someone looking sharp or like they know what they're doing to the casual observer. And for those of us who do revel in the details, satisfying those basic aesthetic principles is all you really need. Honestly, it's not like you're going to stare at a dude on an elevator to see if he has spalla camicia or a 2" cuff... I hope.