In all the forums and their respective What Are You Wearing? threads (just a note, FNB Talk Ivy doesn’t get a pass just because they named their thread something different), often the most vicious attack of a person’s outfit is that they are “trying too hard.” The meaning of this put down can change from place to place (what is trying too hard in AAAT might not be for SF), but basically it means that the person is thinking too much about what they put together, and the result looks contrived. It is impossible to label one specific outfit as “try hard” because one person can wear the same thing and pull it off with loads of “swagger” (mainly an SF thing). If you follow these forums (and even some of the blogs) you’ll find the phrase used often. I think it’s bullshit. Here’s why.
(CE - like most of my essay posts, this won’t be an in depth look using sound reasoning with a more suitable option at the end. I just want to rip on some stuff)
(CE - upon proofreading this, I have realized that it is somewhere around 90% sarcasm, so don’t take anything too seriously. Those things that are particularly sarcastic [and which I don’t want to be mistaken as serious] are marked with a “10” to show my sarcasm meter level)
If trying too hard is the worst thing a person can do, then it follows that not trying at all is the best thing a person can do. The goal here is to be able to put little to no thought into what you will wear, and still come out smelling like roses. The practitioner of this style of dress will look great even if they have a slightly rumpled look or things out of place. Many call this “sprezzatura,” since anything Italian is automatically stylish (10). Some hallmarks of this quality are: button-down collar buttons left undone, screwed up collars in general, one shoelace left untied, tie tucked into trousers, wrinkled shirt but pressed suit (or the other way around, or both), cuff buttons left unbuttoned, etc. etc. Basically what would be sloppy on a non-initiate looks fantastic on the well-schooled dresser (or the poster with higher than X-number of posts, which doesn’t mean the same thing regardless of how often it is taken to be). The rule is, as Cary Grant or Clark Gable or Clark Kent or some other guy whose name starts with a C said (10), you should learn all the rules of dress and then forget them.
The problem is (oh yes, there is a problem), that someone who learns the rules will not forget them. They might choose to break them (here I am, wearing an oxford woven shirt with a suit!) here and there, but they still know them (how can you know you’re breaking a rule if you’ve forgotten what the rule is?).
The other problem is (well I guess there are more problems) that all those hallmarks of sprekkenzitura don’t come naturally to those who know the rules. And all those who try to introduce those elements into their outfits know the rules (Phat Guido, anyone?). So if the rule knowing dresser consciously leaves his pants unzipped in an attempt to appear nonchalant, he is quite obviously trying. Because he thought enough about his outfit to think it would be improved by that little detail.
Here’s the main point (finally), the reason the “trying too hard” label is garbage. Because the good examples people use to prove their point (like Phat Guido on SF [who is an excellent dresser], 1966 or Moose on FNBTI, Patrick on AAAT and TC, and many others) really do think about stuff, and try. And no I can’t say for sure because they are their own people, but the details of their outfits prove to me that they do think and that they do try.
So saying someone “tries hard” like it’s an insult or a criticism is strange because all the best internet dressers (sounds like an oxymoron if I’ve ever heard it) try really hard. And they look great all the time. Imagine if someone really didn’t try hard at all. It shouldn’t be that hard to imagine since they’re all over the place. Guess what? I don’t find them particularly stylish. And I’ll bet you don’t either.
The real problem with people who get the “try hard” label is that they are often new to a style. Once they get used to it and learn more (and try more) they will gradually start looking more comfortable and better. Hell, go look at some of my old WAYWN posts on The Curriculum. Actually, don’t, they suck. I look terrible. I’m surprised they didn’t kick my ass out after my first five posts. But I feel like I do a better job now, and while I don’t consider myself particularly well dressed in comparison to some guys out there, I look and feel a lot better than I did back then (10). And all it took was a year and a half.