Quote Originally Posted by GBREAL View Post
I still don't get it. I guess its one of those things I'll have to put on the shelf and take it out later.
It comes down to philosophy and psychology, I think, in that there is nothing to "get." One cannot fake comfortableness and confidence which is the essence of nonchalance. You are either confident in how you look and feel or you are trying to be so which shows in many ways. Dress the way you want to dress, do it often, and you won't even notice that you are nonchalant because you are naturally nonchalant. No matter what you do and how you feel, people will have differing opinions on your style, thus differing opinions on whether or not you look nonchalant, sloppy, weird, dapper, etc. Some people associate pleats and suspenders with funny old men, others fedoras with corny detective stories, others wide lapels with Disco. For the sake of your happiness and sanity, dress to please yourself (within reason) and forget about anything else (I say this not intending for you to wear pajamas to a formal event because I still believe it is good to follow etiquette, though slightly modified for taste, in situations).

Take sproily's black-tie photo for instance. That exploding pocket square makes all the difference, in my opinion, because it says "Yeh, so I had to pull out this here handkerchief for some reason and don't have the ability or desire to stand in front of a mirror to repack it all nice and dainty like one expects for black-tie. What's it to you buddy?" That is nonchalance and uniqueness. It might not suit some people, but it apparently suits him (and me too).

Quote Originally Posted by Otateral View Post
If there's one thing I would like to stop doing is constantly having to adjust the cuffs on my shirt, so that they don't stick out too much or too little from my jacket sleeves. I think a bit of shirt tailoring would fix it though.
I've often wondered about this predicament and have come to the conclusion that no active and practical wearer of suit jackets or sports jackets with long-sleeve shirts is able to maintain an equal and adequate amount of visible cuff. All of my shirt sleeves have bee tailored for me and my jacket sleeves have adequate wiggle room, but one or both of the cuffs still either disappear or sneak out too far during normal activities like opening doors, getting into a car and fasten a safety belt, reaching for something, digging into my jacket for my wallet, etc. French cuffs seem to be the most problematic for creeping up or out of the sleeve and finding a natural riding position with the wider cuff and cufflink to catch. So in essence, I think all the vintage movies, advertisements, and the like that we see with men in immaculately even visible cuffs involved time fussing with the cuffs. I suppose if one were to never move his arms much and never reach he could maintain that look, but I cannot seem to. Then again, maybe there is something wrong with my jacket and shirt sleeves?