Do forgive me if this has been beaten to death already. However, in following this forum for the last few months, I have come to a conclusion about what attracted me to the 'trad' style in the first place.I enjoy the apparent effortlessness involved--except most of you put quite a lot of effort in to dressing in a particular way.
Much like GHWB I grew up in a family in which it was normal for men to dress in this particular style; plain front trousers, a properly fitting jacket, and a presentable pair of shoes were de rigeur for the men in my family, even after we ceased to have an abundance of wealth. My grandfather certainly had a favorite haberdashery or two, but I never recall him fussing over whether or not his jacket had darts or a rolled lapel. He always insisted that a gentlemen must never try too hard to dress well, because in doing so he was likely to appear pretentious. There's a certain austerity in that statement, I suppose, but that particular ideal is one that many older "WASP" families cherish deeply.
I suppose that what I'm saying is that I find it very difficult to fuss quite this much about what I'm wearing; I prefer a sack cut when I have the opportunity to wear one, but I wore a darted 2b charcoal suit last Friday evening (to a business casual dress dinner) and received a number of compliments. I also don't feel awkward when appearing without a jacket on a day-to-day basis; I enjoy them, but if it's too warm and humid, I'll dispense with the jacket. I wear a tie when the mood strikes, but I'm more comfortable in the heat with the first button of my collar undone.
I wear an OCBD and plain front khaki trousers on a daily basis. They look good; I can meet with students and administrators informally dressed this way. I don't have to spend too much time considering what I'll wear in the morning; I own 14 OCBD shirts, one polo, a pair of loafers, a pair of slip on Sketcher's, and a pair of captoe oxfords. I rarely experience a moment of indecision when the available choices are light blue, French blue, white, ecru, and pink.