I take your point entirely, FNB; however, I would not describe the look against which you caution as “too well dressed.”  Maybe it’s just semantics, but I want always to be as well dressed as possible in keeping with the circumstances for which I am dressing.  Rather, I would describe the look to be avoided as an unnatural perfection.  Your tie example is a case in point:  I always dimple my tie.  Every once in a while the dimple ends up perfectly centered.  I immediately untie the tie and retie it, taking care not to commit the same offense again.  Similarly, try as I might, on occasion after I am fully dressed, the combination I am wearing looks perfectly coordinated.  That’s the time to change some element, often something a simple as my pocket square or my socks.  When my wife, who dresses beautifully in that female way, tells me she likes the way I look except that she does not understand the _________ (fill in one or another article of attire), I respond, “exactly my point.”  It takes a great deal of study to appear unstudied.  I refer you to your own discussion of color combinations that should not work, but do.

My shirtmaker in Rome wears what appear to be custom-made jeans, which fit like a second skin, and with a crease so sharp you can cut sausage on it.  He might possibly be too well dressed, but he is so understated and stylish, he pulls it off with flair.  Raphael made me a pair of custom-made khakis, however I can only hope to one day have a similar level of style.

I popped into Saks 5th Avenue today. It was packed with shoppers, the cufflinks I wanted were gone, and I was asked to help people about 5 times while I was in the Men'd clothes department. Not being one to be rude, I was in the middle of helping someone on with a dinner jacket when the question came up about how long Id worked there. When I said I hadnt (and dont now) the reverse double take of a man being helped on with his jacket by a complete stranger while his arms were half in the sleeves of the jacket (which I was holding) was pretty amusing.

To be fair to me, he did point at me and insist I help him with selecting a jacket.

I wonder if I was too well dressed? I suppose I ought to be flattered that people think i work there.