A couple generations ago dressing down used to have negative connotations. It meant dressing below standard, below what was even considered appropriate for casual or sportswear. It was so onerous that the last thing you wanted to experience from a parent or your boss was a "dressing down." Nowadays, dressing down pretty much means avoiding at all costs anything resembling good taste, especially anything tailored, such as a suit (men's or women's), or a blazer and slacks, a dress, or a skirt with a co-ordinating blouse. Dressing down is a by-product of the 70's/80's commercialisation of the 60's free-speech, anti-war, "it's-not-what's-on-the-outside-but-what's-on-the-inside-that-counts" movements. This, of course, brings us to the idea of "casual Fridays;" which is little more than an excuse for not wanting to look like Gregory Peck in "the Man in the Grey Flannel Suit." A look I don't necessarily see as pejorative.
The movie "Good Night, and Good Luck," made a strong impression on me. For those of you who haven't seen it, it takes place at the CBS studios in New York during the early 50's. What impressed me (beyond David Straithairn's uncanny realistic portrayal of Edward R. Murrow) was the setting. More precisely, how people dressed in that setting in that time: the men in their dress shirts and ties, and women in A-line dresses or skirts and blouses with mostly collar and stand or peter pan necklines. Now granted, this was an office environment in the news division of a major network; and yes, there was a sameness, an overtly conformist look (emphasised by the black and white cinematography); nevertheless, the setting was not atypical of the standard office environment of the time. The point is, they looked professional – people serious about their work and dressed accordingly.
Ideally, I suppose, the world would be better if people weren't judged by what they wear, or how they maintain their hair, or how they smell and other aspects of personal hygiene – hmmm. Anyway, such are not the ways of most highly developed cultures. And since our society thrives on the visceral, what we wear is one of the primary determining factors in the way we present ourselves; it tells others a lot about how we wish (or, more accurately, how others think we wish) to be perceived. That includes all manner of dress, whatever the circumstances. Whether we like it or not, what we wear makes a very powerful initial – visceral – impression.
Dressing down is just that; dressing down. It's a symbol of lowered standards; standards society has come to accept as the norm. It reflects the cavalier attitude that recent generations have fostered toward the imprecise, the unclear, the inexact. We no longer focus our attention on one or two tasks and endeavour diligently to assure their veracity. No, today we multi-task, which is a euphemism for companies to overwork and under pay employees so as to achieve what can only be at best the bare minimum. As long as we get the job done. Whether it's done well is really not the principal concern today. Businesses supposedly can't afford the time and cost of some one concentrating single mindedly on only one or two projects and doing them well. We proclaim the need for and supposedly value excellence; but, we really don't have time for it. We can't afford it. Yet, for some reason we have lots of time and money to redo the job again and again until it's right; that is, until it's "good enough." I use general terms because this issue of multi-tasking is endemic throughout our society. It does not matter whether the work involves manufacturing or supplying a service; multi-tasking, cutting corners, is pervasive. And it's reflected in how we dress. Treating your appearance seriously is no different than treating your work seriously.
Oh, I can hear it now, "I don't need to get all dressed up to do my job well." Theoretically that's very true. But, dollars to donuts, reality dictates the opposite. Unfortunately, as Kevin stated, the sin of it all is that when you don't know an higher standard you don't know you're lacking it. If the standard of dress is slovenly, well, I guess that's "the style" and we're supposedly no worse off for the lack of knowing any better.
Unfortunately, there is no surprise to any of this. After all we are a society driven by what is commercially expedient; and the key to commercial expediency is the lowest common denominator – what has become referred to as "Pop Culture," in which charlatans like Andy Warhol, Cy Twombly, Laurie Anderson, Meredith Monk, John Cage, Terry Riley, John Galliano and John Gaultier , and any street thug who spews violence laden profanities to a back beat are lauded as geniuses. Who needs to learn how to draw? Who needs theory and counterpoint? Who needs talent? Evidently nobody these days.