“Being chic isn’t about following trends, it’s about setting them.” – The Chic Spy
Women have always been adept at high/low dressing. We know what this is. You may not be familiar with the catchy name, but once you understand you'll probably roll your eyes and say 'oh, that. I've been doing that for years.'
High/low dressing is simply putting together elements that are from different ends of the 'status' (read $$) spectrum. The Chanel purse with the wife beater from Target. The Christian Louboutin shoes with an armful of 'vintage' lucite (plastic?) bangle bracelets from ebay. You get the idea. Putting together things that you like together regardless of the perceived value or status of the various…variables. I had an instructor in college who used the term 'jamming'- meaning to put seemingly incongruous items together, items which have very different 'meanings' attached to them. Similar sort of idea, but the possibilities are more extreme. I see high/low dressing as simply putting things together based on the visual appeal, and jamming as meaning a more pronounced, aggressive approach- visually or conceptually.
Used to be that when doing the high/low, one would do one's very best to disguise the fact. Bargain basement purchases were nothing to be proud of, and certainly not to be worn with the intent of making a fashion statement. Maybe there were a few brave souls who indulged, but I'm pretty sure they were considered eccentric to the point of mental unbalance.
The first time I'm aware of it being considered acceptable in the mainstream was at the 1998 Oscars when Sharon Stone wore a long, silk, Vera Wang skirt with a white button down shirt from Gap. I would imagine there are other examples prior to this- I don't know- I'd love to hear Tim Gunn on the subject. (His new book is coming out soon. I have a pre-order in, of course.) Now examples of high/low dressing show up regularly in fashion mags, red carpet events and everywhere the rest of us regular folk congregate.
Back before it was stylish it was done, one assumes, out of economic necessity. Nowadays, if one does it with great confidence it doesn't look like an effort at economizing. To make it work as a fashion statement it must be done almost flamboyantly- make it almost more of a 'jamming' thing than your basic high/low dressing. One of the most important parts to making it work is not making any effort to make anything look like what it isn't; in other words, don't try to pass of a 'low' item as anything other than a 'low' item. If someone figures out that you're trying to pass a cheapie item off as some sort of 'couture' thing, the gig is up- and your credibility is shot to hell. Better to just wear it with a total 'tude- stare them down as if to say 'yeah, I got a vintage YSL purse paired up with my Kmart sweater, you gotta problem with that??' Not only is your credibility safe, but you may find you get more respect due to your obvious courage, and dashing sense of style, darling…
To me, this is the same as comparing what is considered classic beauty with that which is quirky and unique- both have their value and both are valid- but for me, the quirky often has more potential for personal expression and thus the potential to be far more interesting.