Those of us who regard style as self-expression like to think we dress for ourselves. Yet even so, we are dressing with the understanding that we will be seen and in being seen, convey a bit of who we are.
A couple of recent posts over at The Sartorialist (and some of the follow up comments) really highlighted some of the divergent ways people approach this issue. On his post from Friday, 11/23/07, "A Less Narrow View", Sart says, Often I read comments on this blog like "Shouldn't clothing enhance a woman's form and femininity? " or something of that nature. I think this is a very narrow view of what clothing should/could do for a person. Clothing only needs to keep you protected from the elements, past that what you do with them is your option. This young lady is a great example of self-expression and intellectual dressing.Nothing she is wearing really speaks to WHAT she is physically ( fat or skinny, tall or short, male or female) but her look speaks volumes about WHO she is mentally.
I love this distinction he's making. Do we dress for our bodies, or do we dress for our heads? It's the whole philosophical body/mind duality issue writ in fabric. It's often assumed that women's primary motivation with regard to style and appearance should be to "enhance their form and femininity"* and strive to achieve an appearance that conforms as closely as possible to cultural standards of attractiveness, and many women have subscribed to this concept. (And going to extremes, there are actually people who espouse the notion that it's a woman's obligation to look as attractive as possible.) Watch any daytime talk show or "makeover" shows, or read through most style books and the predominant view is that style is all about the body. Accentuate the positive and eliminate (or camouflage) the negative. The result often is a closet full of clothing devoid of any expression of the personality of the wearer.
At times I think we women (and I include myself in this) can get so hung up on what is "flattering," or that which most closely conforms to the thinner/taller/younger cultural ideal that we inhibit the self-expressionistic component of style**. We all want to look our "best" but that isn't always about what clothing accentuate our waists and makes our legs look two miles long. I grew up believing that the Clothing Prime Directive was One Must Wear Only What Makes One Look Thinner. I still have a tough time letting go of that, even when it means passing on something that otherwise really speaks to me.
I don't think the answer lies totally abandoning those cuts and styles that fit and flatter, but rather that we look at style as serving who we are not just physically but creatively, emotionally and mentally, and that we don't subjugate all sartorial self expression to Pretty Über Alles. Finding that balance is where style becomes art and inspiration. What makes us look "our best" often means incorporating both elements that enhance our physical selves and those which express our personality, even if it would make Tim Gunn cringe.
*Walk around Newport Beach and you see a multitude of women who have subscribed to this viewpoint, a bland cookie-cutter army of extremely slender, mostly blonde, designer-jean-clad trophy-wife-bots. It's a look almost devoid of any individuality.
**Of course, I did get into dog-with-a-bone mode in comments on one of his subsequent posts about why curvy, petite women don't want to wear double-breasted jackets, but I'm nothing if not conflicted.