I've been thinking about image lately, not sure why (might have to do with my incredibly desperate need for a haircut), and the Smart Set articles offered some interesting points but all the advice and history doesn't change my complaints. There are several reasons I don't wear make-up or worry about my clothes too much.
One reason I don't wear make-up is I haven't found a foundation I like; Honu-Girl and Sarah have pledged to drag me to the Mac counter and solve that problem. Another reason is I regularly have one or two of the pimples that make-up only makes look worse, so why bother? Another reason, the five minutes I might spend putting on make-up could be spent sleeping; I don't think anyone has a way to get around that. Then there are all the social/emotional/political problems I have with make-up, which can be boiled down to, "why isn't my face good enough?"
Part of the reason I don't much worry about my clothes is because I'm hard to fit. I'm taller than average and so have broader shoulders, longer arms, longer rise, longer legs, longer torso, and longer fingers and feet, than clothing manufacturers seem to think I should. If you want numbers I posted them here.) I do alright with pants; they've caught on that taller women often need a longer rise as well as longer inseam. But blouses just don't fit. I don't know of any "tall women's" stores around here. There was one at Tyson's Corner but I wasn't tall enough for their clothes, at least not in high school, maybe now that I'm not so skinny I could find stuff there (and I traveled several hundred miles to shop). And no one seems to make tall fat women's clothing; I not that fat but I'm bigger than the largest "tall" size in store and catalogs I've seen, at least for tops, if they carry tops in talls. I like mens shirts - no shape, but they reach my wrists and don't pull at the shoulders. Besides dressing to look nice takes effort and thought (and enthusiasm*) that I have a hard time mustering first thing in the morning.
On the flip side of the coin are all the social/emotional/political pressures that boil down to you'll never get a man looking like that.
*An example of how little thought, effort, and enthusiasm for the morning I have: The stubble on my legs can grow so long it bothers me in pants and I will still forget, or run out of time, to shave my legs during a 45 minute shower. (Most weekday morning showers aren't that long, 10-30 minutes.) This isn't uncommon, unless I'm swimming regularly.