My boss has been wearing the same things for decades. Seriously, decades. Only once or twice have I really questioned an article of clothing (you've had that for how long? When exactly was that fashionable?) but for the most part I realize that at the end of the day, when I leave the office I could no more tell you what she wore that day than tell you how many times I blinked.
I was really influenced by this article by Eric Wilson that I read a few months ago in the New York Times. The gist of the story is a challenge by this website to choose 6 items from your wardrobe and limit yourself to them for an entire month. 30 days. 4 weeks. Accessories are fair game, though, and you can wear as many different pairs of shoes as you want. Most of the women choose black: a skirt, pair of pants, blouse, jeans, and then maybe a tshirt and a versatile sweater or something. As crazy as it might sound, a lot of women are okay with their chosen lot in fashion life and surprise surprise, hardly anyone notices that they're wearing the same thing over and over. I think I've achieved this without even trying at work. I rotate mainly between 3 pairs of nice pants, depending on the season, and two or three skirts. My shoes are either brown or black, and if I gave myself 15 seconds I bet I could only come up with 4 shirts that I wear to work on a regular basis.
Therefore, not only should dressing be easier than many of us make it, dressing up should certainly be easier than I tend to make it. One thing that strikes me when I think about the Six Items or Less (shouldn't it be Fewer? I digress) is the allowance for shoes and accessories. For goodness sake, my boyfriend is 6'4" (or close), I should wear better shoes. I'm allowed to be as tall as I want around him. Also, accessories. I could do better with those. Talk about multiple ways to wear one shirt - all you need is different jewelry every day and nobody is going to notice that you haven't changed your shirt all week, especially if you still smell good.