I think a lot of men here really aren’t appreciating the sheer variety found in even ordinary women’s clothing. A man can pick out work pants, and they may be khaki or pinstripes, but for the most part they will cover the same parts and be a suitable fit for the work. Likewise, he may wear polo shirts or button ups to work, but within these the variations are minor (slim fit or standard? button down or not?), and with few exceptions they will all be acceptable to wear to work. Basically, when men pick out work clothes in their size, they know they are suitable for work.
I have lots of clothes, and I can’t even think of two shirts that I own that have the same neckline. My button ups range from matronly blouses to button popping club wear, but most of it is in between. Furthermore, retailers are not consistent in catering to the work-appropriate crowd, and the few store that do it well are on the higher end ($70-$120 per item, and even they often put the hemline a little too high or the neckline a little to low.
And then there are body types. I have wide hips, which can make a prim shift dress look nearly obscene. A big chest likewise looks provocative in what other would classify as conservative tops. And bodies change, especially with pregnancy. But they also just change through the month. Heck, even something like wearing tights can change if an outfit is appropriate or not. More than once I’ve greeted spring in a cute dress I’ve worn all winter, only to realize halfway to work that it’s too much with bare legs.
And that’s just a lot of stuff to balance. We can’t look matronly or prudish, but we can’t look too sexy or provocative. But we also need to project power while looking feminine but not too young and not too old. And fashionable without being too trendy.
And that goes for a dozen moving parts- makeup, skirt length, jewelry, undergarment lines, shoe height, strap width, etc. All of this crap needs to straddle a fine, nebulous line that we have to calculate basically from scratch every damn morning. And at six in the morning I have limited brainpower for any of this. So yeah, miscalculations (and sometimes a heap of “screw it, I’m putting on something clean and leaving.”) happens.