Orphaned/Headscratchers/Clothing

Why on earth is it such a big deal for men to dress up like a woman if they feel better that way? Women can wear virtually anything a man can without issue, but if a man wants to wear women's clothing, people get all freaked out and suspicious. Double Standard much?
 * Women wearing men's clothing used to be scandalous, but this has been more or less completely eroded by the progress of women's rights - wearing clothes that should be for men only was an easy way to make a point about how you should be able to do anything men can, and the more women did this the more normal it began to seem. There has never really been a significant "men's rights" movement, so the taboo is still strong in the other direction.

Why is it so hard to find a good tank top these days that doesn't show 50% of your cleavage? They even do this for the little girls. AND THEY DON'T EVEN HAVE ANYTHING YET.

When, exactly, did we human beings start wearing underwear - and why? I mean, it's not like we need it. There's no disadvantage I can think of to going commando. And the "hygiene" argument doesn't really explain anything. Sure, with undies we keep our outer clothes clean on the inside - but then we get the undies themselves dirty. That just makes for twice the load of laundry, which is a waste of time, money, and water. Does underwear date from a time in history when outer clothes were very rough-fibered and we needed to keep from chafing? Is it what we exercised in before shorts, tank tops, and spandex were invented? Or did we just want to make the art of the striptease even sexier than it already was?
 * I know in the middle ages, outer clothing wasn't washed as often as modern standards would require -- they'd just be brushed and hung or folded for the next wearing. "Body linens" (shirt/drawers for men, chemise for women) were worn to protect the outer clothes from body oils and dirt, and could be washed more easily. This is also where the tradition of white underwear came from; when you're boiling your laundry with lye soap, plant-based dyes are going to lose the battle.

Ties, neck ties, bow ties, just ties....why? they server NO purpose what so ever, but your always supposed to wear one if you want to look professional. By doing something that has absolutely no reason at all, you somehow prove that your mature and responsible. (Doesn't help I start having panic attacks whenever I get anything wrapped around my neck)
 * Ties, etc., "evolved" from scarves. Scarves slowly changed into the cravat, which got thinner and became the tie. It's useless, yes, but traditional, and it used to be useful.

Here's one: why are those damn Che Guevara tee shirts so popular? Especially amongst those who know next to nothing about the man or what he did or stood for? (Hint: watching "The Motorcycle Diaries" does not make you an expert.)
 * This troper once saw a poster that said "Even though you spend your whole life fighting the forces of capitalism, you still might wind up on a T-shirt sold in a store owned by the GAP. Irony?

Why does looking for a great pair of pants have to be a pain?

Why can't someone just make a fasionable-yet-functional unisex jumpsuit?!
 * We wouldn't have anywhere near as much vanity, no self-appointed "fasion police", and no jagoffs telling us our colors are off!
 * "Fashionable" and "unisex jumpsuit" are a direct contradiction. Society tried it in the 1970's and hasn't quite recovered yet.
 * And is it really so bad to put a little bit of effort into looking nice? We're not talking about fashion here. Also, in your scenario, there would have to be actual fashion police to enforce your shitty jumpsuit program.

The current fashion trend of all ladies' shirts and dresses being baggy and shapeless is just hideous in my opinion.
 * I get it, you're going for the bohemian look. You either have to be a twig or fat enough to fill out the shirt to wear that stuff. Anyone else (ahem), it looks like maternity wear. I always have and always will prefer form-fitting clothing. I'd rather show off my curves than wear a glorified trash bag. Hopefully with this new decade, comes a new fashion trend.
 * Hey, it's a lot more comfortable than skin-tight stuff.
 * This troper disagrees, skintight stuff is awful. Most people aren't twigs, so you just get to see all their rolls of fat. Plus it's uncomfortable, particularly in a Queensland summer. What bugs this troper was the recent trendy winter clothing. Tight skirts and lots of frilly blouses with puffy sleeves, all in a range of shades of grey. Urgh.