I'm trying a bunch of styles but even men's skinny jeans are too loose in the thigh. I can't tell if this looks okay or sloppy.

Has anyone found any pants that work for them? or do you just get them tailored? How do you know if they look sloppy or if they're fitting right? What are the unwritten rules of manpants?

I've actually managed to find a lot of pants at Value Village lately. It depends on how they fit and I usually find that the more expensive ones (for VV anyway) have the better fit. I basically go by what I think looks good. My main issue is the hip area. I don't want it to flare out and make me look like Tweedledum, so if it fits around my butt and hips nicely, I tend to take them.

Levi's 514s work for me. They have a bit more room in the butt but don't balloon on my thighs.  I have athletic thighs so YMMV there.   Levis 513s are even tighter on the thighs while giving that extra bit of butt room.

It is becomming more difficult to find men's casual pants, shorts, etc. that fit properly. Most have become way too loose and baggy to feel comfortable.

Chinos are always a nice pair of pants, and you can get chino shorts as well. Otherwise, the youth shops are coming out with these really stretchy shorts and pants, the pants are like drop crouch joggers, but look like denim. There's a bit of extra material on them between the legs that like.. isn't usually there. Kind of makes them look like jodhpurs in the front.

I don't remember what chinos are, or if DangerTom cares anymore, but what I wear depends on the situation. For everyday life, I usually wear denim pants from various free bins or dumpsters. Sometimes I hem my pants or purchase them from thrift stores.

My personal rules for pants are that I want to strike as reasonable a balance as possible between being respectable/professional and being visibly lower class. I try to look poor and uninterested in fashion except where it helps to wear khakis or brown/black pants and act like a businessperson.

Your clothing choices should be driven more by personal preference than gender - if you feel good and confident, you will always make a better impression than if you wear the right stuff and feel bad. When I was living as female I often went to interviews wearing clothing that people told me was appropriate, but I always did better when I gave up and wore clothes that fit badly and felt right.

I think if it doesn't matter you should wear what you want, and if you care much you should seek out a tailor. You likely don't have typical dimensions and wouldn't be wasting money by making sure your pants fit well.