I didn't really read any of the other replies, but..
These types of threads always get started. I have to wonder if 99% of the time people are trying to fit into skinny/slim/straight legged pants and then claiming their massive legs don't fit?
Dress Pants - Dockers D3 ("eased through seat and thigh") or D4 ("full through seat and thigh") both fit comfortably to me. Granted, I'm not a big guy, but even I can't fit into the other fits using my actual waist size.
Jeans - Express Loose Fit Blake Jeans - these have been my goto for a several years, but finding a non douchey color/finish can be hard. I usually just order online.
I actually just found some new jeans at JCP last week. Lee "Modern Straight", which have a wider leg (but not as wide as loose fit jeans), and a little bit of spandex (1% IIRC) to be a little strectchy. They are advertising as "Active Comfort features extreme range of motion" so I busted out some bodyweight squats while trying them on to test it out.
tldr: LOOSE FIT. LOOOOOSE FIT. quit trying to buy skinny jeans.
I don't have this problem now but when I was around 10 years old I remember having corduroy pants that wore out on the inner thighs . I used to get my clothes at a store that specialized in the HUSKY size. I am 5'11" and about 202. The jeans I find most comfortable are called Duluth Ball Room Jeans.
We shleps praise Duluth baggy pants! Sturdy, baggy, lots of big pockets, everything but fashion.
Really appreciate the info about the Nordstrom Rack shirts, dmw. Hope they actually fit me decently. I've tried everything to get a properly fitting shirt for <$100. I've had so-called slim fit shirts altered, and even had a shirt custom-made by the good people of Asia (it took like 2 months and didn't come out that well). Sometimes I even wear shirts which are too small in the neck with a "button extender" but it looks ridiculous, as you can imagine. The Nordstrom Rack tip will turn out to be a lifesaver if they fit like you say.
I still hate all of you bastards complaining about pants that don't fit. My massive 22's don't seem to cause any trouble even with straight-leg style pants.
...You people can still fit into pants?
I shopped around and looked up manufacturing specs and found the shirts with the largest differential between chest measurement and waist measurement, and the Nordstrom/Rack Trim-Fit were the answer. Having said that, I don't have particularly large shoulders, so someone with more of the "classic V" might still have to opt for the tailored route. It's a pretty standard YMMV situation.
5'8", 240? Have you considered a kilt?
I have a big upper back and neck for my size. I have yet to find anyone that makes a shirt with a 16" neck and a 32-33" sleeve that's not for an enormously fat guy, even if it's nominally slim/trim/tailored/tapered etc...
I needed new shirts anyway, so if I have to live with continuing to have Rocky the Flying squirrel flaps until I burn through 4 more shirts, so be it. If they fit me better than my outgoing shirts, all the better.