A rundown on some Black Friday pants and their skateability... Thanks for all of your advice in this thread, helped me figure out sizing.
Levis 541 Athletic Taper (Stretch) - They're essentially relaxed fit pants at the upper thigh and above (maybe a bit of a dropped crotch?), and a tighter tapered fit at the lower thigh and below. Definitely not a relaxed fit pant at the knee like I was hoping for.
They don't resist movement or twisting, which makes them really solid for skateboarding. However, They are slightly tight at the knees (but it doesn't affect movement when sized up in length). Err on the side of sizing UP the inseam, as that seemed to help the knee tightness and pant mobility more than sizing up the waist. There was some mobility issues with ones that are true to size length, even when sizing up waist, but again more length solved both issues. The potential extra length isn't as huge of an issue due to the taper, especially while wearing shoes. Feels like a slim/tapered fit at the lower thigh and below, but with a comfy upper thigh/butt/crotch area.
The 541 is not most comfortable fit overall since it IS going for that tapered look down low (unless you like the feeling of tighter pants, of course), but its only really uncomfortable when sitting. They look pretty cool to me, way better looking than straight pants but are more comfortable than purely slim jeans. Less unruly than relaxed pants due to the openings staying above your shoe. If that all sounds appealing to you, they skate and move very very well.
A cautious recommendation on the 541 fit (a bit tighter than I imagined), but a really solid recommendation on the cotton/tencel-lyocell/elastaine stretch material. Definitely look into getting that material mix on whatever looser fit you prefer but I don't think this mix is offered in many looser fits sadly.
Levis XX Chino EZ Waist Standard Taper (Stretch) - These things are really soft and comfortable and almost loungey. Feel pretty high quality, but I'm not sure the material will stand up to a ton of skateboarding (not ripstop weave or anything). They are like a thicker Polar Surf (except they actually have a belt loop). The fit is a bit less dorky too, they look nice.
They don't get in the way of movement. Great to skate in. The EZ waist is really comfortable, not just a more generic elastic waist like some other pants.
Almost feels like a lazy around the house pant, but looks good enough for slightly formal wear. Doesn't look like an elastic waist pant in that regard. A slightly relaxed fit with only a slightly tapered end, which I really like for skating. Not tight at all, like the aforementioned pant.
Really solid recommendation overall. Worth checking out if you want a comfy loungey pant that moves with you and skates well. I wish they made it in a more rugged ripstop weave, because that is basically its only downside I can think of.
Carhartt Rugged Flex Relaxed Fit Canvas 5-Pocket Work Pant - These are really solid. Don't move quite as good as the two above pants, but feel very durable as a trade-off. Walk a comfortable line between work pant and casual pant, they sit on your waist rather than above like other Dickies/Carhartt pants. They look nice, and not dorky like a work pant, despite having the durability of a work pant. Move better than the standard 100% cotton Carhartts, and also are slightly lighter weight as a bonus.
I took the advice on here of sizing down the length, and it was a great call. It seems like their pants are all sized to fit over work boots, so keep that in mind. I saw a lot of complaints online about this specific pant (5-pocket flex) being tighter than other Carhartt fits/materials, and that also seems true. I sized up the waist and it fits great.
I like the fit on these more than the Levi's Athletic Taper. I also wouldn't consider these loose fit, but a nice relaxed middleground that feels a bit straight fit in the lower part.
Solid recommendation on these if you want a medium fit, durable pant, that moves alright enough. I'm a bit confused why people choose to skate in the standard 100% cotton ones rather than these or similarly "rugged flex" pants.
Carhartt Loose Fit Canvas Utility Work Pant - A looser lighter fit. They don't flex because they don't need to with their fit and lightweight material. Lighter than the above pants.
However, can be slightly restrictive when lifting knee high though, and I don't think sizing would fix it. This is the best pant I've tried in terms of adding some durability to a lightweight pant. WKND Loosies are lighter weight and move better than these, but these feel more durable as a trade-off.
Definitely size down the length like the above Carhartt pants. However, you can go true size on the waist. I don't think you will really need any extra bagginess. Truly a loose fit pant, but the openings dangling around your ankle aren't a big deal because of how light weight the material is.
Solid recommendation on these if you want something light, loose, but durable.
Let me know if you have any questions.