Riding transition with pads, it works great, IMHO. Otherwise, depends on lots of variables already mentioned. Can be turboclown, can be great.
So can every fit, especially when it's clear you are trying to be fashionable when skating....such as people who commonly use
drip.
Like pants too big or too tight. If you have to adjust your pants before a trick, something isn't right; you shouldn't have to worry about it.
Shorts are great, lots of shinners.
Low tops are great, lots of ankle/snake bites.
To each their own tho, I wear skate clothes that are comfy, not restrictive with no fucks given to style because they're going to get wrecked. Off the board is a totally different story.