Can i wear jean skirt, tights/leggings and black converse hi tops? or skinny jeans with the hi tops? or both?

i mean 4 the colder days like later wen fall comes or shud i jus screw this whole converse thing and stick with sneakers? because im reli startin to like converses and wanna get one but need to get other stuff to match it. i like the hi tops better tho than the low ones.