We've covered what shoes to wear and not to wear with pretty much everything under the sun, including skinny jeans (naturally). And even though my head is always filled with what shoes pair best with what, I was still surprised when I recently realized that I'd subconsciously stopped wearing a certain style with skinny jeans, as it's a big one.
There were a good 12 or so years in my life when the only type of jeans I wore were skinny jeans. But as I got more and more into fashion and eventually started working in it, I branched out. That said, I still wear skinny jeans on occasion but, unlike my skinny-jean-obsessed years, never with heels. Not even low heels or block heels.
It's 100% a personal preference, but there's something about tight jeans that just looks dated to me when combined with heels. (But I will say that 100% cotton, high-waisted skinny jeans are more forgiving.) On the flip side, several different styles of flats are a no-brainer for me when wearing skinny jeans. Shop each type of flat shoes I swear by when wearing skinny jeans below.