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I love wearing my Doc Marten boots with dresses to girly them up a bit because I will admit, I did feel sorta butch for wearing them at first. Especially when I got awkward stares from people who didnt understand the classic of Doc Martens and assumed I was wearing some kind of goth combat boot. Hah.
But I do think people with smaller feet look better with Docs. My friend had once tried on the yellow patent ones and she felt as if she were wearing school buses on her feet. Im a size six and they look okay, but mine are also plain black. If you have bigger feet, try not to opt for a bright color.
And like everyone else says: skinny jeans, or like me, I do it with tights. Nothing bulky on your legs. Thats too butch. Let the Docs be the only bulk on your legs. And I dont think it should matter whether you have skinny or chubby legs. They should look AWESOME either way!