(mine. classic 14-hole, mid-calf height)
So what makes Docs so great? First of all, they're boots, which automatically makes them superior on my shoes hierarchy. I almost always wear strictly boots for 3 seasons out of the year or else my ankles feel naked and cold. But more than that... they look good with absolutely anything you wear. They're timeless.
The first time my Dad saw me wearing my boots, he called me a Neo Nazi. Um, not exactly. I think there might be some kind of combat-y stigma associated with docs still, but that connotation is gradually going away. They come in so many colors and patterns now that anyone can do what they want with them. Let's see some of the many faces of Dr. Martens...
First of all, docs are a punk staple. It's a very British thing. Dr. Marten even hires punks to stand around and do their advertising. Personally, I think punk fashion is so bomb. I've said this before, but anything that stands out and is borderline obnoxious is A+ fashion to me. Peep this tumblr for more, it's my favorite: lycanthropunk.
Who says docs are only for the hardcore and heavy duty? Here we've got a collared shirt, sweater, and a blazer. Quite different from punk, no?
Loooolita inspired! I love loli, it's so bold although it lacks the intention of being bold. They're not usually going for shock factor, like most punks, but they end up getting the same kind of reactions. White docs are amazing but I think I would probably scuff them up horribly the second I step outside.
There's something proportionately off about docs that I like. I have long legs and big feet, making them kind of like clown shoes since the actual foot part is so large. I like them that way, they stand out.
Now this looks relatively "normal" by modern standards, right?
Experiment. Stand out. Make people question your fashion sanity. And wear docs. You can be whatever you want.