Non book related rant ahead....
Earrings: No matter if you're wearing studs or big old chandeliers the same thing always happens. They get stuck in your scarf. I've almost ripped my earrings out enough times that when I take my scarf off it's like sloooooowly unwrapping a bow.
Headwear: I have given up on trying to find a hat that is cute AND professionalish AND warm. I have several hats and none of them cover all of the bases. If it's seriously cold, I don't care if it's cute or professional looking so I wear my hat that looks something like this:
(Though weirdly enough I get compliments on it all the time. Which, I don't understand but I will take). And then no matter headwear you wear your hair is either smooshed to oblivion or as staticky as all get out. Or if you are a lady with particularly voluminous hair and you can't find a hat that will cover all of your hair and stay on your head then you have to do the wrap around ear muffs and those just aren't as warm.
Makeup: When the wind really get's blowing and it's freezing and it makes your eyes water and your mascara streaks and everything thinks you were crying. Or when your make up rubs off on your coat collar and scarf and hat because you are trying to bundle everything in to cover your face.
Coordination: Most people don't care, but I have been conditioned to never simultaneously wear anything black and brown at the same time (khaki is fine). And so I have a pile of brown hands and gloves and scarves and a pile of black ones, so I don't mix.
How I cope: I stop caring how my makeup looks and if my hat and gloves coordinate. I do care about ripping out my earrings because ooooooooooooouch. I know that everyone else is dealing with mostly the same issues so I shrug my shoulders and say "Meh, all of us are cold and yet kinda sweaty and have frozen boogers. So what can you do?"
One perk: You can get away with wearing a bra a little less. Little miracles.