Can someone please explain boots to me?

The first snowfall happened the other day, and so the kerfuffle in my brain started up again, as it does every year at this time:
Do I need boots?

I've never been on Team Boot. I've always been on Team Shoe. Even when I was a young MC, I would sneak out of the house in the morning before my mom could rein me back in to put on my boots. I'd leave them at school, kick one off on the way home, put them on my snowmen -- anything to not have to wear them. Finally, in about the fourth grade, my mother gave up and stopped buying me boots. Until last winter I was boot free. Sure, my shoes would get salt stains and I'd have to get them reheeled weekly, but still I just felt like I'd rather have pretty footwear than sensible footwear. I've really never understood the whole changing-shoes-at-work ordeal. After all, the people at work know you and every outfit and every pair of shoes. They see you everyday. Isn't it the people on the street - the friends and colleagues you bump into randomly once every few months - that you'd rather see in your pretty heels than in sneakers, flip flops or fuzzy boots? Maybe it's just me, but also, I don't want to carry an extra bag with my indoor shoes as I walk to work. Also, what do you do if you have to go out after work to an event or to meet friends? Are you supposed to wear your big boots? What if you're having cocktails? Do you change back into your shoes at the bar? Does the bartender stash your boots? Or do you wear your shoes and then carry your boots? But what if the bag you carried your shoes to work in isn't big enough for boots? It just seems so confusing.

Anyway, last winter, something snapped. Maybe it was one too many winters of slipping along the streets and getting salt stains on the bottoms of my pants. I don't know but I decided perhaps it was time to try out for the other team. Give boots a chance and all that.

So I went with the big furry boot trend and bought a brown pair that matched my coat. They were so comfy and warm and cute - I really did love them, but only with skirts. With pants, I just looked like some sort of abominable snowman. I would tuck my pants into them but they'd billow out at the tops. It was completely ridiculous and I'd find myself taking back streets to and from work just to avoid running into anyone I knew.

So those boots are not going to work again this year. I need a new plan. I just don't know what it should be. I don't understand boots. I mean, most of them work when you're wearing skirts, but what are you supposed to do when you're wearing pants? If you get the skinny boots, how do you tuck your pants into them? Or are you only supposed to wear skinny pants with them? Or are you supposed to leave your pants outside the boots? If I'm going to get boots I'd rather just get flats that are super warm and comfy but then I'd have to tuck my pants in because all my pants are hemmed for heels so if I left them out they'd drag on the ground but is it totally weird to tuck them in? And what if they can't tuck in because the boots are too tight? I just don't get it. And if you get the pretty boots with the heel then isn't it just like trying to wear stilettos in the snow - so then what's the point of getting boots?

I don't think it should be this difficult. Is it just me that finds this all incredibly complicated?

At this point the only solution I can think of is to buy a pretty yet flat and comfy pair of boots and only wear them with skirts. So, save skirt days for snow days and wear pants and shoes when the sidewalks are clear. Does this make sense?

As I'm writing this, my friend just emailed me. She'd asked if I enjoyed the first snowfall last Thursday and I told her I'd had to take a cab to work because I was sliding on the sidewalk in my stilettos and I can't figure out what to do about boots. Then she said that was totally understandable and that just because it's snowy doesn't mean you have to resort to frumpy footwear! See? How am I supposed to overcome this dilemma when I've got friends reconfirming the way I originally felt? Is it really okay to just take cabs when it snows? Is this really a solution for winter?

Help! What do you do?

Signed,

Bootless and befuzzled.