I am absolutely the wrong person to ask how to get out of a clothing rut. I've been in one since I had to stop wearing a uniform every day.

First and foremost: I love that tweed jacket. It is an absolute rip snorter. I would love to have something as nice as that little baby and you could bet that I would wear the heck out of it if I did.
Your jumpers are super cute too. And you know know I feel about that chunky sock business. Top shelf cuteness.
But I guess your lament is not about whether or not you have cute winter things that can make cute winter ensembles. It's about the fact that being cute ceases to be a primary motivator for what you wear when it's really cold. And that's sad. While I know all of this to be true, being in NYC is cushioning me from the reality of this situation. Up until a few days ago, the weather has been so very lovely.

It was sunny when we went to the Empire State.

It was sunny when we caught the ferry to Ellis Island.

It was sunny when I walked through central park coveting dogs, especially this Boston terrier who I dreamed of taking home with me and calling him Wallace and living very happily together.

I know I'm living in a fools paradise though. That dog's probably already got a perfectly good name and calling him Wallace will not help his transition. JOKIES. I mean of course I know that I am coming home to winter and should be preparing for it by buying sensible winter clothes. Its just so hard to find them in a city that is going bananas for summer, and when I do find them, they are super expensive or just look kind of lame on me. Which, as you know, is the story of my life since I left school and the sweet refuge of wearing a uniform every day.
But I did find this awesome thing that I love and would be super practical for winter.

But was $450. And a cape.
Anyway, at least you've got that super awesome coat you bought in NYC. That's got to help.
And maybe you're just going through a necessary period of transition that will soon be over and soon make way for all the fun of compiling super cute wintry looks? That's possible, right?