Ah, layers. I grew up in Wisconsin so I like to think of myself as something of a layering expert. In my early days I used to take it to extremes - in college I would often layer flannel pajamas under wool skirts to keep warm in the winter. I'd like to think my layering habits have matured a bit since then (I really make an effort not to wear my pjs out of the house now), but I still rely heavily on the basic techniques. And one thing that I've learned is to embrace the layer, rather than hide it.
So here I am, with my wool trousers worn over some cashmere and silk blend leggings, draped over the tops of my boots rather than tucked in. I sort of like this backwards sock effect. Sort of Dickensian, no? Not something I usually look for in my styling, but I think it works here, so I'm going to go with it. All winter long.
Do it yourself...
All these pieces are no longer available (read: old) but you can always find similar items, like these: