If it's so cold that you actually need boots, I would tuck some skinnies in. Jeans are trending very tignt and sleek, the opposite of what boots are. Good boots in fine leather might go well with longer skirts and winter dresses. I like to wear a long gored black wool skirt with boots when it's too cold to wear anything else. This has a pioneer woman look. The skirt has a certain swirl to it.

Western boots are usually worn with jeans in Texas. These would be 'boot cut' jeans, but this is a regional style. If you are in Texas and have fabulous legs, you might even get away with western boots and a short, swingy skirt at a dance hall in the evening. 

Short boots or booties, are really just covered up shoes and not boots at all. They seem to go with everything. 

The skinny jean is a heavier weight than a jegging (legging made out of a lightweight stretchy denim), has all the trimmings of a typical jean (pockets, zippers, belt loops, etc.), but has a very narrow fit. What was originally found to be a cut only models could carry off, skinny jeans are now a commonplace silhouette worn beautifully by women of all shapes and sizes.

The skinny jean is perfect for tall boots, be they over-the-knee heeled boots, flat riding boots, cowboy boots, calf-height harness boots, or a slouchy suede wedge. The skinny jean hugs the leg making it less likely to bag at the knee or wiggle its way out of the boot shaft. The slim silhouette makes the bulk of a boot look more elegant, and works with the chunky and slouchy knits this season.

The skinny jean is also perfect for ankle booties. Be they short harness boots, lace-up combat boots, or ankle-high cowboy boots, a skinny jean tucks into the boot nicely and shows the shape of your calf above the boot’s opening. If you find your jean likes to wiggle out of booties, consider tucking the hem into a pair of socks; they also sell suspenders specifically for this purpose!