No peep toes for me!
I'd say about 80% of the time, my winter formula is:
- cami - I like synthetic instead of cotton in the winter, because it's warmer
- blouse or knit top
- long sleeve merino wool cardigan - I like merino because it's warm but not bulky
- skinny jeans tucked into boots, or bootcuts with booties
- cashmere wool socks
- 3/4 length wool coat, or puffer coat if it's super cold
- scarf, gloves, hat
If I have reason to wear dress slacks, I will wear lined wool slacks. If I'm driving in the car for awhile (like into the office) then I'd opt for a shorter coat (car length).
If there's lots of snow on the ground, I wear Uggs, because they are practical, and switch into nicer footwear once I get where I'm going.
As for skirts and dresses, I do wear them on occasion in the winter, but I have to say, it's not my preference because I get cold too easily - even with a full length camisole, tights, boots, and socks under the boots. It's having the cold air on my knees and flying up my dress... brrrr. So I'm much more apt to wear skirts and dresses in the summer. Once it hits the freezing mark and it's snowing, it's much harder to entice myself into a dress.
But, I don't think skirts with boots are hooker-ish at all! I suspect your eye just needs to adjust. You might try wearing a flat boot with skirts first. Boots with skirts are just so practical.