I’ve decided I’m okay with the whole shorts-over-leggings-in-the-winter look. On 3 conditions:
1. The shorts can either be short-shorts or boy-shorts (to the knees) BUT they have to made of some kind of winter-appropriate fabric, i.e. twill, knit, tweed. NOT cotton or spandex or jeans. Same goes for the leggings. Knit stockings = good, spandex or nylons = bad.
2. The shoes make a big difference. My shoe of choice to top (bottom?) off the outfit? Tall-as-possible leather boots. Over the knee? Hell yeah. Heel? Take it or leave it.
3. Colour. Please, stick to the tried-and-true winter colours. Natural twills and tweeds, and grey, brown, black leggings. No stripes! I saw a striped short, striped legging combo and I had to turn away.