Or maybe I should have asked ‘How to look like off-duty models in the cold season?’ Cause it seems to me these girls have their well picked uniforms and fabulous effortless styles for all seasons, and in autumn and winter they’re all seen in their cut-off denims or leather shorts with chunky sweaters, leather jackets or coats, and biker or over-the-knee boots. And sometimes, when it’s freezing they’ll sport black sheer or opaque tights. Amazing, if you ask me. 
The SHORTS-in-the-cold-season look has definitely translated into a trend for the past couple of years, courtesy of these models and us as well. Whaaaat? Well… I happen to think we’re also baring a tiny bit of blame for the shorts in winter style, just because we can’t yet part ways with these items once summer’s gone.
So… as any brilliant minded sartorial defying blizzard would do, we too came up with this trend. As long as the feet are comfortable (or not) and warm in boots and thick soft socks (over-the-knee styles look amazing), and we’re all bundled up in layers of knits and shirts and tees and wrap coats (this season’s massive trend!) a few inches of leg skin is ‘whatever’ you know.
Not to mention that if you’re too cold, or love the grungy cool style, you can definitely resort to those sheer or opaque black tights. Or even pattern styles. 
What’s the secret to nailing the-shorts-in-winter look? Nothing much I think, because they’ll instantly look fantastic paired with autumn and winter items: sweaters, shirts, vests, jackets, coats and what not. In terms of shoes, which set the tone for the whole look, anything goes from ballet flats, to biker boots, to sky high heels, to sneakers.
Do all summer shorts work in the cold season? I kinda think they do, so YES from my part. I’ve worn light colored and different fabric shorts in freezing temperatures paired with chunky sweaters and black tights and I like to think they looked OK. Truth is I’ve always loved the clashing of season fabrics and thought a pair or lace or silky shorts look fantastic with a cable knit sweater and high boots. It looks sophisticated.
So YES to all shorts in winter if you ask me. Except maybe for white ones. Although even those can work paired with a black sweater, black high boots and bare leg skin. Or maybe except for those beach-shorts. Yeah, I’m guessing those are a no-no. 
Easiest shorts styles to don in winter? By far the high waisted ones! I love those loose cotton & leather styles, jacquard, sequins, also look so luxurious, plaid could even work if you love it, and last but not least denim. A pair of denim cutoffs will ALWAYS look effortless, cool, grungy, edgy, or chic, depending on your personal style.
Where to wear shorts in winter? Well… this might be the tricky part. Short shorts are a no-no for the office, even with tights, buuuuut those loose high wasited styles that resemble skirts – those – I think can look quite chic and professional paired with a blouse & blazer & ankle boots or ballet pumps.
Also perfect for the office are the knee-length shorts especially when paired with a color coordinated blazer. Think short business suit. For autumn days.
The rest of your summer shorts can basically go anywhere in winter, except the beach you know. And for some fashion inspiration, let the photos roll… 
Do you wear shorts in the cold season?