Even in the summer, shorts as office attire are subject to scrutiny. Heaven forbid that something so tied to leisure be brought into a professional environment. Staunch shorts opponents would go so far as to deem a miniskirt more suitable, despite the fact that women run a far higher risk of exposing their lady gaga.
It's no surprise that winter shorts, which were donned in many a fall fashion show this year, have never achieved the status of the pencil skirt. Not only are they ill advised for many body types, but the very notion is as risible as a summer parka. Even so, they tend to return to runways and retailers every autumn or three as surely as cranberry sauce at Thanksgiving.
Is it possible to get away with wearing shorts at work in the winter? Let's call this a heavily qualified yes. The biggest consideration is fabric; think wool or other heavy materials (and absolutely no khaki, summer prints and pale colours). It's also critical to keep the remainder of the ensemble as classic and business-appropriate as possible. A jacket that falls just below the waistline is ideal, while legs should be covered in opaque hosiery. A calf-high boot or ankle bootie is preferable to a strappy heel or stiletto.