Even though shorts are often considered to be ideal for summer and spring, they can also be a flattering option for the cooler months, like Winter season. Just remember that you may need to dress them up with a stylish blazer, warm tights that will add a chic appeal. However, if you do decide to rock a pair of shorts in January or February, it’s important to keep your outfit in shape by stocking up on layers such as turtlenecks and cardigans.