While out and about yesterday, I spotted a girl looking absolutely adorbale in shorts, paired with tights, boots and a long jacket. The shorts just gave the whole outfit that extra edge, even though the rest of what she was wearing was rather plain. That's kind of what you need though to balance everything out to pull this look off for everyday wear, since shorts in chilly weather would otherwise stick out like earmuffs on a 90-degree day. I put together a couple nighttime looks featuring shorts. I'd wear both outfits with black tights. and keep accessories simple since the shorts on their own make a statement..

Sweater: Soft and sexy wrap; victoriassecret.com
Shorts: Jewel button shorts; forever21.com
Necklace: UO tassle lariat; urbanoutfitters.com
Boots: Chinese Laundry Kingdom; piperlime.com

Sweater: Cascade cardigan; anntaylor.com
Shorts: Sequin glam short; forever21.com
Blouse: Kimchi Blue beaded tier tank; urbanoutfitters.com
Bracelet: Heidi Daus "Irresistibly Yours' bracelet; hsn.com
Booties: Vince Camuto Missie boot; endless.com