This was one of my favourite looks on the streets of NYC last week. Young gals pairing short shorts and bare legs with all sorts of boots. The boot silhouettes ranged from flat, casual and rugged, to high heeled and dressy. From ankle length booties to mid-calf and knee-high lengths. Cheeky, edgy, youthful and fun. I can see the look transition into cooler weather with fun hose and tights.

I prefer the shape of short shorts when they are on the baggy side. Somehow, that looks more modest to my eye. As does the fact that they are “short trousers” and not a short skirt. If you’re going to wear a hemline this short – trousers offer more coverage than a skirt.

If you have youth on your side and are comfortable showing lots of leg, please try this look so that I can live vicariously through you! If I was 10 years younger, I’d be all over the vibe. I’d wear baggy short shorts, unstructured blouse or shirt, cropped jacket or blazer, and killer boots.  What do you think, ladies? Do you like the combination? Would you sport it now? Would you have sported back in the day?