I have always wanted to try the shorts and tights pairing but never had the guts to do it. Wearing tights with all the shorts I owned at the time just looked goofy. I recently bought a new pair of shorts, and paring them with tights looks so effortless, I absolutely love it. I believe it is because they are a higher rise and wider leg than most shorts, which I think is key. It achieves nearly the same silhouette of short A-line skirt, but with way less risk of having the SF wind blow up your skirt.
(I promise my eyes are open for this shot!)
Shorts & Blouse: Anthropologie. Blazer: Thrifted. Shoes: Schuler & Sons. Scarf: Handmade by me. Belt: Came with Anthro shorts. Tights: H&M. Bag: Schuler & Sons. Octopus Bracelet: Gifted Vintage. Sunglasses: Ray Ban.