Denim shorts are a great casual outfit pick for the spring and summer, but you can also wear your favorite pair into the fall. Choose accessories and other pieces that make the outfit warm enough to wear as the temperatures drop. If you do decide to wear your shorts in the fall, go with a higher waisted, wider legged pair rather than a pair with a low rise and skinny fit.
Bring your shorts into the fall by adding a pair of knit tights and a pair of ankle boots to them. Since jean shorts will look strange if they are tight on your legs and you wear a pair of tights underneath, you need shorts that are wider in the legs. Shorts with an inseam of at least 4 inches work best for wearing into autumn. The shorts shouldn't be too long, either. The perfect length falls to the narrowest part of your mid-thigh.
Choose tights in an opaque color. Fishnets will look a bit too scandalous while sheer nylons will make you look as if you are trying to hide your legs, rather than extending the season of your wardrobe.
Pick a pair of ankle boots with fun details. Look for boots with buckles or buttons on the ankles, for example. A cute pair of oxford inspired booties is a great pick, too. Go with a neutral color, such as dark brown or black. You can play with color with the tights, but you want to get the most wear possible out of the boots.
On top, wear a shirt that's a bit more traditional and weather appropriate. Cable knit sweaters are always in style; pick a thin, not chunky, cable knit sweater in cotton. Don't be afraid to pick a colorful sweater. You can also go for a button up shirt, such as a plaid flannel shirt or a striped oxford. Another option is to wear a sleek, long-sleeved T-shirt with a fitted, button-up vest. The vest will nip in your waist ever so slightly.
For a tough look, add a cropped leather jacket such as a motorcycle jacket to the outfit. For a bold look, choose a leather in a bright color such as Kelly green or hot pink. Keep in mind that leather jackets are usually pricey and considered investment pieces, so only go with the bright color if it is a shade you know you'll wear for years.
Another option is to pull a military-inspired, cropped jacket over your shirt. Go for a jacket in an olive green or khaki color. Make your outfit work appropriate by pairing a dark pair of denim shorts with a cropped, black blazer.
Accessories can also help you bring a pair of denim shorts into the fall. Wrap a printed, cotton scarf around your neck. Choose a scarf in deep colors, such as navy blue and burgundy. Add a touch of coolness to the outfit by topping it off with a wool fedora. Set the fedora at a jaunty angle on your head and you'll be all set!