Ah, fall. Season of sweaters and boots, except that the temperatures are often in flux, and it isn't always cold enough for full-on layers. One way to combat the strange temperatures are balancing out your favorite summer cutoff shorts with layers elsewhere. If you aren't ready to pack your cutoffs up until next May, or just want to give them some extra milage, follow my tips for transitioning your cutoffs for the fall!
Cover up with a turtleneck sweater and add (short) boots.
The easiest way to wear your jean shorts this fall is by balancing out the bare legs with a turtleneck sweater. Pick a comfy knit that isn't your hottest cashmere (because if it's cashmere weather, it's definitely not shorts weather) and hits just at the waistband of your shorts. Add boots, but nothing above-mid calf; the cutoff, thigh-high boot combo can too easily look trashy.
Go casual-cool with a tucked-in tee and leather moto jacket.
If you want to keep the look casual, tuck a loose tee into your cutoffs and add a leather belt, to go with the leather moto jacket you throw on top. Black and white sneakers finish off the cool and laid-back look.
Dress up your shorts with a button-down blouse and blazer.
To make your cutoffs a bit more fall-appropriate (before it's too cold for shorts), dress them up with a starchy button-down blouse, and layer a blazer over. For a casual version of this style, go full-on Canadian tuxedo with a chambray shirt, but either way, tuck your blouse into the shorts and add a belt. For cooler weather, swap out your sandals for booties.
And finally, when it gets too cold for bare legs, add tights.
To avoid looking like you just slapped a pair of tights on under an otherwise summery outfit, pair your cutoffs with a darker-colored shirt or sweater, and wear booties under your tights. Pair your shorts with a top that's high-necked if you're wearing tights, to keep the proportions somewhat even from top to bottom.