Jeans, sweater, booties, repeat. If you don't push yourself beyond this tried-and-true combination, fall dressing can get old...fast.

Don't get us wrong — there have been many a chilly autumn morning when that's the exact outfit we reached for. But, if you really want to wear your ankle boots all season long without getting sick of them, you'll have to get a little more creative with your ensembles. Fortunately, a versatile bootie can finish off a variety of different looks, whether you play with proportions and pair them with a contrasting midi-skirt, or you match them with long, loose silhouettes.

To give this go-to shoe the attention it deserves, we're showing you five fresh ways to wear the pairs you already own (with a few shopping suggestions in case you're looking to score a new option, or two). Booties were made for walking (yup, we went there), so stride right into one of the solid outfits, ahead.