Most-Googled: How Do I Wear Ankle Boots?

The Web puts answers to every conundrum at your fingertips, but do you really want to seek fashion and beauty counsel from whoever turns up at the top of the page? In a pioneering collaboration with Google, we quizzed the non-virtual pros for answers on the Internet’s most-searched style stumpers.

So you're stuck on what to pair with one of the season's hottest shoe silhouettes? Well, we're thanking the shoe gods for shorties this fall—they're flattering, versatile, and unlike midcalf styles, they're good to go all year long. Pair low-slung booties with skinny jeans or a short, floaty dress to help make you look a little more statuesque. To achieve maximum leg length, keep everything below your waist in the same dark color family with skinnies or dark tights.

If you're rocking a more casual ankle boot (think flat or low-heeled) opt for a style that hits just below the ankle bone, advises celebrity stylist Joseph Cassell (known for getting together Taylor Swift ready for the red carpet). "But when you wear a heeled bootie, I think it’s cool when it rises above the ankle slightly because it gives it a dressier feel," he adds.

Feeling daring? Don't put away your summer shorts just yet. "One of my favorite things that I’ve seen for fall is when women pair shorts with thick tights and an ankle boot," Cassell says. "I think it’s adorable."

For expert answers to more commonly googled questions, head toinstyle.com/mostgoogled.