The Most Flattering Skirt Length For Anyone, Any Age (VIDEO)

03/25/2015 09:17 am ET | Updated Mar 25, 2015

As they age, many women start to rethink the fashions and styles that have carried them into adulthood. Suddenly, they find themselves wondering, is this top too low-cut? Can I still pull off that statement necklace? Do those shoes look too "young"? Or, in the case of 48-year-old Leslie, is my skirt too short?

As a single mom, Leslie is in the midst of this fashion dilemma. She still wants to look sexy, but she doesn't want to look like she borrowed an outfit from her 21-year-old daughter. To help her figure out how to toe the line, Leslie gets help from O, The Oprah Magazine's Creative Director Adam Glassman, who invites her inside the magazine's fashion closet for a candid style makeover.

When Leslie arrives, she's wearing a thigh-length miniskirt, a simple black top and a jean jacket. Glassman does a double-take. "Where the hell are you going in this outfit?" he ribs.

The miniskirt, he declares, is not age-appropriate. "You really are genetically blessed and you have fantastic legs," Glassman begins. "But I don't actually believe you should always show them off at all times, in this way. You're dressing too young for your age."

Instead of a miniskirt, Glassman offers another alternative.

"I'm a big proponent of the pencil skirt," he says. "I think, no matter what your age is, a pencil skirt is the most flattering skirt out there."

Leslie eyes the knee-length outfit and isn't completely sold. "Now, bear in mind, I am single," she tells Glassman.

The pencil skirt, he responds, is still sexy -- just a different kind of sexy. "It is possible to look sexy, hot, youthful without looking like you're trying too hard," Glassman explains. "Too short makes you look like you're trying way too hard. Not a good look, especially for attracting... the kind of man that [you want] to attract."

He sends Leslie away to try on a fitted sheath dress with a conservative v-neck.

leslie skirt length adam glassman style

"Fantastic!" Glassman says. "Do you feel, still, your age?"

"I do... and I feel a lot more comfortable," Leslie says, smiling. "I actually feel more confident!"

"So, our lesson today: Shorter doesn't always mean sexier," Glassman sums up. "You look hot."

Another fashion to retire along with that miniskirt: Jeggings and leggings -- Glassman insists that they are not pants.

What's your fashion question for Adam Glassman? Tweet him using the hashtag #AdamSays.

Also on HuffPost:

Miniskirts In The '60s
Suggest a correction