The Trend: Over-the-Knee Boots

There's a fine line between street style and streetwalker, and this look definitely straddles the two.

Fashion followers know that lots of designers -- Marc Jacobs, Prada and Louis Vuitton among them – sent models stomping down fall runways in really tall, really sexy boots.

And, now, with celebs from Halle Berry and Victoria Beckham to Maria Sharapova and pretty much every model out there wearing them regularly, this high style is the season's must-have.

But can regular women pull off the look without looking like Julia Roberts in "Pretty Woman?"

What I Wore: There are a variety of tall boot options – flat or studded stiletto heels, plain or covered in fringe, rhinestones or buckles, the list is endless. Black is the most popular color, but grey, beige, brown, purple and (yikes!) red are also available.

I started with Chinese Laundry's "Turbo" in black leather ($79.95 at DSW). With a one-inch wedge heel and an elastic panel; they fit fuller calves and can be cuffed for a below-the-knee look, too.

I then graduated to Via Spiga's gorgeous "Leona" stretch suede boots ($498 at viaspiga.com). With a half-inch platform and three-and-a-quarter-inch heel, they ooze sex appeal.

Where I Wore Them: I wore the Chinese Laundry pair to drop my kid off at pre-K, to the mall, to grocery shop and to a Western-themed charity dinner.

As for the Via Spiga pair, I wore them to -- you're gonna love this -- a Hottest Cougar contest! (No, I wasn't there to enter. I was supporting a friend. Really! You can't make this stuff up.)

The Reaction: I paired the flatter boots with jeans and a baggy sweater. "They're a little wild, but they're fun, right?" I asked my husband, gauging his reaction.

"They're OK," he said, not impressed.

"Well, look," I went on, trying to justify the purchase. "You can also fold the top down. See... they're versatile!"

"Now you look like a pirate!," he declared, proceeding to follow me through the house growling "ARRGHH!" until I threatened to kick him with my new boots.

But out and about, running errands in the chilly weather, they almost seemed practical.

When I pulled on the Via Spiga pair, hubby's reaction was completely different. "Those. Are. Hot.," he proclaimed. He was right. They are hot. Trying to temper the hotness, I paired them with a loose mini dress. Too much. I tossed on a tunic and boyfriend blazer. Closer, but still not right. I finally settled on a fairly prim floral Anna Sui dress. Hot, but not hooker.

"They're not too streetwalker?" I asked my friend at the Cougar event. "You're sure I don't look like Julia Roberts, the prostitute?"

"Not at all!" she replied. "I looove them. They're simple. They're classy."

What the Experts Say: "Here's the thing," says "What Not to Wear's" Stacy London about wearing the tricky trend, "you really can't [wear it] if you're under 5-foot-4. If you're super skinny, sure. Wear them with a mini dress." Just be careful, she warns: "I mean, that's gotta be the most unflattering place for a boot to hit."

But if you do have longer legs, London says, try them with a skinny jean or a longer dress. Of the latter, she describes the boots acting like a legging or "boot tight." (Would that be a "Bight?")

"But, if you're gonna do that, you can't wear something skin tight," London explains. "It's gotta be one of these more loosey-goosey Bohemian-style dresses."

DSW director of merchandising, Valara Gee, says the over-the-knee style works two ways.

"It can be a very sexy look if that boot is on a heel, black leather, top folded with little gold studs all over the cuff," she says.

"And then I think there's a boot that's a little more casual, a little more tough, that has more of a riding boot feel to it. It's flat, with distressed leather, and a great item to wear with tights or tucked-in jeans."

What to Wear Them With: If you have a bangin' body and self confidence to spare, try leggings and a tunic. But, please, nothing tight on top. Your boots are the statement.

Shy? Opt for a slouchier style you can tuck jeans into, or wear a longer dress, so your boots, as London described, almost look like leggings.

The Verdict: This isn't for everyone. But if you're a slave to fashion, and aren't afraid to work it, you can rock this trend, just keep the rest of your ensemble simple.

Leave the "Pretty Woman" moment in your DVD collection where it belongs.

Lesley Kennedy lives in Denver, CO, where she is the editor of Denveralamode.com, a site devoted to Mile High fashion, beauty and trends.