For most of us, "thigh high" is not the most inviting fashion phrase ever uttered.

But after laying eyes on Stuart Weitzman's gorgeous "HiLo" boots, $650; Jildor.com, you might be singing a different tune, which is why we're offering you a chance to win a pair!

There's no denying that this uber-tall style is the boot of the season and, surprise, Victoria Beckham led the way.

If you thought you'd never go this far, a top designer's words of wisdom just might change your mind about how to approach this huge trend. Think: Parisian woman fetching coffee and croissants in 1968, not pre-makeoever Julia Roberts in "Pretty Woman."

Shoe guru Stuart Weitzman gives StyleList tips for pulling off (er, on) the trend.

• These boots are made for a woman who wants to be noticed. Comfort and confidence are key.
• Stick with classic colors. Brown and black work, and the less ornamentation the better.
• It is OK to show skin with the high-heel thigh high. But with the flat thigh high, it should be worn with tights, with jeans tucked inside, or with a mini skirt paired with tights.
• I would say these work best with a simple outfit. Color is certainly not forbidden, but let the thigh-high be the wow factor and the ultimate accessory.

Check out other chic over-the-knee styles at Jildor.

And now that you're a convert, enter to win your very own pair of this season's must-have item -- the Stuart Weitzeman "HiLo" boot.

Here's how to enter:

• To enter, leave a confirmed comment telling us what you'd wear the boots with.
• The comment must be left before 5pm ET December 15, 2009.
• You may enter only once. One winner will be selected in a random drawing.
• One winner will receive a pair of "HiLo" Stuart Weitzman thigh high boots (valued at $650).
• Open to legal residents of the 50 United States, the District of Columbia and Canada (excluding Quebec) who are 18 and older.
• Click here for complete official rules.