A. When worn in the right way, over-the-knee boots are fab! However, something this cool can turn very bad, like the dumpy hooker look, if you make the wrong fashion choice. Simply stated, keep the stiletto over-the-knee boots for your personal frisky business or the next time you take on a side gig as a back-up dancer on the Vegas Strip.

On a less than provocative note, there is a tendency to get a stumpy, dumpy look as if you are standing in a hole if you break your body up into too many visual breaks. What you want to do is to create a long a lean silhouette with the over-the-knee boots acting as beam to stand you taller rather than cut your down.

The way to chicify over-the-knee boots and give them some edge is too wear them in a way that extends the length of your leg without any visual breaks. Match your tights to the boots or tuck in skinny pants that compliment the color to guarantee a built in leggier feel.  Keep to a modern casual aesthetic with flats, stacked heels, wedges, or any other type of heel that has more substance than a very thin high stiletto to avoid the tacky feel. You can mimic the feel of over-the-knee boots by wearing chunking, knee-topping socks with regular boots and layer over dark tights.

Continue to maintain a longer and lean silhouette by wearing tunic or longer boyfriend jackets that covers your tush and spotlights your legs to create length. Once you cinch in your waist or wear a fluffy skirt, your figure is instantly dissected and the higher boot will further break the line.  Keep your clothing and tights tonal and create interest by adding texture, like suede or chunky knit, rather than with contrasting color.

--December 18, 2008