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How NOT to look Slutty in Thigh-High Boots

December 18, 2010

When people think “over-the-knee boots”, sometimes, this image pops into their heads:

That’s right, it’s your favorite Hollywood Movie Hooker, Julie Roberts, in her break-out role Pretty Woman. How can we forget her loveable hooker persona? She gave prostitutes a rather good rep; her bubbly, sassy, vulnerable character almost made me want to be one too..if that meant winning Richard Gere.

I was about seven years old when I first watched the film and I was completely mesmerized by the Vivian character. Of course I didn’t exactly know what a hooker was at the time and I didn’t understand the real story behind the plot, but I loved the makeover scenes; how Vivian transformed from a cheap and trashy call girl to a classy and sophisticated dame.

It seemed that as soon as she took off her black latex stiletto heel boots, her slut-factor went down by 50 points. It’s rather amazing really how shoes can change the entire look of an outfit. Not only that, but they can also change some one’s persona. Shoes have transformative power.

So when it comes to the case of the over-the-knee boot, one has to be extremely cautious not to fall into the “whore” category when wearing them. It’s all about making appropriate choices for your top and bottom to avoid looking like a bad girl (unless of course you want to). Here are my DOs for wearing those thigh-highs.

1. Keep them Flat

Flat over-the-knee boots are definitely much easier to pull off (literally too) than high-heeled ones. Pair them with skinny jeans and a simple sweater and you’ve got a winter, cozy-chic look. Try them with thick wool leggings and a cape (my favorite trend this season). Here are my picks:

Cervina Over the Knee Shearling Boots by Hunter in cream, $374.50 (orig $535) from

Sam Edelman - Pierce Over the Knee Boot in Whiskey Leather by Sam Edelman, $240 (org.$300) at

Air Marisol Over the Knee Boots in Brown Suede by Cole Haan, $295.80 (Reg. $348.00) from Macy's

Inspiring Over-the-knee Boot by Audrey Brooke, $149.95 (Reg. $189 ), from DSW













2. Keep them Leather or Suede

The quality of the boot really makes a big difference too. It’s easy to see when leather is fake and when it’s the real stuff. And unlike real fur (which you all know I think should be banned from the fashion industry), real leather is visible miles away. It’s a no-brainer that wearing something cheap will make you look cheap too.

Matiko Cadie Over the Knee Boot, $249.95 (Reg $330) from DSW

DV by Dolce Vita Women's Kiki Over-the-Knee Boot, $179.95 (Reg. 191.25) at

Sam Edelman Sutton Suede Boot in After Dark Suede, $159.96 (Reg. 199.95) from












3. Avoid Short Skirts

Nothing says, “f*** me now” than wearing high-heeled thigh-highs with a mini skirt. Unless you’re going for the Pretty Woman, pre-makeover look, I would strongly advice you to avoid this look at all costs.

4. Make sure you got the legs for them.

We aren’t all born with supermodel looks. That’s a sad, sad fact of life. With that said, we don’t all have long-ass, thin legs like Giselle. So just because you see a model in Vogue looking fly in boots that showcase her long stems, doesn’t mean that you will. Ya, that sounds harsh, but so is fashion. In most cases if you’re under 5’5″ knee-highs will just look plain silly. So, pick a different boot, like a wedged bootie, which would be much more flattering.

5. Act like a lady.

No matter what you wear, the most important element of your outfit is your personality. How you behave, how you compose yourself, and how you interact with others really can speak louder than your dress (or in this case boots). Obviously if you’re crawling over every guy at the bar and flashing the club owner while pounding down 10 lemon drops, every thing about you will say slut. So, do yourself a favor and act appropriately; when in doubt, think of what Grace Kelley would do; that way you’ll avoid giving yourself a bad rep. Then it won’t matter what you’re wearing (to some extent of course); all any one will really notice is your undeniable charm..I mean even hookers can have charm.

Here is the thigh-high boot look done RIGHT:

obviously Rachel Zoe knows how to do it right

Street Chic

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