Uhm… sans looking like a professional ‘Pretty Woman’ who’s stuck in the 80s in latex and way too fitted mini dresses on an incredibly hot body nonetheless, with a beautiful head the size of a IRL barbie doll – perm curls, pink lipstick, blue eyeshadow et all. Three things the 80s bombshell borderline call-girl always seemed to have on: a lot of sass, a lot of hairspray, and a pair of thigh high boots.

Fast forward a few decades and 2 things continue to reign the trendy sartorial world: sass, which is replaced by swag, so tomato tomato there, AND thigh-high-boots, the latter being still the hottest shoes in history, with the most epic superpower of them all – they can wowza any outfit in a millisecond, dressing up the most boring piece of shit you have on. On one condition: that you dare to wear them.

Aaaah but you see the plot thickens right there. Pulling these suckers on, all the way up to your crotch if you’re a brave fashionista ain’t enough. You gotta take these borderline vulgar, BDSM, way, way, way, way, way too hot (as Drake would say) booties and make them stylish. Daytime stylish. Office stylish. date-night stylish. Dinner stylish. Casual sophisticated stylish.

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How the fuck are we supposed to wear prostitute high heeled boots, all the way up to our vajajay, pair them with a skirt or a dress and  NOT look like a professional booty caller?

Three things my wonderful lot: style, style, style. Did I say style?

Joke aside, here are a few 9 tips to make the hot booties work with skirts and dresses in a very sophisticated, cool, even professional sort of way.

1. Never EVER wear platform thigh high boots.


2. Quality first and foremost.

Pick thigh high boots that look expensive, are comfortable and fit well. It’s a statement piece, a rare fashion investment, so do it wisely.


3. Mix and match textures.

Leather thigh-high-boots look great against thick knits like a massive sweater dress, or an oversized cardigan. Suede thigh high boots look fab with a silky dress.

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4. Peek-a-boo gimmick.

Show just a tiny little amount of skin leg in either a pencil dress or skirt with a slit, or when pairing the THB with a mini dress or mini skirt, make sure their hems meet pretty close. To avoid the Pretty Woman channeling.

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5. For office pair THB with a pencil skirt or dress, either with a tiny slit or not.

The effect has to be that of dress over leather pants or leather tights with heels. No skin in sight. It’s a very fashion editorial meets street couture sophisticated office outfit.

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6. For evening/dinner/fancy-schmancy encounter wear leather THB in black, with a black silk slip on dress, knee-length, high slit, lace hems, bare back, and add a fur coat over.

Plus the inherent bling, which can be over-the-top opulent or just dainty, whatever floats your boat. It’s a dramatic incredibly sexy very tasteful outfit.


7. Casual daytime-to-evening look.

Pair the THB with a sweater dress that’s down to your knees, or a flirty knee-skirt with a tee and cosy cardigan on top. A wrap coat, a cape, or even a fur vest compete this chic but relaxed outfit.

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8. Clash styles & textures.

THB by definition are statement, over-the-top, kinda posh item, so it’s very easy to balance this effect by pairing them with something basic, simple, cozy, like a knee-length jersey dress par example, like a short A-line skirt with a 70s turtleneck, a vintage denim or suede dress… anything that’s not too in your face will work with THB.

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9. Avoid too fitted clothes

And instead opt for layers, oversized, or play with fitted versus oversized pieces.

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Image by Micah Gianneli & Jesse Maricic| http://micahgianneli.com

Image by Micah Gianneli & Jesse Maricic| http://micahgianneli.com

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Images by Jesse Maricic & Micah Gianneli | info@controlecreatif.com | www.controlecreatif.com

Images by Jesse Maricic & Micah Gianneli | info@controlecreatif.com | www.controlecreatif.com

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As much as I bitch around here with THB being borderline BDSM or too vulgar, I’m on the YES side of these little suckers, and would wear them from morning to evening, with skirts, dresses, shorts, jeans, and what not. From over the knee high to crotch high, I would not take a step back from walking in these shoes. What’s stopping me, you might wonder? Not having found a pair that’s long/high enough that’s all, OR, when I did they had the stripper platform (over my dead body), or looked cheap.

I did however spend the morning making all sorts of wishlists and THB are in there, so of course I got my picks for you below. Some of them a bit pricey, but I’m seriously considering splurging on these.


‘Pretty woman walking down the street, pretty woman the kind I’d like to meet.’ Whatever… We don’t do pretty around here. We do bold, we do hot, we do funny, we do smart. Sassy… Cool. We know too many tricks and too many things to be just pretty girls in THB.


4 replies
  1. Grace says:

    It’s exhausting to search out knowledgeable people on this subject, but you sound like you already know what you’re speaking about! Thanks

  2. Cheryl says:

    Awesome post! I absolutely love my new thigh-high boots and have only put together two outfits where I don’t look like a hooker LOL.

    Oh, and I truly love your site. I only recently started following your blog, but I’m thankful for it! I just got out of the military and have been wearing a uniform more than ten years so I have to relearn how to dress well and your blog is helping me out :) I also enjoy your smart, funny writing and the fact that this is not all about haute couture and $10,000 dresses. Keep up the great work!


  3. Ana @Champagnegirlsabouttown says:

    Totally on board with no 5! I love wearing my suede over the knee Stuart Weitzman boots with pencil skirt and silk shirt to the office!


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