Men love thigh high boots because they accentuate the legs, making them look longer. Plus thigh-high boots usually have a heel, sometimes a very high heel and this is often a great attraction to men. The thigh-high boot gives a look of strength and power to the woman. Making her look taller and dominant. Which a lot of guys like. Also, over many years on TV and in movies, so many of the sexy women are often seen wearing thigh-high boots and all the associations men have with seeing women wearing them.

Not just the stereotypical pretty woman in her PVC thigh high boots plying her trade for customers as a Hollywood hooker. Although sales of thigh high pvc ‘hooker’ boots went through the roof when that film came out – thank you Julia Roberts!

But even in the latest blockbuster, the new wonder woman movie, Cheetah (the bad girl) has a lovely pair of caramel coloured thigh-high boots on. Which no doubt implies she is ready to not only kick wonder woman’s ass but also get down and dirty with her. Whilst also looking totally sexy and cool in them.

History Of Thigh High Boots

Originally thigh high leather boots were designed for men. Back in the sixteen hundreds they were perfect to wear riding horses. It took a few more hundred years to think of leather chaps. Back in those days women werent really expected to ride a horse and if they did they rode side saddle with huge flowing dresses. Men on the other hand rode everywhere and needed to protect their legs and leather thigh highs provided the perfect answer. They were used by soldiers (and pirates) a lot too. Again these tended to be mainly male jobs.

So over the centuries, the role of the thigh-high boot not only changed (we ride a lot less these days) but also the gender most likely to be wearing them. When was the last time you saw a guy walking down the high street in thigh high boots? Exactly!

It wasn’t until the 1800s that some prostitutes began to wear leather thigh highs. Perhaps taking them as payment from their customers. Or even more possibly pinching them as they had no other footwear! I suspect that they soon cottoned on to how popular they were walking the cobbled streets in black leather thigh highs. It was considered totally shocking to see a lady dressed in what were clearly men’s’ clothes and therefore the thigh-high boot developed a bad reputation as ‘naughty’ garments for young ladies to be wearing. But those early prostitutes couldn’t help notice how many of their clients enjoyed them wearing them, so they stuck around long after we had all stopped riding everywhere on a horse. I don’t think there has been a pantomime without someone wearing them. It was certainly one of the reasons I liked to see them . Couldn’t get enough of captain hook slapping his thigh in his gorgeous leather thigh-high boots! – or is that just me?

Even so thigh high leather boots very much remained on the low key. They grew quietly in popularity right through the 40’s and 50s in naughty night clubs and all the black and white fetish photographs that were being taken discreetly, especially in America.

It wasn’t until we hit the 1960s before kinky boots were everywhere – not just worn by ladies of the night!

It was with the development of PVC and the mini skirt that the thigh high boot came out of the closet and begun appearing on your local high street

Avengers Kinky Boots Song 1964

These boots were made for walking

If you were a kinky pop singer, or a dominatrix space queen you needed to be wearing kinky long thigh-high boots.

Nancy Sinatra – These Boots Are Made For Walking 1966

Even though the mini skirt became a little bit longer in the 1970s it still looked fab with thigh high boots.

The eighties and nineties saw so much leather everywhere and it was perfectly natural to wear long leather boots with your leather trousers. And of course, that naughty Hollywood hooker, played by Julia Roberts was everywhere in those long PVC thigh-high boots.

By the 21st century leather, faux leather, latex, and PVC is being worn everywhere and by everyone. So of course tall thigh-high boots are also everywhere on the high street and online. Most shoe shops now sell at least over the nee boots as well as thigh-high. They have become a must-have for most wardrobes everywhere. Even my auntie has a pair of thigh-high leather boots which she often wears to go shopping in!

Something tells me we are going to see a real increase in thigh-high boots as this year progresses. They make a real statement, are eye-catching and leg enhancing. I predict once our nations news girls start to get bored of wearing tight leather skits on TV they will soon be incorporating sexy, kinky leather thigh-high boots. You read it here first – this Autumn your TV news or weather girl is going to be standing there in some gorgeous thigh highs-i cant wait!

What Do You Wear With Thigh High Boots?

Generally, its tight and sleek on the bottom and loose and soft on the top. So wear tight leather, leather look leggings or tight stockings/tights on your legs. Then pair this with a short skirt, not too tight and a loose fitting top. Maybe lace or wool if its the winter. Blue denim trousers with leather or suede thigh highs is a great look and not too trashy. I like tight leather look leggings and thigh highs in the same colour to help make my legs look longer than they are. Then on top a loose fitting blouse or even a baggy t shirt can complete the outfit. Thigh high boots also look great with a jacket too. Obviously I am going to say the more leather you wear the better. But if you havent worn thigh high boots before maybe go with some suede ones and even some of the fantastic pastel colours – pinks, wines or browns and caramels before hiting the streets in patent black or red kinky boots!

How do you wear thigh-high boots when you’re short?

Tip 1

The key tip here is to wear short skirt or shorts so there is as long a gap between the top of the boot and your hips as possible. That way your leg will look taller than it actually is

Tip 2

Wear trousers or leggings in the same colour as the boots so again you create a long looking leg from top to bottom

Tip 3

Wear the high heel option. So many thigh-high boots do of course come with high heels3-4 inch plus. These can be tricky to walk in if you are not used to it but then go for a platformed heel making you look even taller

Here Are Some Of My favourite Thigh High Boot Styles To Buy Right Now

Can Men Wear Thigh High Boots?

I must admit you don’t see many men wearing them down the high street. But that doesn’t mean they wouldn’t love to wear thigh highs!

Funnily enough, the thigh-high boot was originally designed for men to wear about 350 years ago. Tall leather boots were perfect protection for men riding horses and perfect footwear if you were a soldier or pirate. Look at a picture of a dashing cavalier and he will usually be wearing thigh-high leather boots. But not usually with 4-inch heels!

I’m guessing there are some guys about who have a secret cupboard with a pair of thigh high boots in. And just now and again, when they assume no one is looking they might get them out, dust them off and slip them on. Feeling them all the way up their legs and maybe they might even take a few steps, tottering in the heels as they walk up and down the hall in them. But its all just between them and their boots!

Where they have really taken off for men is with the fantastic kinky boots phenomenon. I remember seeing the BBC TV documentary about a northern shoe factory on its last legs (no pun intended LOL) and then the owner discovering the demand there was for well-built leather thigh-high boots especially by the drag queens, and CD men out there. This serious documentary got taken on by Hollywood of course and a hit movie and west end musical was born. Its great entertainment and certainly opens the doors for many guys to get those thigh boots on-the taller the better.

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Just Some Of My Favourite Thigh High Boot Moments

Superman 2

I loved seeing Sarah Douglas in her famous pvc thigh high boots in Superman 2. Such a wicked smile too!

Julia Roberts In Pretty Woman

Ofcourse I have to include Julia Roberts wearing those sexy PVC thigh High boots in pretty woman. They were everywhere back in the day. And yes I had a pair too!


Malin Åkerman as silk spectre II in this graphic novel film adaptation has a great latex costume and she certainly pulls it off with what look like latex black thigh-high boots – better than Catwoman I’d say! The movie wasn’t to everyone’s taste but I liked it!

Bridget Bardot

She certainly wore thigh-high boots a lot. Not so much in her movies but in her real life and some of her music videos- Like this one – Harley Davidson for example it doesn’t matter that it’s in french. And Viva Maria whilst no thigh-high boots there are some sexy leather boots she wears in the stripping scene and I like this movie!

Sophia Loren

Such a glamorous and beautiful woman. I can’t say I loved her movies but she wore some great fashions of the time. Including thigh-high boots in this movie, Arabesque (1966) and she wore some lovely leather in the millionaires


Lt Uhura Star Trek-Original Series

One of my first encounters seeing a woman in thigh high boots was watching the original series of star trek. I used to watch it with my dad many years ago. I remember the alternate universe episode where they all wore so much sexier costumes and especially the women who all wore thigh high leather boots. The boots also appeared in a couple of later episodes where the klingon women wore thigh highs and also a romulan commander. Who knew star trek could be so sexy!

Sybil danning

Tall blonde dominating and running around in tight black leather and silver thigh-high boots your thing? Well check out Sybil Danning’s the phantom Empire (1988) – terrible movie but great outfit or Battle Beyond the Stars (1980) – better film great cleavage lol. But it was her silver thigh highs that caught my eye.

The Three Musketeers

I had to include some guys in thigh high boots! Now to see men in thigh highs you need to watch old pirate movies or the musketeers. These 3 seasons from the BBC from a few years ago did have the men wearing quite a bit of leather and yes lots of thigh-high boots to enjoy. Now if only we could bring back such fashion again!

Obviously I could go on and on there are so many thigh high boot moments. I havent even the many pop stars who strut the stage in thigh high boots – Pussycat dolls, Rihanna, Beyonce and J- lo to name just a few. Maybe I will cover popstars in thigh high boots in another blog!

In the Meantime get shopping for some sexy thigh high leather or PVC boots and grab yourself some great boot moments from the DVDs I’ve mentioned

5 thoughts on “Why Do Men Love Thigh High Boots?”

  1. Ohhh my, I do LOVE a pair of Thigh High Boots!

    You’re exactly right Mrs L, a woman wearing a pair of luscious thigh high boots will always get my attention. Team it with Leather, Latex, PVC and Fishnets and I’m your to play with!

    1. Thanks for your comment Tony x
      What man doesn’t love thigh highs on a woman? have you got any favourite thigh high boot scenes/ women you enjoy watching?

  2. HIDE & SEEK
    Thank you for the photographs of you in boots: stylish and stunning.
    Boots and gloves can cover a little bit, quite a bit, most and then nearly all of the limb — leg or arm — they embrace. And they can fit snuggly or more loosely. They hide in hide the arm or leg making a distinction between the covering and the uncovered. So there can be a glimpse of a thigh, even a glimpse of stocking (why not arm stockings?). There is a kind of game of visual hide and seek with these garments. And then they can be see-through or seen through by design. Then you have the fastenings or not. And, with regard to boots, heels — height and thickness — and platforms. There is something ever engaging about boots and gloves.

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