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How To Wear Over The Knee Boots

Updated on November 16, 2011

Do you want to know how to wear over the knee boots, without looking like a pirate? This article will guide you through both the right ways and the wrong ways on how to wear long, leg hugging boots and hopefully prevent you from looking as though you've lost your ship, lost your client or even ... lost your marbles.

Unfortunately there's still every potential that someone somewhere will still prefer the frills and flounce that go on to project a stylish appeal than it will a badly thrown together look but - that's down to the reader.

If you enjoy looking unique and carefree, that's fine. If you prefer to learn how to wear over-the-knee boots in a manner befitting both your age range and current trends - read on.

Getting the hang of wearing long and lengthy knee boots is easy, once you know how. Unfortunately, what's even easier is the fact that you could end up looking like you're out in fancy dress or worse ... like a dominatrix. Unless of course - you are out for a night of costume tomfoolery ...

In the case that you're not up for a night out dressed like an extra from a Robin Hood movie, then following a few simple rules will go a long way to helping you look hot, happening and on trend. Over the knee boots wax and wane as the years come and go and whether you like it or not, they never quite go out of fashion. And of course it helps if you're a youngling. But - if they're good enough for Madonna at 51, then they're good enough for the rest of us little people - right?!

Let's face it, long and high boots are incredibly hot. But they can, on the wrong legs and coupled with a lack of style, look incredibly silly. I own a pair, though mine are flats.

I'm tall enough for one thing and for another, I'd break my neck in heels. I'm all leg and no body and Nature blessed me with an innate talent for falling over. And that's when I'm in barefooted.

So, knowing my limitations, I stick to footwear that tends to help me remain vertical. However, I'm not your average female. My sister wanders around in skyscraper heels in the same way I wear slippers. And she never hits the deck. In fact, most women I know are comfortable in heels so if you can walk in them - don't limit yourself to a flat pair.

Over the knee boots do take some carrying off and they're not for everyone so, if you're confident, carefree and fancy a pair, take a look at the ones with heels. If you're like me, flats are best.

Either way, here's a few starter tips when it comes to wearing them:

  • however gorgeous you are, you're not Julia Roberts and your life is not Pretty Woman. So never ever wear them with bright, tight, butt-hugging lycra mini-skirts
  • black is best. If you're more conservative, buy brown but black always look a lot hotter and will match with anything you wear on your legs
  • unless you really do love the old 80's flambuoyant look, avoid the ones that look 'piratey'. Frills and flounces on your top half are also a no-no
  • some styles can look more like they're boots made for a dark dungeon somewhere (you know what I'm talking about ... ) so avoid them like the plague. Unless you do frequent such places ...
  • you can buy leg-hugging boots or softer, looser styles. Whichever you buy or own, consider what it is you're wearing on your legs. Tighter styles are harder to wear over jeans for e.g. - unless they're skinny jeans

Knee High Boots

The knee high boot is almost the same - just shorter. Still as trendy and hot looking, they finish just on or below the knee. I've brought them into this article simply because you can adapt any of the style tips to suit the knee high version.

Again, it doesn't matter whether they're slouch boots, flats, stiletto or wedge style, you'll look just as good wearing the shorter version as you will when wearing a pair of over the knee boots.

The same rules apply and whilst some may believe that longer length boots are not for anything other than dark and shadowy corners, they'd be a long way from being in the right. As long as you tone down other areas of your overall style, you'll look great without looking silly.

Long boots are here to stay.

Over The Knee Boot Styles

Outfit types and boot styles are part personal taste and part confidence. The stiletto kind (for e.g.) really do need a confident bod to carry them off with anything approaching aplomb so - do be warned - if you lack confidence, don't bother buying or wearing them.

That said, depending on what you team them with, you will only look nothing short of chic and stylish. Also, now's a good time to mention age ... remember how old you are. A horrible fact of life but some styles really are best left to those that gravity and laughter lines have yet to visit.

And having brought up the age factor - here's some styles that can be adopted and adapted by the pretty young things among us:

  • a pair of tweed or heavy fabric shorts, teamed with a pair of ├╝ber cool tights look great with over the knee boots
  • a tunic style mini-dress, again with some snazzy tights, and layering and/or a shrug
  • a thigh skimming top, worn with some figure hugging leggings - jeans, leather or shiny ones - and a pair of flat or slouch boots is a great look
  • a mini-skirt, semi-semi tailored, opaque tights, with some layers or, for a more contemporary look, a smart jacket - a pea-coat or blazer type
  • a boho dress, cut on the bias, floaty, lots of movement, some stylish accessories such as a large slouchy bag

For those of us that are creeping towards middle age, don't despair. There's still a style or two that will both suit and flatter you ... being a bit past your twenties doesn't mean you can't wear long boots. You just have to be a little more - careful!

  • skinny jeans! A gift to women of any age. A pair of skinny jeans, matched up with a loose tunic top or a raglan sleeved knit
  • leggings - yes, you can wear them. Again, teamed with something thigh skimming such as an A-line mini dress. And don't be afraid to try something dark and slinky - but equally, avoid too much black or dark color matching. Add a splash of color with a natty scarf or accessories
  • go tailored - another great look is a fitted skirt, a well cut shirt, and mid-thigh length tailored coat. Add in a chunky bag and you're set to go
  • try wearing a soft, loose knit, a pair of skinny jeans or leggings and if you're lean or slim, cinch in your waist with a belt
  • for those that like to hide a little more under looser clothing, a long, semi-fitted over shirt will give a casual appeal

Six Style Tips To Remember

Finally, six tips for wearing over the knee boots. The main 'don't do' rules are:

  • avoid anything patent or, if you love the shiny look, don't wear the same on top
  • don't go for anything with too many laces or sky-high heels
  • the kind that have slashes of leather or material missing - avoid
  • don't wear under normal jeans
  • never wear with tight 'make your mother weep' mini-skirts
  • never wear too many colors - keep the palette soft and co-ordinating

For those that are supremely confident, experiment with color. Red and purple over the knee boots are pretty hot and if you've got tons of confidence, consider something in an animal print. Don't just limit yourself to black - or brown - if you've got a lot of buoyancy and poise.

And so - now you have some idea of how to wear knee high boots. With a little flare, add in some confidence and an eye for what suits you and what doesn't, you should have no problem working out what to wear with your boots - and what to avoid.

Boot Stroot - Video Guide

Long Boot Essential

An added extra to all the above is a new product on the market, the Boot Stroot. It's an absolute essential if you are a fan of long boots.

It's a fabulously simply yet highly effective boot accessory, and it really does do exactly what the advertising says it does.

I've been testing this product this last week and I have to say that I'm highly impressed. The Velcro 'cuff' holds onto your jeans at the ankles, allowing you to pull your boots on without creating that horrible looking gather at the knee.

It's also an affordable product, less than 10 bucks, and for those of you that haven't heard of it before - it's innovative and really quite brilliant. For my part, I don't care about the color, as you can't see the Boot Stroot once you have your boots on.

If you've gotten this far on the article, check out the site (link to the left) and consider adding a pair to your must-have accessories list.

Worth every penny.


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    • FlourishAnyway profile image


      5 years ago from USA

      Terrific hub. No one wants to look like a pirate. I have always loved boots.

    • profile image


      7 years ago

      Great article! Just curious, what make are the boots featured on the main page of this article - the first of the 8 photos? Been looking for a pair just like that forever...please e-mail me at

    • profile image

      un known 

      7 years ago

      as you like

    • profile image


      7 years ago

      i have been trying to decide for over a month what colour to wear with my purple over knee boots as i didn't want to wear black i have decided to go with leopard print legging thanks to you

      thank you

    • smcopywrite profile image


      8 years ago from all over the web

      i love the look of the over the knee boots and the pull on style. however, because of my instep, i cannot wear any pull on shoes or boots. great hub and interesting information

    • BMG profile image


      8 years ago from timor laste

      great for who like to wear knee high boots...

    • mysisters profile image


      8 years ago

      Great Hub. I love knee high boots! You can wear them with so many different outfits. I like them especially with skinny jeans for around the town or a night out.

    • profile image


      8 years ago

      Hello, I am 5'1, can i wear over-the knee boots? i really like it.

    • profile image


      8 years ago

      I can't walk in heels either LOL. I've never seen flat heeled boots but I want to look for some - high boots are so sexy!

    • Tati Irodova profile image

      Tatiana Irodova 

      8 years ago from London, UK

      very good read, awesome hub, i've got 4 pairs of over the knee boots (cant get enough of them!) and everything you wrote here is true. Great advise! x

    • profile image


      9 years ago

      Luv 'em with skinny jeans...

    • frogdropping profile imageAUTHOR


      9 years ago

      Ghost - lol just don't ever try to replicate the Pretty Woman look ... not a good idea. And thankyou :)

      marcel - yep ... treat yourself. But buy the perfect pair for you :)

    • marcel285 profile image


      9 years ago from New Zealand

      Awesome hub, i loved it..Now to get some over the knee boots

    • Ghost Whisper 77 profile image

      The IGNITER vs Corrupted Governments 

      9 years ago from The U.S. Government protects Nazi War Criminals

      Every time I see them they remind me of "pretty woman." ;)

      Cute with jeans or a long sweater dress! Thanks for the hub

    • frogdropping profile imageAUTHOR


      9 years ago

      Justine - yes it's a word. Loosely translates into 'frogdropping' :)

      Fishtiger - in bad weather I wear boots similar to you. I don't bother with how I look when it's nasty out so wear your hiking boots with pride ... I do ;)

      Smireles - there's nothing wrong with dreaming eh?! :)

    • frogdropping profile imageAUTHOR


      9 years ago

      Keira - if you fancy trying some, go for it. Don't be shy. However, if they'd make you feel uncomfortable, don't buy any. Clothing is supposed to make us feel better, not worse!

      And yes, I'm back in Lisbon. No snow but lots of rain instead. It's quite chilly at the moment, though nothing like the weather I left behind in the UK :)

      And don't worry about reading my hubs, you really don't have to. I'm full up on them and there's far too many to try and catch up with. All the same, thankyou for trying and no worries about commenting or not!

    • Smireles profile image

      Sandra Mireles 

      9 years ago from Texas

      Very enjoyable read and although I am far beyond all that I still like to look and dream.

    • fishtiger58 profile image


      9 years ago from Momence, Illinois

      Great article frogdropping you never fail to make me laugh. However I am more the hiking boot type of female an will stick with that. Thanks for an enjoyable read.

    • profile image


      9 years ago

      Hahaha. You flatterer....(is that a real word?) :)

    • keira7 profile image


      9 years ago

      Hi my dear Frogdropping, one of my sister love this sort of boots. I liked them too but its not really me. I am to shy. But I must admit that over the knee boots are beautiful. Mmm actually I probably will give it a go. Just looking the pictures again and I think I am tempted.:) My husband will be happy.:) Thanks to you my friend.

      BTW I did read your other hubs and rate them up. Actually, I try not to write to many comment. Just read hubs and rate them up. Its just I have read on the forum that hubbers should not write small comments. I dont know, I am confuse. Anyway i will say the magic sentence that everyone use. The sentence "is great hub very good info.":) Have a lovely weekend my dear.:)

      Ps: Are you in Lisbon? because I was very lucky to travel before the snow covered the all of UK.:)

    • frogdropping profile imageAUTHOR


      9 years ago

      apricot - they've never really gone out of fashion. They ebb and flow, as time goes by. I wear mine as and when, have done for years, though I've gone through a few pair over the years! And thankyou :)

    • apricot profile image

      Bengali Bratisha 

      9 years ago from Italy

      Fascinating read! I'd never considered over the knee boots before, in fact are they in fashion? Agh, I'm so out of touch! I'd go for the flat heel ones too - I just feel conspicuous clopping around like a horse. Gosh, you've really got me off thinking about this one..I am a staunch Doctor Marten's girl myself but perhaps it doesn't hurt to deviate every once in a while...great hub!

    • frogdropping profile imageAUTHOR


      9 years ago

      Justine - lolol! I bet ;)

      I'm glad you like them - I enjoy writing them. I have others in the pipeline but I try and stick with clothing etc that will be around for years or have been already. Otherwise my hubs would go out of fashion too ... :)

      And for sure you're a beautiful woman so shut up ye - you've nothing to cry about in the looks stakes lol! I bet you could wear a shapeless sack and your beauty will still be clear! Ohhhhh to be so pretty as you, minha amiga!

    • profile image


      9 years ago

      the reason I exist is over the knee boots, and a mini skirt....

      :) I love your fashion hubs, they give me hope that I too, can look sexy and not always ...momish...

    • frogdropping profile imageAUTHOR


      9 years ago

      ethel - I think my gran wore them way back in the 70's. They've been around a while, in many style :)

    • ethel smith profile image

      Ethel Smith 

      9 years ago from Kingston-Upon-Hull

      Wore these many years ago. Ahh

    • frogdropping profile imageAUTHOR


      9 years ago

      Dim - I love my boots and thought I'd share some ideas. Like you I'm way beyond the young stuff but I wear mine regardless - I just don't go out as 'mutton' ;)

    • Dim Flaxenwick profile image

      Dim Flaxenwick 

      9 years ago from Great Britain

      I think I should print this hub out and keep it with me when shopping. Great advice. I too fall over easily (without alcohol, even) and I'm way past the age for many of these styles. My daughter looks fantastic in animal prints, stilletto types. Makes me sick,.Great hub. Thanks

    • frogdropping profile imageAUTHOR


      9 years ago

      Enelle - I like mine. Had them about three years now, to replace a pair I had for a long time. The one thing I've always spent decent-ish money on is footwear. I don't have many shoes etc and my preference is boots over shoes but I do enjoy wandering around in skinny jeans and over the knee boots :)

      And thankyou - much appreciated ;)

    • Enelle Lamb profile image

      Enelle Lamb 

      9 years ago from Canada's 'California'

      I would love a pair with a lower I'm looking through you selection ;) - great article my dear!


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