How to wear knee high boots

Nikki ParkinsonFashion, How to 88 Comments

Don’t get me wrong, I’m not abandoning my love of the ankle boot any time soon (if you’d like tips on how to wear those, check out this post from last year) but I’ll always have a soft spot for a knee high boot.

I blame it on those white knee highs that Sally Boyden wore on Young Talent Time back in the day. I’ve coveted knee high boots ever since … almost as much as I’ve coveted white roller skates. Thank-you very much Xanadu.

I currently own three pairs of knee high boots. One pair of new flat black boots featured here; one a heeled suede Jaime Mascaro pair representing my most expensive shoe purchase ever five years ago and a pair of tan flat Country Road boots from about the same time.

Like many women, finding a knee high boot that fits around my calves – or should I say specifically my left calf – is quite tricky. I didn’t think my calves were overly large until I started shopping for my first pair of knee high boots 12 years ago.

After many a ugly step sister moment of trying to squeeze into too small a boot, I worked out what I had to look for before enduring the humiliation.

What I hunt down is a panel of stretch fabric – material that blends in with the main boot fabric so as not to bring undue attention to my fatted calves.

Others in a similar situation to me look to wide-calf boot specialists such as Duo Boots. My blogging mate Melissa from Sugercoatit wrote a couple of posts last autumn-winter offering up more shopping suggestions. You can check those posts out here and here.

My hot tip to you is if you’re on the hunt for a pair of knee high boots, do not delay.

Most Australian retailers only buy in a limited number of boots – particularly knee high ones – as our winter is such a short one and boots of this kind generally represent an investment purchase. You don’t want to find yourself in a situation where you’ve tracked down your dream boot only to find your size is no longer available.

My second hot tip is if you’re spending a decent amount of money on a pair then opt for a design that is classic in style. A good boot just gets better with age but these assets will mean nothing if the style is out of date the moment spring clothing hits our stores.

Buy wisely.

Here’s a selection of knee high boots any of these would remain your wardrobe friend for many winters to come. Oh and tan, nude and black are my picks for wardrobe longevity and outfit versatility.

Knee high boots AW14

1. Zoe Kratzmann boots $399 | 2. Target boots $59 | 3. Maria Rossi boots $379.95 | 4. Maria Rossi boots $299.95 | 5. Wittner boots $269.95 | 6. Ivy Lee Copenhagen boots $399 | 7. Diana Ferrari boots $249.95 | 8. Trenery boots $299 | 9. Django & Juliette boots $299.95

At a loss on how to wear knee high boots?

There are two main options – the tucked-into-jeans-look and the-worn-with-a-shorter-dress/tunic-look.

The knee high boots and jeans look

For a jeans look, those jeans need to be streamlined around the calves and ankles. No puffing above the top of the boot or you’ll risk being cast into the next Pirates of the Caribbean movie.

Balance out that streamlined bottom half with something flowy or with movement on top. Our good friend Nina Proudman masters this well with a tan boot.

The below outfit example is a little less boho but you get idea about balancing out our bottom and top halves to add interest to our outfits.

How to wear knee high boots with jeans

1. Blue Illusion jeans $199.95 | 2. Blue Bungalow shirt $109 | 3. Sussan bag $49.95 | 4. Eb & Ive scarf $29.95 @ Birdsnest | 5. Wittner boots $269.95

The knee high boots and dress look

This is a look that took hold in the 1960s – knee high boots worn back with short swing and shift dresses and coats. It’s these style origins that this outfit below takes its cue from.

The key to making it work in 2014 is to always have a little bit of leg showing between the top of the boot and the bottom of your dress or tunic. Leggings or thick tights are very ok. This gap between boots and frock helps to balance out the whole outfit.

How to wear knee high boots with a dress

1. Witchery dress $129.95 | 2. Country Road boots $299 (currently on sale for $224.25) | 3. Target coat $69 | 4. Trenery handbag $299 | 5. Metalicus ponti pant $149.95

Want more styling inspiration? I’ve started a board on Pinterest dedicated to knee high boots.

So tell me, would I find knee high boots in your wardrobe? Looking to buy a pair this season? Or sticking with ankles?

PS. My blogging mate Sonia over at Sonia Styling has written a post today about how to wear ankle boots. Check it out here.

PPS. As it’s ANZAC Day in Australia tomorrow, I’ll be spending time with my family. I’ll be back on the blog Monday with a new Model and Me post. In the meantime you can follow along on Facebook or Instagram for an #everydaystyle update.

Comments 88

  1. Hi Nikki, great read! I have both black and brown boots and my question is when do you wear brown? I almost always go for black as they seem to go with everything. Can you give me some pointers for choosing the brown over black?

  2. I have a pair of flat black suede boots that are just ABOVE the knee… I love them dearly but how to wear them???

      1. Thanks Nikki! Looks like I’m going looking for a shorter skirt/dress… how short can I go at 49 years old!!??

  3. I have four pairs of knee high boots in my wardrobe – black flats, black heels, brown flats, brown heels. LOVE my knee high boots. The black heels are my fave – I think they’re Nine West from five or six years ago, and they’re the most I’ve ever spent on a pair of shoes. Miraculously, despite my foot size increase over the two pregnancies, they still fit.

  4. I had been looking for my perfect black knee high boots for ages, even in the off season … while I had thought of never finding them, I went past a shop and there they were, my perfect pair, AND on sale with 30% off. They are now in the wardrobe awaiting Mothers Day 🙂

  5. Loooooove the outfits you have put together here. Very nice. And thank you for including the links to those posts. They have become such a resource for women looking for boots that fit.

    You’re soooooo right, a classic boot can be worn year after year after year. Especially if you live where we do!

  6. I have the most wonderful pair of knee high boots with a small heel that I bought 5 years ago in BabyMac country – I knew that I would find some in the southern highlands that were suitable for my sturdy calves. In fact the shop had a whole section for wider calves!! They are german, Ara, built to last and have seen UK puddles and even occasional snow on holidays every year since – so glad I invested.

  7. I love longer boots and have a trusty black pair along with tan ones. The tan leather ones have clever elasticated gusseting as part of the design and they are the most comfortable boots ever. I bought them in the UK but frequently got lovely comments about them here in Australia last year. Wish they made more calf friendly ones here! Love your styling arrangements with the boots too!

  8. I am dreaming of the day when I drop a few kilos and can pick up a pair of skinny jeans and knee length tan boots! Not sure if my short pins will ever be able to pull off the look though…. Oh and haven’t personally tried these guys but they do a wider calf boot too (various size options)

  9. I still haven’t found the perfect boots for my calves. I used to have a great shoemaker that would alter any boots I liked but I haven’t had any good knee highs in a few years – need to find myself some.

  10. I would have the opposite where the boots would swarm my calves and bunch at my feet and made me feel like I was wearing Gum boots. For me a zip on the side really works a treat. I have a tan pair of flat knee high boots and some Kumfs/Zierra Flat black knee highs that served me well on a trip to London and Paris 4 years ago. Love all your choices and styling arrangements. 🙂

  11. You will find a pair – a lot like the Diana F boots (pic 7). Sadly the zip has gone. I bought them in special on a mid winter holiday in Qld a few years ago. Now I live in Tassie which means boot wearing 10 months of the year!! I’m hoping my cobbler can fix them…it’s true love…

  12. I have the same problem with my left calf. I was told to go up a size in the boots as they add a little bit more room to the width with each size and then wear thicker sox. I actually wore my tan boots with a dress and jacket today.

  13. Super early start today – so only just reading today’s post. So excited to see advice about knee highs! Have 2 pair Diana Ferrari black knee highs 1 with heels and one flat. I work in an office with tiled floors and hate hearing myself clomp around in heels – hence the flats. But could not resist the third pair of flats – found them on sale last Nov for $75 down from $300. They are Earthies Chara – have been waiting sooo long to wear them. Not long now till our short Qld winter!

  14. Nikki I am looking for knee high boots the colour of 4, 5 or 6. For others out there Mountfords also have a lovely pair (Evette by Anne Klau $279). Sadly I have skinny shallow feet & ankles (width AA) and try as I might I cannot find a pair of narrow fitting boots – they swim at the ankles!! Any one got any ideas?

    1. I have read some of the reviews of the knee high boots on Ezibuy and there are several pairs where customers have mentioned them being too tight in the ankle, which may just suit you. Good luck.

  15. I read Sonia’s post and bought some ankle boots, and now I am inspird to get some knee high ones! I also struggle with ones that fit as I have chicken legs, so I will check out the brand mentioned in the comments. I did have a look around the stores today but a lot of them are huge heels and I need flat ones- even though I am in love with those tan Django and Juliette ones!

  16. Love boots. Although I’m not sure they’re the best look on my short frame, I feel like I have a great pair of long legs when I’m in boots!
    City Chic do wide calf knee high boots every year. I bought a black suede pair last year with a wedge heel and have been waiting for colder weather to pull them out again.
    Jo Mercer sometimes does a wide calf boot. I bought a flat heeled pair 8yrs ago that are still going strong.

  17. I love my knee high boots one pair I got re heeled last year but they were $400 boots so well worth it they are tan and very well loved and I also have a black pair and are so classic they will remain in my wardrobe till they fall apart but I do polish and look after them.I am on the hunt for a new pair of ankle boots as well in a more classic style that will last the distance!I have the opposite problem my calves are so skinny some boots look like pirate boots,I do love a skinny jean tucked into classic knee high tan boots,love that orange top Nikki!
    Have a lovely long weekend with your family and I hope you can rest and kick that flu Xx

  18. I love knee high boots so so so much. Currently I have a couple of different ones that have served me well but what I cannot manage to do for the life of me is tuck my jeans into my boots. I thankfully have quite slim calves and the jeans fit …. I just don’t like the look of it. I think because I am short it cuts me off. I have recently had some success with ponte pants the same colour as my boots. I am completely envious of people who can wear tan boots and jeans – such a great look.

    1. I know what you mean Kelly … I feel safer with a black ponte pant and a black boot but I do wear my tan ones tucked into jeans with some winter outfits – making sure there’s a good gap between the top of the boot and the top I’m wearing.

    2. I know what you mean Kelly … I feel safer with a black ponte pant and a black boot but I do wear my tan ones tucked into jeans with some winter outfits – making sure there’s a good gap between the top of the boot and the top I’m wearing.

  19. I love boots and won’t to go into how many pairs of ankle boots and booties I own (oohh look, I’m wearing white heeled brogues today!), but I will admit to having 3 pairs of around the knee boots: flat black motorcycle boots with chunky buckles around them that I bought more than 15 years ago (paying ME money on cost per wear!); high and thick heeled black super soft suede boots from Spain which have fine leather laces that criss-cross around the legs and tie behind the knee; and red cowboy boots I bought in a second hand store in New York.

    I can safely say I have gone for the flashy over classic styles, but have pretty much avoided ‘fashion’ and have bought what I loved. If I’m spending big I do prefer something more standout or special!

  20. Ah boots – my favourite shoes – knee high or ankle. Just love them! Have no doubt that I will be adding to my collection. Tan boots are my favourite – really love the Nina Proudman look.That first outfit you put together is to die for – seriously thinking about buying that orange top, scarf and bag. Love the less boho take on Nina’s look. It’s just gorgeous.

  21. I struggle with my loooooong calves. They end up looking like 3/4 boots, tight around my mid calf and billowing out where most people’s calf muscles would curve out. I also have skinny ankles (score!) so they tend to sag at the ankle too. Ankle boots are my only friend at the moment!

  22. I do not own ankle boots but looking into purchasing a pair. I have 3 pairs of knee high boots two black one with a heel and one flat. I also have a brown pair with a heel. Have always loved long boots since I was a young girl. I still remember the happiness when I received my first pair when I was about 9 years of age. V x

  23. Ahh… the knee high boot. I adore them – but like you – find that they are hard to fit around my ‘fatted calves’ (hilarious!!) I have a pair of gorgeous tan boots that have served me faithfully for 4 winters, they have been stellar, but – I need a new pair. Thanks for these tips! LOVE the Trenery ones, might have to check them out.

    I see boots as an investment piece and although I am a bargain shopping queen, I do not skimp on my winter boots. LOVE this.

  24. right on subject nikki! … loved knee high leather boots since the 70’s …
    always worn them, wear them as a constant in winter … currently I have three pairs d/ferrari black flats with that said elastic … perfect casual lifestyle of mine<3 … a black suede pair j mercer, with wedge gorgeous and still stroked! … also a Spanish flat pair which are from the 90's and I still wear them they are wider at the top good for over jeans they are dark brown love, love, love!!!
    might have to find a new pair this year just for keeping up appearances!!
    my legs are quite long so accentuate the positives I say! … v good post thans nikki lol m:)X

  25. As happy as I am to see Spring arrive here in the northern hemisphere, I am mourning having to pack away my beloved knee-high boots. I will see you in six months, my friends!

  26. I have the opposite problem with boots. I have no calves, so finding boots to fit is almost impossible. I stumbled upon duo boots a few years back and was so excited to get a pair of boots that fit me like a glove. Expensive, but they are great quality.

  27. I’ve always struggled finding knee-high boots that are more cowgirl than Pretty Woman, but I think this season could be the one! I’m alway searching for a country-inspired boot, and I’ve definitely found a few that could work in my wardrobe!
    Those Trenery and Django & Juliette tan boots look perfect! Thanks for the tips, Nikki!

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