When To Wear Ankle vs. Knee-High Boots
posted on March 11, 2013 | by Amanda Holstein
Once ankle booties came on to the scene, deciding between them and my always reliable knee-high boots became somewhat of a dilemma. And now that most of us own both, I thought I’d break it down and show you when to wear ankle booties vs. knee-high boots, depending on the shape and color of what you’re wearing. I see knee-high boots worn all the time when ankle booties are actually the better choice, so let me prove to you just how versatile your ankle boots really are. Now, keep in mind this guide is just my personal opinion. If you disagree, let me know in your comments (nicely, of course) below!
Dark Skinny Jeans:
Whether a deep burgundy red, or a classic blue jean, darker shades look great with both ankle and knee-high boots. Often times, knee-high boots can cut your leg in an inopportune spot, making you look shorter, but when paired with darker skinny jeans, you avoid that issue.
Boyfriend Jeans (or any non-skinny jeans):
I see way to often baggy jeans paired with knee-high boots. It’s an honest mistake, but listen up people. Knee-high boots were made for fitted jeans so you can avoid that bunchy area around the knee. Save your boyfriend jeans for ankle booties and make sure to roll them a few times using this handy-dandy guide :).
Light Skinny Jeans:
Now, this is debatable. But the way I see it, white or light colored skinny jeans are not meant for knee-high boots. I feel that knee-high boots cut off your legs more harshly in light colored pants, making you look shorter. Since light jeans are already not very slimming, shortening your legs with knee-high boots can make that effect even worse. I say it’s best to pair your white jeans with ankle boots to elongate the legs.
Printed Skinny Jeans:
Since printed skinny jeans are very busy, pairing them with a tall boot can distract from the pants and just make it feel like there’s too much goin’ on. I think ankle booties are a great option for printed pants because they allow the pants to be the focal point of the outfit.
Now, my southern friends with their cowboy boots may not agree, but I’ve always felt that knee-high boots should never be worn with shorts. The two together can sometimes be a bit too much. Plus, the proportions cut your legs off in 2 different spots, again making you look shorter.
Midi skirts are already difficult to style and can often make you look shorter, so pairing them with ankle boots is a much better option. That way you can see the thinnest part of your legs and keep them looking long and lean.
For the most part, straight mini skirts or dresses go with both ankle and tall boots. To make sure the look isn’t too revealing, pair your mini skirt with a top that provides more coverage. A long sleeve sweater dress or something not too form-fitting or low-cut would work well with the knee high boots.
Flowy or A-Line Mini Skirts:
Both ankle boots and knee-high boots work great with flowy dresses and skirts. The loose fit makes either boot appropriate. Choosing which shoe to go for just depends on the look you’re trying to achieve.
Is this how you wear ankle and knee-high boots?
I think this is a really great post! I pretty much agree with what you wrote, which is funny because I only own riding boots, not any ankle boots. But now that I’ve read this post I realize that I don’t wear my boots with any of the things that you said knee-highs don’t go with. Now I am thinking I should probably get some ankle boots so I can wear more of my wardrobe in the winter :)
I love those brown riding boots! Thanks for laying down the do’s and don’ts
Love this! I actually have almost identical boots as both of these, and I often style them the same ways. Great post!
nancy @ adore to adorn Says
Yet another awesome post! I love the different comparisons you offer! Definitely an occasion for ankle boots vs. knee!
Shay Lianna Says
I totally agree with this! Though, I do admit to wearing pants that bunch around my knees under my tall boots, sometimes. It’s just that my pants always are looser at the bottom, so they are hard to keep smooth. So frustrating ;)
Emily | Sparkle Meets Pop Says
Love it! Ankle boots are on my shopping list, but I always wondered — how versatile would they be?
Kim teasdale Says
I love this post! My question is how do I know what colour boot to wear. I have ankle boots in black and brown suede material(couldn’t pass up the $17 deal) and tall boots in black square heel and brown with a wedge heel.
I am going on a trip to Chicago this summer and am considering some ankle boots instead of sneakers and flats. It’s going to be a trip with a lot of walking and seeing the city with friends, so I am looking for a ankle boot that is comfortable but still stylish with shorts and dresses (I will be going to Chicago in July).
Do you have any suggestions for brands or styles of ankle boots that might work well for me?
Amanda SaysPost author
Try ones with a lower heel. I’ve heard these ones by Sam Edelma. These Steve Maddens are a great option too!
Amanda, I wanted to check out the booties you recommended, but those links aren’t working for me. Do you have names or model numbers? Thanks!
Amanda SaysPost author
Hi Kacie! Sorry the links aren’t working but this post is a few years old so the items featured are no longer available. Feel free to email me and I can find you something similar to what you’re looking for! Thanks!
what i’m left wondering after this is where are your beautiful ankle boots from? as i’ve just seen the last of mine with an irrepairable hole in the leather!
Love these tips. I too sometimes can never figure out which boots to wear with what. I’ll definitely be referring to this guide in the future. btw. I love your blog so much. so informative for the twentysomething woman and beyond.. Keep up the wonderful work! xo!
I agree for the most part…personally I don’t like wearing tall boots in the warmer months, as I feel like too many people make egregious unseasonal boot errors in the summer. On that note, i disagree on wearing shorts with tall boots–i wear them with tights in the winter/fall constantly…they’re a big part of my cold month wardrobe rotation! Without tights, however, tall boots and shorts looks silly to me (see: egregious unseasonal boot errors).
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Nicole Maher Says
This is a very helpful post. Thank you so much. It was exactly what I was looking for!!
I’m loving those burgundy red jeans in the first example! Where are they from?
Amanda SaysPost author
Thanks so much! I love these pants – they’re actually corduroys! I got them from Madewell last fall so they’re not currently available, but I’m sure they’ll have something similar this coming season.
I heart those ankle boots! could you tell us where they`re from?
Amanda SaysPost author
Hi Yasmin! Thanks so much, I wear these almost everyday. They’re amazing. I got them from Madewell here: http://bit.ly/ZgRDNP
*cry* im a size 11, *runs off to stage protest at madewell*
Are they the barnyard boot at Madewell?
I think white skinny jean is the best pairing with knee boots, as you see those horse rider you will know.
Actually white or light skinny jean will expose weak point of your leg, that mean if your leg short or fat prefer you wearing black jean, and if your leg long or skinny white jean can make your leg even longer if you wearing a pair of flat boots or heel boots.
Amanda Gluck Says
LOVE this post!!
Good advice! It’s such a difficult balance, and often ladies get it very wrong. I wrote my thoughts on knee high boots – http://champagnespit.com/fashion-advice/what-to-wear-with-knee-high-boots
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The shape of your legs looks like mine — they are not straight, so I look weird wearing knee height boots because the boots emphasizes my bow shape legs. Sort of like how you look in the pictures with high boots
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I love those kneehighs, really stylish, those buckles are great touches!
I pretty much agree about them not looking so good with some below knee skirts, but not because the visible leg is covered in boots, more for a matter of style and color association, with some styles and colors of low skirt, I think it hits the nail right (how americans say), clearly you don’t want to show legs with this combo, in this case it is wrong of course.
I agree about those and most shorts (but maybe some Silvana Mangano styled shorts) and those type of printed trousers.
Not about white jeans, i don’t find them shortening or at least the knee boots don’t seem to worsen the effect the least bit more than the ankle ones, to me :).
Also not about boyfriend jeans, I think it’s a more casual style that I often see in winter, in my city, but most have a trick to tuck them even better (not that those little baggyness is bad, imho) so that they fit them almost like skinnies. It’s about accurately folding the jeans and then rising the sock over them. Could be a bit weird if they ask you to take them off (like you know the shoes off ruled houses, lol), but just pretend it’s nothing and that these people are used with the tricks of tucking boots :D.
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Where did you get the printed skinny jeans?? I LOVE them!
curious on where you got both of your boots?!?! I’ve been looking for a cute pair of riding boots and love the ones you have! thanks so much!
Love your knee high boots!! Who makes them? Where did you find them?
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Whats the difference between not to wear knee-high boots with shorts as you state, than wearing them with mini-skirts. Both cut proportions off at the same spots and legs look identical!!
Amanda SaysPost author
Good question! Shorts tend to be shorter than mini skirts and give off a more casual vibe. That’s why I prefer not to wear them with knee high boots, but it’s up to you!
Nancy Armstrong Says
Thank you for your helpful fashion advice. I am almost sixty years old, and bought a knit, straight, knee-length dress, which is casual. One is a solid navy dress, and the other is a green and navy stripe. Both have ragland sleeves. What should I wear on my feet? Do I wear short boots, or knee-length boots, cowgirl boots, or flats?
This was very helpful! Thank you
I have to have those ankle booties. I know you said they were by Madewell, but what style are they? The zipcode? Please, I have to find them
Amanda SaysPost author
Yes they are the zipcode bootie! They should still be available in stores if not online :)
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Where did you buy those knee high boots? I’ve been searching everywhere!!!
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Love this. I am literally going to wear a few of these scenarios
This week with this tx weather and my new boots and booties
I think your pictures and comments are spot on and super helpful! Is there any way that you could share more pictures of different style ankle boots with the correct jean styles. Some booties hit the ankle at different places and this changes the look– particularly with the rolled up jeans example. Could you share more pictures of rolled up jeans and various booties?
Thanks so much!
Amanda SaysPost author
Great question Jules! I can definitely work on a follow up post about this. Thanks for the idea!
Yes, great question! I have a pair of Clarks Artisan shoes called Alpine Andi in the purplish/grey color and I can’t figure out what to wear with them! Any help would be very appreciated. I loved this post!
I would wear them with a dark wash skinny jean. I also would wear them with leggings and a sweater dress. The dress option I would do black or grey and let the boots be my pop of color with gold accessories. Have fun trying new outfits.
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Oh No! At this moment I am wearing light skinny jeans with my knee high brown boots…. I always thought it made me look like a safari guide, but thought that was the style…. NEVER AGAIN! Just another excuse to buy more ankle booties! I love them!!!!!
Hi Amanda – great post!! I’d love to know the brand/style of ankle boots you’re wearing in this pic – they are so cute!
Charity Pereira Says
Hi There! Can you please please please let me know where the knee high boots are from?
I’ve been looking for some and they are perfect!
I wore printed jeggings today with black knee highs.. i can see now it may not be best, but I find they look good! Maybe because they are black?
I find it hard to wear ankle during the winter months here in Canada.. :(
Stephanie Jiron Says
I have been looking since last winter for riding boots that I like. I have to have yours. Where did you get them? I’d be eternally grateful!
A very informative post, thanks! Could I ask where you bought your ankle booties at? I have a horrid time finding ones that don’t gape dorkily around my ankles –have the same problem with knee-high ones, incidentally. :/
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I just look at the boots with such yearning. I have a short, very wide foot and there is simply no boot, ankle or tall, that would fit. There’s no fashionable shoe either, like pretty spiky heels or those sassy summer sandals. :-(
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Loved your post :)i was a bit confuse in dressing up with my boots but with all the suggestions you gave i’m gonna do it right…..:);)
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Great post! This is really helpful. I especially like the bit about cuffing loose jeans with ankle boots. It looks great – why have I not been doing that??
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Thank you for an informative article! I’ve just recently purchased a pair of ankle boots and have been wanting some ideas for how to wear them right.
I really love both of your boots? I have been on the lookout for something similar can you tell me what brand and style they are? Thanks! :)
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I actually don’t agree with most of these. The boots you’ve got don’t work with the pants, but many of the pants would absolutely work with other knee high boots. Definitely a lot of the styles you put together could work for a person who has that style or wears things that way. Basically, the only time a knee high boot does not work is when the jeans are really baggy. You’ve got a good example of that, but the rest is a little subject.
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Loved the idea of do’s and don’ts with photos. Only one I felt differently about was the white jeans. I too prefer them paired with the riding boots as opposed to ankle boots. I think the ankle boots might look better if the jeans were full length but the gap between the boot and hem is not that flattering, it seems to make your legs appear shorter? In saying this I must add that I really appreciated your advice and being able to see the comparative looks.
I have been looking for the perfect knee high boots, and those are beautiful! Could you tell me what boots they are?
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Ankle boots don’t always look as good as you suggest. I wouldn’t wear booties with:
– light jeans
– midi. It makes me look like a 1930s farm wife or something.
I might wear them with the following, depending on color, pattern etc:
– printed jeans (I think the boots look better in your example. Black boots even mo’ better.
– mini. If the shoes were a neutral color, maybe. I want the boys to look at my legs, not my shoes!
a man who knows better Says
You are wrong, the knee highs win every time
True! Except of the boyfriend jeans
I agree with all but the light jeans… I feel that the ankle booties make your legs look shorter. It may be the picture or the angle but I think the tall boots look better there! Just nicely disagreeing ?
Amanda SaysPost author
People seem to go back and forth on the lighter jeans too! In the end, it’s totally subjective so if you like it, go for it!
I agree with your observations on when to wear ankle boots. I love my knee boots but they never look good with midi-skirts or boyfriend jeans. Ankle boots to the rescue!
Great post! Very helpful comments about each look. Had to pin for reference :)
Thank you. I’m a ‘closer to being 40’ than a ‘twenty something’ but I work with a lot of ‘closer to 20 somethings’ and I love all of the business casual styles they wear. I’m pretty good at making the looks work for myself but I’m always ready for a bit of guidance when I’m worried that I’ll look like ‘that lady who’s too old for that outfit’.
I agree with this post. I love your visuals as well. I am on the shorter side – 5′ 5” and although I do like knee-high boots, the booties are much more flattering on my frame. I’m happy that ankle boots are in style and hope they stay that way.
Why are you always pointing the toes of one foot to the other foot in your ankle boot photos? It’s a very awkward-looking deliberate pose.
Amanda SaysPost author
Hi Bessie, That’s a good question and I honestly don’t know how to answer it. Posing it front of a camera can feel very awkward and uncomfortable sometimes — I’m certainly not a model!
Amanda SaysPost author
Could you be more specific? Thanks.
I love your photos! I would like to add that with a longer pair of leggings or skinnier and ankle boots, the pants look better rolled up at the bottom instead of going down into the ankle boots! The little bit of ankle showing helps set off and separate the pants and boots and really can showcase a gorgeous pair of ankle boots!
I really did agree with some of the choices.like printed skinny jeans would look better with knee-high boots and light skinny jeans knee-high boots!
I really did agree with some of the choices.like printed skinny jeans would look better with knee-high boots and light skinny jeans knee-high boots! But whatever we all have our own opinion.
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I like this post and mostly agree with your suggestions. The midi skirt especially. The only one I down-right disagree with is the knee-high boots and shorts. For someone who doesn’t like to show a lot of skin and have my legs outside, knee-high boots are the only way I’ll wear shorts. And I don’t find they look weird.
I know that many people feel that knee-high boots cut the legs off in a weird place, but for certain body types it adds the extra weight needed lower down to balance out the thighs and some woman have just enough height to not have knee-high boots make them look short. It all depends on your body type really.
Of course this is my opinion and I’m not attacking or criticizing your thoughts in any way. Just sharing my own.
Thanks for this! Believe it or not, I am 38 years old and have never worn boots until just recently. I bought both the the short and the tall ones and now I am addicted. Your post really helped me. :)
I love wearing tall boots. I wear with print leggings or mini skirts.the tall boots with black tights and mini skirt look real sexy
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Tip #7. Don t ever layer socks over your jeans when you re wearing booties. Unless they re jeggings and are very thin material, it will add even more bulk to your ankles. Just don t do it.
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Well, to be honest: I totally disagree with your choice. Almost always the long boots get along well with your outfits. Wearing those ankle boots with a midi skirt or skinny jeans make the feet look like being oversized.
I don’t have ankle or knee high boots.I mostly have over the knee boots.because I think they are better.
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This is great, I’m so glad I found this, because I am horrible at fashion. Tell me though, what if you are short and you have thick legs, even all the way down to your calves? I normally stick to long maxi skirts and knee high boots (when I can find some that fit my calves) in the winters up here in the northeast, but now I’m trying to get out of my comfort zone and try skirts or dresses that fall around or slightly below the knee. I am not sure if I should do tights with an ankle boot or a knee boot. I know cropped pants look horrible on me because I’m short and thick from the waist down, so the taller I can look the better.
Thanks for your advice! Even if I found you 4 years later!
Brenda R Hart Says
Love the article and I agree with most of it – except the bit about light coloured skinnys. White or light coloured skinnys pair really well with light coloured knee high or over the knee boots – think stone, gray, taupe, etc.
Thank you for your post. I share your opinions except the light skinny jeans. You are right if it is worn with a dark knee hight boots as shown in the picture it cuts the length of the legs. On the other hand, when it is worn with a little high heel lighter color boots such as light gray or winter white it works the same as darker jeans. Of course if only you want to have a second pair f boots for lighter colors. I invested one that is an average price from Marshalls.
Thanks for your post again!
fashion comes and goes, style has real staying power. Says
Apart from the printed/paterend jeans, although they look like fitness leggings, all the outfits look great with knee high boots. Ankle boots are best reserved for coated jeans, leather pants, leather look leggings.
Hello Amanda! Fabulous Post! I couldn’t agree with you more! I am short myself 5’3 so I struggle all the time with what I think might look good on me verses what really does! Lol Thank You! This post is Super Helpful! Have a Wonderful Day! Sheila 😊
Your friends from the south in all likelihood are wearing cowboy boots that hit mid to lower calf if they are wearing them with shorts.
George Louis Says
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Debra Wagner Says
I agree with all but 1.
The midi dress. The short boots look stupid, they cut your legs off make them look shorter than the long boot. Also no offense. You might want to learn how to stand. You have nice legs but you make them look bow legged and awkward.
I did enjoy all the other hints.
So you would pair boots with dresses that have the same cut off point as the shorts??? 🤔
Hey Amanda, Thanks for sharing this article, it’s very informative, the things you’ve mentioned regarding it is quite impressive, next time I’ll keep these things in my mind when I go shopping, keep up the good work, looking forward to more in future posts.
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Many non-skinny jeans look fabulous with knee high boots. It all depends on the amount of bagginess at the knees. Chrissy on Three’s Company wore boots with pants that way and it looked great!
Also, I love to wear knee high boots with shorts -and also dark tall boots with light or white jeans. Another important is the heel style, where a narrower chunky mid height or high heel always looks attractive. Finally, IMO full length boot zippers are the only way to go on tall boots!