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  1. March 11, 2013
    Ashley says

    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 :)

  2. March 11, 2013
    Shannon says

    I love those brown riding boots! Thanks for laying down the do’s and don’ts


  3. March 11, 2013
    Alyssa says

    Love this! I actually have almost identical boots as both of these, and I often style them the same ways. Great post!

  4. March 11, 2013

    Yet another awesome post! I love the different comparisons you offer! Definitely an occasion for ankle boots vs. knee!

  5. March 11, 2013

    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 ;)

  6. March 11, 2013

    Love it! Ankle boots are on my shopping list, but I always wondered — how versatile would they be?

  7. March 11, 2013
    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.

  8. March 12, 2013
    amanda says

    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?

  9. March 12, 2013
    Elle says

    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!
    elle x

  10. March 12, 2013
    jewel says

    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!

  11. March 13, 2013
    hannah says

    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).

  12. March 17, 2013

    […] boots or knee highs? Check out this post to know which to wear […]

  13. April 27, 2013
    Nicole Maher says

    This is a very helpful post. Thank you so much. It was exactly what I was looking for!!

  14. April 28, 2013
    Taylor says

    I’m loving those burgundy red jeans in the first example! Where are they from?

  15. April 29, 2013
    Yasmin says

    I heart those ankle boots! could you tell us where they`re from?

  16. May 7, 2013
    tight&skinny says

    I think white skinny jean is the best pairing with knee boots, as you see those horse rider you will know.

    1. May 9, 2013
      tight&skinny says

      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.

  17. May 8, 2013

    LOVE this post!!

  18. May 11, 2013
    Adam says

    Good advice! It’s such a difficult balance, and often ladies get it very wrong. I wrote my thoughts on knee high boots –

  19. June 25, 2013

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  20. June 27, 2013
    JJ says

    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

  21. July 12, 2013

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  22. July 16, 2013

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  23. July 26, 2013
    Antome says

    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.

  24. July 31, 2013

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  25. August 28, 2013

    I was recommended this web site by my cousin. I’m not sure whether this post is written by him as no one else know such detailed about my difficulty. You are amazing! Thanks!

  26. August 31, 2013
    Jennifer says

    Where did you get the printed skinny jeans?? I LOVE them!

  27. September 2, 2013
    Stephanie says

    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!

  28. September 10, 2013
    Helen says

    Love your knee high boots!! Who makes them? Where did you find them?

  29. September 14, 2013

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  30. September 24, 2013
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  31. September 25, 2013
    Nora says

    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!!

  32. September 29, 2013
    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?

  33. October 1, 2013
    Joanna says

    This was very helpful! Thank you

  34. October 3, 2013
    Debbie says

    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

  35. October 3, 2013

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  36. October 9, 2013
    Lisa says

    Where did you buy those knee high boots? I’ve been searching everywhere!!!

  37. October 11, 2013

    […] bookings! I’m going to have to get myself into gear ready for the middle of November // this great post on when to wear knee high boots and when to go for ankle boots instead // blood red nails // […]

  38. October 14, 2013

    […] – This is only something I really started to consider after reading this fantastic post all about when to wear knee high boots and when to wear ankle boots. Knee high boots, when worn with […]

  39. October 15, 2013
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  40. October 21, 2013
    Ru says

    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

  41. October 21, 2013
    Jules says

    Hi there,

    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!

  42. November 2, 2013
    Nancy Wance says

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  43. November 6, 2013
    Sue says

    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!!!!!

  44. November 8, 2013
    Natalie says

    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!

  45. November 11, 2013
    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!

    Thank you!!

  46. November 12, 2013
    katie says

    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.. :(

  47. November 21, 2013
    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!

  48. November 25, 2013
    Jenny says

    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. :/

  49. December 2, 2013
    Magda says

    Its like you read my mind! You apppear to know so mch about this, like you wrote the book in iit or something.
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  50. December 5, 2013
    Mary says

    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. :-(

  51. December 14, 2013
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  53. December 19, 2013

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  54. December 30, 2013
    Elizabeth Burke says

    I love this post and I’ve referred to it for many outfits! I would love to know where your booties are from or what brand they are– so cute!!

  55. January 2, 2014
    KIMINA says

    What kind of riding boots are those?

  56. January 21, 2014
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  57. February 4, 2014
    jo says

    does anyone know where i can find these ankle booties!!!!?

  58. February 7, 2014
    Jessy says

    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…..:);)

  59. February 12, 2014
    Donald says

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  60. March 5, 2014

    How do you feel about ankle boots with leggings???

  61. March 19, 2014
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  62. March 21, 2014
    Lizz says

    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??

  63. March 21, 2014

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  64. March 24, 2014
    Middle Cyclone says

    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.

  65. April 22, 2014
    Kayla says

    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! :)

  66. May 1, 2014

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  67. May 3, 2014
  68. June 14, 2014
    EricaD says

    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.

    Love, 30 something who has been a professional stylist, has given fashion and style advice to hundreds of thousands of people, and has worked with many people to build their wardrobes and teach them how to dress.

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  70. July 29, 2014
    Julia says

    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.

  71. August 27, 2014
    Catherine says

    I have been looking for the perfect knee high boots, and those are beautiful! Could you tell me what boots they are?

  72. January 15, 2015
  73. February 20, 2015
    Chelsea says

    Ankle boots don’t always look as good as you suggest. I wouldn’t wear booties with:

    – light jeans
    – shorts
    – 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!

  74. September 2, 2015
    a man who knows better says

    You are wrong, the knee highs win every time

    1. November 22, 2016
      Andrea says

      True! Except of the boyfriend jeans

  75. October 4, 2015
    Samantha says

    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 ?

  76. October 15, 2015
    Susan says

    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!

  77. October 21, 2015
    Collin says

    Great post! Very helpful comments about each look. Had to pin for reference :)

  78. November 6, 2015
    Amanda says

    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’.

  79. November 9, 2015
    rudey says

    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.

  80. December 11, 2015
    Bessie says

    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.

  81. December 14, 2015
    Lisa says


  82. December 29, 2015
    Mary says

    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!

  83. January 6, 2016
    Batgirl says

    I really did agree with some of the printed skinny jeans would look better with knee-high boots and light skinny jeans knee-high boots!

  84. January 6, 2016
    Batgirl says

    I really did agree with some of the 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.

  85. January 6, 2016
  86. February 16, 2016

    […] – This is only something I really started to consider after reading this fantastic post all about when to wear knee high boots and when to wear ankle boots. Knee high boots, when worn with […]

  87. February 27, 2016
    Maria says

    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.

  88. April 6, 2016
    April says

    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. :)

    1. May 21, 2016
      jay says

      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

  89. May 30, 2016
    Raina says

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  90. June 1, 2016

    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.

  91. November 13, 2016

    […] When To Wear Ankle vs. Knee-High Boots […]

  92. November 22, 2016
    Andrea says

    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.

  93. December 12, 2016
    Ariana says

    I don’t have ankle or knee high boots.I mostly have over the knee boots.because I think they are better.

  94. February 16, 2017

    […] When To Wear Ankle vs. Knee-High Boots […]

  95. October 30, 2017
    Michelle says

    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!

  96. November 8, 2017
    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.

  97. November 13, 2017
    Sasha says

    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!

  98. January 13, 2018
    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.


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