1. 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 :)

    Reply
  2. Shannon says

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

    Shannon
    http://GBOfashion.com

    Reply
  3. Alyssa says

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

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

    Reply
  5. 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 ;)

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

    Reply
  7. 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.
    Thanks

    Reply
  8. 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?

    Reply
  9. 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

    Reply
  10. 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!

    Reply
  11. 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).

    Reply
  12. [...] boots or knee highs? Check out this post to know which to wear [...]

  13. Nicole Maher says

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

    Reply
  14. Taylor says

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

    Reply
  15. Yasmin says

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

    Reply
  16. tight&skinny says

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

    Reply
    1. tight&skinny says

      [additional]
      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.

      Reply
  17. LOVE this post!!

    Reply
  18. 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 – http://champagnespit.com/fashion-advice/what-to-wear-with-knee-high-boots

    Reply
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  20. 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

    Reply
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  23. 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.

    Reply
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  26. Jennifer says

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

    Reply
  27. 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!

    Reply
  28. Helen says

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

    Reply
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  31. 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!!

    Reply
  32. 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?

    Reply
  33. Joanna says

    This was very helpful! Thank you

    Reply
  34. 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

    Reply
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  36. Lisa says

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

    Reply
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  40. 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
    Thx

    Reply
  41. 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!
    Jules

    Reply
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  43. 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!!!!!

    Reply
  44. 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!

    Reply
  45. 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!!
    Charity

    Reply
  46. 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.. :(

    Reply
  47. 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!

    Reply
  48. 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. :/

    Reply
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  50. 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. :-(

    Reply
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  54. 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!!

    Reply
  55. KIMINA says

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  57. jo says

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

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  58. 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…..:);)

    Reply
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  60. How do you feel about ankle boots with leggings???

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  62. 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??

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  64. 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.

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  65. 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! :)

    Reply

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