Leave a Comment

Thank you so much for taking the time to comment! Your email will not be published or shared, but you will receive an automatic email if your comment has a reply.


  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 :)

  2. Shannon says

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


  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!

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

  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 ;)

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

  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.

  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?

  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

  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!

  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).

  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!!

  14. Taylor says

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

  15. Yasmin says

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

  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.

    1. 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. LOVE this post!!

  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

  19. Please let me know if you’re looking for a article author for your site. You have some really great posts and I feel I would be a good asset. If you ever want to take some of the load off, I’d really
    like to write some material for your blog in exchange for a link
    back to mine. Please send me an e-mail if interested. Thanks!

  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

  21. An impressive share! I’ve just forwarded this onto a friend who has been conducting a little homework on this. And he actually ordered me breakfast due to the fact that I stumbled upon it for him… lol. So allow me to reword this…. Thanks for the meal!! But yeah, thanx for spending time to discuss this topic here on your website.

  22. Hi to all, how is the whole thing, I think every one is getting more from this site, and your views are good designed for new visitors.

  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.

  24. I blog quite often and I seriously appreciate your information.
    This great article has truly peaked my interest.

    I will take a note of your blog and keep
    checking for new information about once per week.

    I opted in for your Feed as well.

  25. 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. Jennifer says

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

  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!

  28. Helen says

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

  29. I’m really enjoying the design and layout of your website.
    It’s a very easy on the eyes which makes it much more enjoyable for me to
    come here and visit more often. Did you hire out a developer to create your theme?
    Superb work!

  30. Latosha says

    This iss really interesting, You are a very skilled blogger.
    I have joined your rss feed and look forward to seeking more
    of your fantastic post. Also, I have shared your web site
    in my social networks!

  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!!

  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?

  33. Joanna says

    This was very helpful! Thank you

  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

  35. What’s up, this weekend is nice in support of me, as this time i am reading this fantastic educational article here at my home.

  36. Lisa says

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

  37. […] 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. […] – 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. Windy says

    Hey I know this is off topic but I was wondering if you knew of anny widges I
    could add to my blog tjat automatically tweet my newest twitter updates.
    I’ve been looking for a plug-in like this for quite
    some time and was hoping maybe you would have some experience with something like this.
    Please let me know if you run into anything. I truly enjoy reading your blog and I
    look forward to your new updates.

  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

  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!

  42. Nancy Wance says

    This would carry more weight if you used proper grammar, spelling, and correct words! There is a great difference between “too” and “to”. “Airing” does not mean “making a mistake,” but “erring” does.

  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!!!!!

  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!

  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!!

  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.. :(

  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!

  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. :/

  49. 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.
    I think thast yyou could do with a few pics tto drive tthe message home a bit,
    but nstead off that, this is excellent blog. A fantastic read.
    I will definitely be back.

  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. :-(

  51. Katie says

    Јust desire tto say your article is as amazing.
    The clearnesѕ in your post іs just spectaсular and i can assume you’re an
    expert on this subject. Well with your permission let me to grab your feеd to keep up to dаte with forthcoming pοst.
    Thanks a million and please carry оn the gratіfying work.

  52. Veгy quickjly his web page will bee famous among all blogging people, due tο it’ѕ fastidious articles

  53. Wow, this article is pleasant, my younger sister is analyzing these things, thus I am going to inform

  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!!

  55. KIMINA says

    What kind of riding boots are those?

  56. Valorie says

    If some ߋne ոeeds expert view regarding blogging after that i propose him/her to ρay a quick visit this blog, Keep up the pleasant job.

  57. jo says

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

  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…..:);)

  59. Donald says

    You want everyone to see where you started so your after pictures wil be more impressive.
    Therefore, do not hesitate to convey your ides to the

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

  61. Audrey says

    I am extremely impressed with your writing skills and
    also with the layout on your blog. Is this a paid theme
    or did you modify it yourself? Either way keep up the nice quality writing, it is rare to
    see a nice blog like this one these days.

  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??

  63. My spouse and I stumbled over here different web page and thought I might
    as well check things out. I like what I see so now i am following
    you. Look forward to checking out your web
    page for a second time.

  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.

  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! :)

  66. I just couldn’t go away your web site before suggesting that I
    actually enjoyed the usual info an individual provide for your guests?
    Is gonna be again ceaselessly in order to check up on new posts

  67. 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.

  68. Caryn says

    S unlicensed contractors Equities Realty, a U. The last thing we did
    everything you’re not alone and they are inside those walls and doors are.
    Besides, equipment failure, site damage etc. Spiral Duct FabricationSheet Metal
    FabricationScaffoldingPlumbingPipe and Heat TracingPipe InsulationPipe FabricationPanel Fabrication Millwright ServicesMechanical ConstructionInsulationHydronic HeatingHVAC ServicesHeating ServicesDuct Insulation Cladding ServicesAsbestos Removal Air
    ConditioningAir Distribution SystemsWhen you do?

  69. 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.

  70. Catherine says

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

  71. 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!

  72. a man who knows better says

    You are wrong, the knee highs win every time

  73. 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 😉

  74. 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!

  75. Collin says

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

  76. 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’.

  77. 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.

  78. 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.

  79. Lisa says


  80. 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!

  81. Batgirl says

    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!

  82. Batgirl says

    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.

  83. […] – 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 […]

  84. 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.

  85. 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. 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