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.
Shorts:
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 look can feel a tad slutty, for lack of a better word, so I vote ankle boots. Plus, the proportions cut your legs off in 2 different spots, again making you look shorter.
Midi Skirts:
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.
Mini Skirts:
For the most part, straight mini skirts or dresses go with both ankle and tall boots. Of course, you want to consider again if the look is airing on the slutty side. For example, it’s better to pair the knee-high boots with a tight skirt/dress that covers more on top. 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
Shannon
http://GBOfashion.com
Love this! I actually have almost identical boots as both of these, and I often style them the same ways. Great post!
Yet another awesome post! I love the different comparisons you offer! Definitely an occasion for ankle boots vs. knee!
xo,
nancy
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 ;)
Love it! Ankle boots are on my shopping list, but I always wondered — how versatile would they be?
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
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?
Try ones with a lower heel. I’ve heard these ones by Sam Edelma. These Steve Maddens are a great option too!
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
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).
[...] boots or knee highs? Check out this post to know which to wear [...]
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?
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?
Cheers.
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*
I think white skinny jean is the best pairing with knee boots, as you see those horse rider you will know.
[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.
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