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How to Wear Boots of Varying Heights


Cute boots

A hot pair of boots (or three!) is a definite college girl essential. Though especially practical in winter because of the cool temperatures, boots are great year-round because they’re low-maintenance and cute, and can be worn in every season.

Whether you prefer short boots, medium height, or above-the-knee styles, there is a perfect pair of boots out there for you! This guide will help you choose a pair and learn how to wear them.

Short: Booties & Ankle Boots

Booties and ankle boots were huge last year, and the trend doesn’t show any signs of cooling down. Ankle boots, like their name would suggest, sit at or slightly above ankle-height. Though high-heeled ankle booties have been seen on celebrities and fashionistas alike, flat ankle boots, especially with embellishment have become increasingly popular as well.

Hot Picks

Cute Ankle Boots

Product Information: Dolce Vita Flash Bootie, Qupid Muse16 Ankle Boots, Leopard Suedette Ankle Boots, Dorothy Perkins. Minnetonka Tramper Ankle Hi Moccasin Boots, Net-a-Porter.

Tips for Wearing Ankle Boots

  • Choose your heel height wisely. For most of us, flat ankle boots will be a more practical option than their high-heeled counterparts. For fancier occasions, ultra high-heeled platform booties are a stylish, showstopping option.
  • Watch the proportions. Because they are so small, ankle boots can look awkward with fuller silhouettes up top (think boyfriend jeans or a full skirt), but are a great option if you’re trying to showcase your legs. Show off those legs by paring ankle boots with leggings, skinny jeans, or short skirts and dresses. They also look amazing when worn with tights.
  • Notice the rise. As I mentioned earlier, ankle boots can hit at, below, or slightly above your ankle. Though all of these rises look cute with pants or leggings, getting the rise-to-leg ratio right with skirts and dresses can be a little confusing. It doesn’t have to be! For the most part, the higher the rise of the boots, the shorter your skirt or dress should be. Boots with a higher rise paired with a longer skirt shortens the look of your legs. Worried about revealing too much in a micro-mini? Add a cute pair of tights to your look!

Outfit Inspiration

How to wear ankle boots

Product Information: 7 For All Mankind Roxanne Skinny Jeans, Piperlime. T By Alexander Wang Classic Mini Pocket Tank, La Carçonne. Juicy Couture Tara Moccasins, Ssense. The Boyfriend Blazer, Fred Flare. Marc by Marc Jacobs Postal Big Percy Bag, Zappos.

Medium: Mid-Calf & Knee-High Boots

Medium rise (mid-calf and knee-high) boots are likely what you think of when you hear the word “boot.” From casual cowboy styles to dressy heels to slouchy motorcycle styles, medium rise boots are always in style. Not simply reserved for crunching leaves or navigating slushy streets, classic rise boots edge up summer staples like sundresses and denim cut-offs. The classics never go out of style!

Hot Picks

Cute, classic boots

Product Information: Paris Hilton Petit Boot, Steven by Steve Madden Intyce Boots, BDG Leather Riding Boot, Urban Outfitters. Carson Pull On Western Boots, Frye.

Tips for Wearing Classic Rise Boots

  • Know your occasion. Classic-rise boots come in a ton of different varieties, each of which can put a different spin on an outfit. In general, slouchy and cowboy styles are more casual, while luxurious leather or suede boots, heeled or flat, provide a more formal option.
  • Tuck them in or leave them out. Skinny jeans tucked into mid-rise boots are a perennial fall staple. Another option, however, is to wear your boots under your favorite pair of boot-cut jeans. The result is totally chic–just a peek of the heel and toe of your boots!
  • Consider your calves. Classic-rise boots can hit mid-calf or just below the knee. Either way, it’s important that the boot doesn’t gape too much–it should fit snugly but comfortably around your leg. If you have athletic or curvy legs, stretchy, slouchy, or zippered styles are a great bet.

Outfit Inspiration

How to wear classic mid-rise boots

Product Information: Statement Floral Printed Seed Bead Bracelet, Asos. Braided Chains Headband, Forever 21. True Religion Joey in Lonestar Jeans, Zappos. Cami Yellow Floral Tank, Abercrombie & Fitch. Pompa Cowboy Boots, Aldo.

High: Thigh-High & Over-the-Knee

Over-the-knee boots are this winter’s hottest trend in shoes. And, as CF author Collen proved in her article about her favorite over-the-knee boots, they’re totally wearable no matter your height. Thigh-high boots are fashion-forward, and will definitely add some edge to your outfit. They can also look downright chic when worn with a dress or cigarette pants. Because this style of boot provides some extra coverage and warmth, now is the perfect time to try out a pair!

Hot Picks

Cute over the knee boots

Product Information: Charlie My Love Over the Knee Easy Rider Buckle Boots, Restricted Vamp Boots, Piperlime. Faith Meryl Over The Knee Flat Boots, Asos. Nicole Right Now Copper Boots, Lori’s Shoes.

Tips for Wearing Thigh-High and Over-the-Knee Boots

  • Be fearless! Though tall boots can seem tough to wear, they’re incredibly easy to pull off and can really add sophistication to an otherwise basic outfit. If you would normally wear classic-rise boots with an outfit, then thigh highs would likely look equally awesome. If you’re wearing something short, make sure to add tights or leggings since over-the-knee boots are already super sexy on their own.
  • Try convertibles. As Colleen mentioned in her article, some over-the-knee boots are convertible–they can be worn folded down below the knee, or flipped up above it. If you’re unsure about this trend, a convertible boot is an excellent way to try it out without committing. Convertible boots also make it easier to bend your knees when you sit or walk since they’re not stiff. What could be better than comfort and two looks in one?!
  • Keep it simple. Because these boots attract attention, it’s best to keep the rest of your outfit simple so your boots will really make a statement. My favorite over-the-knee boots are similarly uncomplicated–I like them without much embellishment or detailing since their rise alone makes a huge impact. If you like your boots embellished, it’s especially important to keep the rest of your look simple and go easy on the accessories.

Outfit Inspiration

How to wear over the knee boots

Product Information: Vanessa Bruno Jersey Trapeze Tank, The Outnet. J Brand 12″ Pencil Skinny Jeans, Piperlime. Aubrie Waist Belt, Forever 21. 3.1 Phillip Lim Floating Shrug Border, La Garçonne. Very Volatile Joust Boots, Piperlime.


What do you think? What is your favorite boot height? What is your favorite pair of boots? Does your height influence the types of boots you choose? Do you have any tips on how to wear boots? Let us know with your comments!

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Posted on on January 15, 2010 / Filed Under: Fashion Tips / Tags: , , , , , , ,

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40 Responses to “How to Wear Boots of Varying Heights”

  1. 1
    January 15th, 2010 at 1:10 pm

    I always appreciate a fellow boot lover. I recently did a post about boots because I absolutely love them…they’re so versatile you really cant go wrong. My favorite type of boot is knee-high or over-the-knee because I think they’re the most flattering.

    Ankle boots are fun too. They have really emerged in the past few years and there are even different heights of ankle boots too. My favorite ankle boots are by Rosegold. They’re called Studded Fold-Over Ankle Boots in black (see ) and they are super fab!

    Great post! I <3 boots!

  2. 2
    January 15th, 2010 at 1:13 pm

    Awesome post! Thanks so much! I finally know what to do with my ankle boots and mid-calf boots! A quick question about flat ankle boots or mid-calf boots. Can they be worn with shorts?

  3. 3
    January 15th, 2010 at 1:42 pm

    great post :)
    i have a guestion can u wear mid-calf boots with a skirt that hits right above the knee?

  4. 4
    January 15th, 2010 at 2:32 pm

    I’m so glad you guys are liking this post! I love boots, so it was really fun to write.

    Zamia–I think you can definitely wear flat boots with shorts! It’s a totally cute, summery staple, but I’ve also seen girls look incredibly stylish wearing shorts, tights, flat mid-calf boots and a cardigan. I’m sure it would look equally cute with ankle boots, too! It all depends on your personal style, but if you’re up for it, go for it!

    Avory–I think you can! Because your boots are mid-range and your skirt is on the shorter side, you likely wouldn’t be ‘cutting off’ the look of your leg too much. I think mid-calf boots with skirts can look super feminine and bohemian.

  5. 5
    January 15th, 2010 at 2:40 pm

    Awesome post! I’m a boot-aholic, so I love all heights :)
    I am wondering however, my upper legs are rather ‘voluptuous’, would you recommend wearing overknee boots?

  6. 6
    January 15th, 2010 at 3:30 pm

    This article is great! I’ve been searching for the perfect pair of boots for awhile and will definitely be checking some of these out =)

  7. 7
    January 15th, 2010 at 3:40 pm

    This is a great post! However, remember that most college girls can’t afford designer jeans. I like College Fashion because the posts feature reasonably-priced clothing that can be found anywhere, that everyone can afford! I would just mix it up a bit in the future, rather than only featuring jeans from J Brand, True Religion, etc. Thanks!

  8. 8
    January 15th, 2010 at 4:27 pm

    I have to disagree about the boots with shorts…I don’t think it works at all. They look fine with skirts, but with shorts they look a little hooker-ish and silly. Just my humble opinion!

  9. 9
    January 15th, 2010 at 5:24 pm

    Thanks for the post!

    How would you recommend finding a good ankle boot for us shorter girls? I hear that ankle boots can cut you off and make you look even shorter…

  10. 10
    January 15th, 2010 at 5:46 pm

    I love boots- the majority of my vast shoe collection are boots.
    This post has give me the perfect outfit for 2moz so thanks!
    Also I agree with you on the shorts boots combo. In autumn/winter I often rock the tights boots shorts combo and get nothing but compliments! Ankle boots or calf boots

  11. 11
    January 15th, 2010 at 8:38 pm

    I just found these beautiful chocolate-brown (dark brown), knee-high, fake-leather riding boots , but I don’t know how to match them. What jacket or coat colors are okay? Can dark brown boots go with a black coat? A grey coat? A navy coat?

  12. 12
    January 15th, 2010 at 8:58 pm

    whats up with all these clothing outfits with expensive stuff? like marc jacobs, 3.1 phillip lim?

    umm, I thought this was college fashion?

  13. 13
    January 15th, 2010 at 9:14 pm

    Elena–Personally, I’m 5’8″ so I’m not exactly sure what to look for in a specific pair of boots if you’re on the shorter side..That being said, I think what’s most important is what you wear your ankle boots with. Anything monochromatic is going to give you a longer, more streamlined look, as would wearing your boots with pants. I wish I had more advice! Are there any other shorties out there with tips??

    Amy & Anon–the outfits I put together are just for some fashion inspiration, as I noted! Just some ideas on what to wear with your boots. If you don’t want to buy spend a lot, don’t! That’s totally your prerogative. I’m admittedly a designer jeans junkie, so that tends to come out in the outfits I put together! I’ll definitely try to include more reasonably priced jeans in the mix in the future, though!

    Charlotte–Those sound adorable! Brown is a pretty universal neutral, and would look great with the coat colors you mentioned– navy, grey, or even a bright pop of color like red or purple– if you’re game!

  14. 14
    January 15th, 2010 at 9:50 pm

    all the outfits r so pretty!! i love boots

  15. 15
    January 16th, 2010 at 12:27 am

    I’d LOVE to try over the knee boots, but since I’m a dancer, (plus I’m curvier than most girls, which is a double wham) most boots I try on can’t even fit my thighs. ): Any suggestions on getting an awesome pair of boots that can actually fit my legs? Thanks! (:

  16. 16
    January 16th, 2010 at 2:07 am

    Can you do a post about if it’s okay to break the rule (and how to do it) when it comes to wearing both brown and black?

  17. 17
    January 16th, 2010 at 2:32 am

    love the post
    but i always pair boots with skinnys for me
    the over the knee boots trend is my fav

  18. 18
    January 16th, 2010 at 4:07 am

    My favorite boot height is ankle boots. My favorite pair of boots is a pair of ankle boots with a heel that are gray, suede, and fabulous :) My height doesn’t really influence the type of boots I choose to wear because I’m 5’4 so I’m pretty much average height so I can kind of get away with any height. I would wear my boots with a plain white hanes tank top, regular wash skinny jeans, and a huge white bag.

  19. 19
    January 16th, 2010 at 10:25 am

    I love boots, so this post is perfect. My favorite part about fall is being able to pull on my boots again.

    Do you happen to know of any brands that make boots for skinny calves? I’m looking for mid-calf boots with flat or low heel, preferably black. I’ve been cursed with twig legs no matter what I do – my calves are about 12″ around, and I can’t find boots that fit since most seem to have at least a 15″ circumference and leave wide, hideous gaps. I’d prefer something under $200, but at this point, anything will do! Thanks!

  20. 20
    January 16th, 2010 at 1:00 pm

    great post!! boots are my winter wardrobe staple!!
    I have everything from bright pink wellies to Uggs and i have 5 pairs of black boots!!
    I think ankle boots are definitely my favourites though- especially heeled shoe-boots!!


  21. 21
    January 16th, 2010 at 1:37 pm

    Short girls! Be VERY careful about OTK boots. at 5’0”, they completely take over my legs and look just wrong. A lot of girls that are just a few inches taller can pull them off, though. I usually go for a boot with a heel. Being short my whole life, I’ve gotten used to walking in them!

  22. 22
    January 17th, 2010 at 2:30 am

    Hey i liked this article. but i agree with the previous statement about the super expensive articles of clothing — i really liked that shrug from la garconne. $395? Why even post that on here? its a college student site…

  23. 23
    January 18th, 2010 at 6:17 pm

    ok i love the website about boots im5’10 so i know i can rock any pair of boots lol

  24. 24
    January 18th, 2010 at 9:51 pm

    Great guide and SO helpful! wonderful tips, it was nice to just read and connect with what i have in my wardrobe :)

  25. 25
    January 20th, 2010 at 2:35 pm

    Love the outfit inspiration for the over the knee boots!

  26. 26
    August 25th, 2010 at 6:12 pm

    Hi im 5’1″ and bought the cutest brown heeled midcalf boots and wondering how to wear them without looking weird. They gap alot at my calf when ive tryed them with short skirts or dresses and im wondering if thats just how they’re supose to fit or if they’d look better with jeggings or???

  27. 27
    September 28th, 2010 at 1:25 pm

    To Mimi:
    You might want to check this out, it’s cheap but comfortable and they fit comfortably on me. Just copy and paste this link…

  28. 28
    October 8th, 2010 at 10:51 am

    Ive just got some gorgeous fawn coloured heeled ankle shoe boots, but im struggling to get them to go with anything. Helpppppp! :)

  29. 29
    November 27th, 2010 at 9:27 am

    I am a 67 year old women. I am over weight, mostly my stomach but my legs and ankles still look good. I am 5′ 3″. I am on a fixed income but like to look as good as I can, with Walmart, Target, Catos prices. I want to wear boots. I wear pants 99% of the time.

  30. 30
    December 3rd, 2010 at 7:01 pm

    “it’s important that the boot doesn’t gape too much–it should fit snugly but comfortably around your leg.” I love boots, but cannot find any that fit around the calf properly. I have skinny calves! While I keep seeing “wide calf” boots I’ve never seen narrow calf boots. Do you know of a company that makes them for a reasonable price?

  31. 31
    April 26th, 2011 at 4:18 pm

    I absolutely love that look! Totally my style, though I don’t have a pair of over-the-knees yet. Surprising, since I love boots!

  32. 32
    June 13th, 2011 at 9:58 pm

    Nice post! I absolutely adore the very first pair of booties!
    @Laura Great question! I have the exact same problem! It’s so hard to find a pair of boots that will fit my skinny calves.

  33. 33
    June 28th, 2011 at 4:31 am

    Skinny-legged friends, do not despair: take your boots to a cobbler- he/she can take them in for you! I had a pair of zippered riding boots taken in. Leather was removed along the zipper, then the zipper was sewn back in. They fit great – no gaps around my calves.

  34. 34
    July 27th, 2011 at 1:54 pm

    HI I love your post. I love boots and do wear them a lot even when its hot outside. I especially love to wear shorts with flat boots I think it looks pretty.

  35. 35
    September 2nd, 2011 at 10:53 am

    Thanks for such a great article, exactly what I was looking for. I recently have gotten into trying some different shoes and boots, since I really want to be able to wear heels (of which I’ve always had issues with comfort-wise). I found this fantastic stiletto ankle boot that I could walk in easily, my only issue with buying them was “whatever will I wear this with?”. I’d hate to have bought it to found out it looks terrible with everything I wear, lucky, I know now it goes right along with skinny jeans I often wear and my leggings and skirts! Fantastic! Thanks again! I’ll be getting some new boots today now! :D I might even check out some over the knee ones now as well… Soon I’ll be a shoe-a-holic.

  36. 36
    November 25th, 2011 at 9:54 pm

    ive been looking for a brown pair of riding boot for under $30 but ive had no luck. do you know where i can find some?

  37. 37
    April 12th, 2012 at 2:08 pm

    Hey girls, I found the tip about taking boots to a cobbler for skinny calf girls, I was wondering if you would know off hand if I could have cowgirl boots taken in by a cobbler? My calves are like freaking sticks, seriously.

  38. 38
    August 12th, 2012 at 3:35 am

    Would over the knee boots look good with a plain white t and a scarf?

  39. 39
    September 14th, 2013 at 10:41 pm

    Nice article..HELP! I’m 5’0″ with wide calves….. I want some boots that I can wear with skirts and skinny jean/jeggings. Having trouble finding a good height of boot at is flattering considering my calves and height. Send suggestions please!

  40. 40
    November 27th, 2014 at 2:58 am

    Hi, interesting read. Can you wear boots to a company annual party? Is that appropriate etiquette? Not with a pair of jeans but with a nice dressy skirt??

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