9 Over-The-Knee Boots

These boots were made for walking...and getting complimented in.

Even though they’ve been the hot thing for a few seasons now, for whatever reason, I’ve been really hesitant to buy a pair of over-the-knee boots. I think I worried that because I’m on the petite side, they would look silly on me — which in hindsight, is totally nonsensical since I own and love several pairs of regular ‘tall’ boots!

Recently, after saving some gift cards and store credits from Shopbop, I was able to splurge on a pair of the famed Stuart Weitzman 5050 boots. Believe me, I didn’t take spending that kind of dough on a pair of boots lightly, but after reading tons of reviews and talking to a few friends who owned them, I was convinced that they’d be a great investment. And so far, so good — I’ve worn them a bunch of times since temps started cooling off here in New York, and not only are they super comfortable, but I absolutely LOVE the way they look. All my concerns about looking shorter in them were for naught; if anything, I feel like over-the-knee boots elongate the leg and have a slimming effect. The only funny part about them is watching me try to take them off — I still haven’t mastered the art of removing such a tall boot with anything that resembles grace!

But falling in love with over-the-knee boots has created a problem: now, I want them in every color and heel height! I recently came across these gorgeous Michael Kors over-the-knee boots and have been hemming and hawing over whether to get the black, dark brown, or camel color (or whether to just curb the addiction now, a “quit while I’m ahead approach”). Regardless — and especially compared to the 5050s and other brands — I thought the price was pretty good on these. All my over-the-knee boot obsessing has led to a bit of scouring the Internet on my part, so I figured I’d share a round up of 9 different over-the-knee boots for every budget! Which pair are your favorite? Have you invested in a pair of over-the-knee boots yet?



  1. 10.9.14
    Jessica said:

    Over the knee boots always look so sexy and understated. I’m not sure if I could wear them all day without getting tired of them, but they sure are fun!


  2. 10.9.14
    jillian said:

    yahh! for once i like the cheapest pair! great round up! xo jillian

  3. 10.9.14
    PJ said:

    So jealous of your pair of Stuart Weitzman’s! I’ve been drooling over the SW Highland style for monthsssss now :) I’m petite (and thin) — would love to see how a fellow petite styled them!


    • 10.9.14

      I can’t promise an outfit post (I’m the worst at them, truly), but essentially, I’ve been pairing ’em with black leggings, various neutral colored tops, and with this Free People jacket (in the camel color): http://bit.ly/10WDLQf. I think the length and slouchiness of the sweater jacket pairs really well with the sleek and kinda sexy boots! ;)

      Thanks so much for your comment! The SW’s were an investment for sure, the most I’ve ever spent on boots by far, but I can tell I’ll have them for years and years.

  4. 10.9.14

    I finally got the 5050s this year too, after pining away for them for what felt like forever! I really think they’re worth the investment…I mean, Michelle Obama has a pair, so that made me feel like I’ll probably be able to wear them for years to come!

    • 10.9.14

      You got them!!! How fun (I saw your post a while back!). I know you’ll treasure them too :)

  5. 10.9.14
    Tyshia said:

    I want those dolce vita boots! Love. I’m petite too but that isn’t stopping me one bit!

  6. 10.9.14

    I love the various options in this post, but these definitely aren’t for every budget. Happy Thursday :)

    • 10.9.14

      Hi hi! Thanks for your comment. I think in titling this post, I came from the angle of what’s on the lower end, the average, and the high end for this type of boot based on major and recognizable online retailers. In looking around, the most affordable options that I felt were still good quality, would hold up through multiple seasons, and represented the aesthetic I’d want to feature on the blog all started at around $100 — some a little lower, in the $80s, if there was a good deal or sale. Sometimes, when I do these types of posts, I can find better deals, but the product might only have one size in stock, which I don’t think is helpful for people who actually would like to order a pair, so I choose not to feature those. By far a large majority of over-the-knee boots offered by major retailers were in the $200 range, which is why I focused many of the options in this range (it seemed like that was about average for the market). Boots in general are definitely not the cheapest things ever, for sure.

      Regardless, I really appreciate your comment, especially the constructive way in which you left it, and definitely appreciate your frequent participation in the community here! Happy Thursday to you too!

  7. 10.9.14
    Zelena Sellman said:

    The cheapest pair on here is $99.00 and that’s a stretch. Unless Jesus comes in the box with the rest I wouldn’t buy. I’m not sure in which universe you live that has you thinking most people can afford,without being irresponsible on some other area of finances,to buy any of these shoes! I can pay a bill, buy a FEW new outfits, or stuff my deep freezer with that money. In the real world, people would laugh and keep moving. instead of wasting your money on things you can’t take with you when you leave here and go sew into something real. The excess you think is the norm IS NOT THE NORM. Get a reality check. Most of your readers look at your post like they window shop and keep strolling. Rethink how to reach your audience realistically. You don’t have to be poor to have common sense. Smh. Wasting money on stupid stuff when you could make a real impact on something that matters. Vanity ruins so many. I’m annoyed by this post obviously.

  8. 10.9.14
    Ujjaini said:

    These are such winter/fall must-haves! One for all


  9. 10.9.14

    I love the look of black over-the-knee boots, especially with leggings or tights for the cooler months. Once the season sets in, I honestly live in black suede boots. While I’ve had my eye on the Stuart Weitzmans, I found a similar pair last season I LOVE for around $200. I agree with your point above: I appreciate seeing quality options (across reasonable price points for the particular item/style) that are carried by reputable retailers – in the end, I would rather save for a quality item that will last me multiple seasons withstanding wear. (Especially when it comes to boots.) Thanks for this post!

  10. 10.9.14

    Hmmm okay, you just convinced me I need those Sam Edelman boots. LOVE!

  11. 10.10.14

    ahhh you read my mind!! I was just looking at different over the knee boots after a recent pair of black riding boots didn’t quite work out. Did any of your friends have the Lowlands? I’d love to know how they have held up in the winter (rain, snow, etc)… always a concern with suede, but I just love the look of the all suede over the knee boots.

    Thank you!


    anisa | whisk & heels

    • 10.10.14

      Hi Anisa! I only know of friends with 5050s, but a few people have ’em in suede and felt like they did fine however, I wouldn’t wear them in snow or anything like that — the wet snow could stain or ruin them.). I think Kat from With Love From Kat has a pair of the Lowlands though…perhaps tweet or email her and see what she thinks! I love the look of the all suede too, but I ended up going with regular leather 5050s because I felt like I’d be able to wear them throughout the winter and not worry so much, whereas suede ones would potentially be an ‘autumn only’ situation. Happy Friday :)

  12. 10.10.14
    Jen said:

    I’m loving over the knee boots as well! I had a pair of Kenneth Cole boots awhile back that were over the knee and I loved them. I’m saving up for the 5050 boots :)

    xo, Jen

  13. 10.14.14

    I have to admit, I’ve tried so many over-the-knee styles, and I now swear by the Stuart Weitzman’s – they are comfortable and beautiful (and crazy pricey … but totally worth it!)

  14. 10.24.14
    Jessica said:

    Thanks for this post on OTK boots! Love it. I rarely comment, but Zelena’s comment was terrible and upset me. I think you did a lovely job putting together this list. Quality boots are an investment!

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