Over the Knee Boots Over 40 ! Yes, You Can!

Over the knee boots over 40? Yes you can!

Over the knee boots over 40? Yes, you can.

A good pair of boots can change your life. I remember being a little girl in the 70’s and seeing one of my aunts wearing a pair of white go-go boots. I thought she was the coolest thing I’d ever laid my eyes on! Now- I saw my aunt all the time, but those boots transformed her. She looked so happy and radiant and was just oozing confidence. And therein began my love affair with the look of a smashing pair of boots.

If you follow trends you’ll know that the over the knee boot trend has been around for several years and is showing zero signs of slowing down anytime soon. And if you like the trend, you most definitely can wear it! Over 40 or not, you CAN wear over the knee boots.

When I began shopping for a pair of over the knee boots, I just wasn’t sure how much wear I’d get out of them. Well, I’m already on the hunt for another pair and for as much as I’ve worn them, I am now ready to invest in some pricier ones. These will be a favorite for upcoming holiday parties!

Styling Over The Knee Boots

I wear them most often with jeans. The lighter the denim, the more the boots will stand out. The darker the denim, the more lengthening of the legs. I prefer a medium-dark wash denim. (If you wear black denim with black suede over the knee boots- the boots tend to get lost, so keep that in mind). I use the boots themselves as the standout piece in my outfits and tend to keep the rest of my look more minimal, but if your style is bolder than mine, then, by all means, add a statement coat on top- a faux leopard print coat would be amazing! Here, I’ve paired it with a black v-neck sweater, a Blank NYC moto jacket and a leopard print scarf that my youngest son got me in South Africa, (I adore the authentic leopard print!).

over the knee boots over 40

If you are heavier through the hips and legs, consider pairing these with a long cardigan or long coat over the top, to keep a leaner looking line.

If you are more petite, just think about keeping that long line. If you have black boots, wear dark (not black, because you still want to SEE the boots) jeans and keep everything else black to achieve a look that doesn’t chop you up. (I am 5’5 and this is how I usually wear them.) Or again, pair them with a long cardigan to keep that more elongated look.

If you are tall, over the knee boots will look amazing no matter how you wear them. They will accentuate your height and it may be a little harder to find a shaft that comes up as far as you want it to, so be sure to measure.

over the knee boots over 40

These are the perfect winter boots and will keep you so much warmer when you’re headed out at night. I really fell in love with the over the knee boots on our recent trip to Winter Park, Colorado. The sturdy heel makes them super comfortable as well. Fashion AND Function? I’ll take it.

over the knee boots over 40

Shopping For Over The Knee Boots

If you are ready to make a real investment, the Stuart Weitzmans are hands down the way to go. They make your legs look a mile long and are just gorgeous. They can sometimes be found discounted at places like Last call by Neiman Marcus.

There are also some great dupes for the Stuart Weitzmans:

Or go for a bargain pair at first to see if you really like them.

If you are shopping online read reviews to see how well the boots stay up and how they fit different calf sizes. If you are shopping in the store really walk in them a bit to be sure they will stay up on your leg and that they, of course, feel comfortable.

If you want to elevate your look this winter, I highly recommend getting yourself a great pair over the knee boots. They are going to be a trend for quite a while, so if you love the look- scoop up a pair! Do you already have some? Do you love them? Have you found a favorite brand? I’d love to know what you think while I search for my next pair!

Don’t forget to follow me on Instagram, where I tend to constantly over-share on my Stories! 😀

You may also enjoy reading some of my favorite fashion bloggers here.

Or about how I make extra side cash for spa/ salon visits here.

And you might need to reminded to take good care of YOU this holiday!

Pin this post here!

over the knee boots over 40!

Melissa is an unrepentant shoe hoarder who is obsessed with travel, wine, good food and her family. (Not necessarily in that order!)

Find me on: Web | Instagram | Facebook


  1. Dolores Harmon Doxey
    November 29, 2018 / 7:45 pm

    Yes I use to love my boots. I also wore them folded down below the knee. I use to like to where them with my blue jean skirt and a sweater top or a balarinia top. They were very comfortable and of course that was a time when skirts came a little above the knee. Looking at the price of them today, they have really gone up in price and hopefully they won’t wear out for a long time. Mine probably lasted me for at least 5 years before I wore them out. They really kept my feet and legs warm.

    • melissa
      December 4, 2018 / 8:16 am

      You were definitely quite the fashion plate! The ones today do last a long time and I love how comfy and warm they are too! Thanks so much for reading and commenting!
      ~Melissa xx

      • Reese
        December 19, 2018 / 1:16 pm

        Melissa, when you look like you do, you can wear OTK boots! You have the body of Wonder Woman!

  2. November 30, 2018 / 1:05 am

    Hell yeah! I am over 50 and have three pair!

    • melissa
      December 4, 2018 / 8:17 am

      Ha! ha! Nancy! And you really know how to rock them too! I love it.
      ~Melissa xx

  3. November 30, 2018 / 6:12 am

    I have a black pair, VERY similar to yours, and I have an olive green pair. I love them both, and they’re surprisingly warm. You’ve reminded me that I need to get them out and start wearing them ASAP! I love yours with jeans and your biker jacket (and OF COURSE the leopard scarf). Gorgeous, Melissa! xx

    • melissa
      December 4, 2018 / 8:19 am

      Thank you Lisa! I would love to see how you style yours- I know you’re not a denim gal. Do you wear them withy skirts mostly? And I NEVER see the olive green color- I bet they are beautiful! Do post on IG when you bust them out! Can’t wait to see.
      ~Melissa xx

  4. November 30, 2018 / 7:50 am

    You are singing my song! I adore OTK boots and have been on the band wagon from day one. I have at least four pairs and then a couple that go just to the knee which I can’t stop wearing this season. I got to wear the old go go boots in high school as a member of the dance team and thought I was the cat’s meow! By today’s standards you wouldn’t call us a dance team though. Ha ha! You look so amazing! I love this whole look and now think I will wear a pair of OTK today! Thanks for the inspiration!

    • melissa
      December 4, 2018 / 8:21 am

      Thank you Cheryl! I have a few “just to the knee” boots that I have on repeat every winter. I seriously just can’t get enough. I bet you were super cute in those go-go boots!
      ~Melissa xx

  5. December 10, 2018 / 1:05 pm

    Those boots are gorgeous!!! And they look great with the whole outfit. I have over the knee boots and I love wearing them, even though I’m not “forever 21” anymore – haha. I like to call that store “forever 41” because sometimes my friends and I still shop there. xo

    • melissa
      December 14, 2018 / 9:43 am

      Not sure how I missed this- ………thank you! I love your name for “Forever 21”!! Ha! Ha! Much more accurate I’d say. Thanks so much for reading and commenting!

  6. Jodie
    December 12, 2018 / 11:02 am

    Yep…I love them and plan to add more to my collection. I mean really….my mom is 80 and has 3 pair. So it’s definitely for any age woman!!

    • melissa
      December 12, 2018 / 1:03 pm

      Oh Jodie I can’t tell you how much I LOVE that your 80 year old mom has three pair of over the knee boots!Just love all three of you ladies! Thanks so much for reading and commenting!
      ~Melissa xx

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