Over The Knee Boots Primer!

Hey everyone! Happy Friday! I’m wearing my new Over The Knee (OTK) boots I promised I’d show you on Wednesday. I took the leap because these were a really low cost way to give this style a try. These are an exciting addition for me because they’re very different from what I’m used to wearing and I enjoy trying to style something completely new!

Over 40 Fashion for Plus Size Women | www.whenthegirlsrule.com

I had my daughter take these pictures as I was headed out to the mall because I thought I looked so cute! I will say though I noticed I got two side-eye glances from women my age while at the mall and I think it was because of the boots. Now, it could be that they were just thinking how cute I looked or perhaps looking to see how I styled them but didn’t want to stare. I’m not sure, because that hasn’t happened (or I haven’t noticed) in a long time. But, I did what I always do when I’m in that situation: I held my chin high and said to myself “You are one foxy lady” and continued my shopping.

Over 40 Fashion for Plus Size Women | www.whenthegirlsrule.com

Now, these boots are different from the ones I wore on Wednesday. Those burgundy boots came to just over my knee cap and these boots are higher. Because the OTK boots are associated with younger women (or Julia Roberts from Pretty Woman), I thought I’d share a couple of strategies to keep you from looking like you’re trying to look like a teenager (or a hooker!) and thanks to Jodie from J Touch of Style for showing that women of any age can wear these boots!

So, first off you can try them with a low heel or no heel. This makes you look more serious and industrious (and makes me feel like Robin Hood)!

Try the suede rather than the shiny leather. The shiny leather is more attention grabbing.

Blend the color of the boot with the color of the pants. There will be less contrast at the top of the boots and it won’t draw the eye.

Wear with a skirt or dress where the hem covers the top of the boot. This way you get the leg coverage (and warmth — they’re really warm!) while you start to feel more comfortable wearing them and realize that they’re not that big of a deal.

Over 40 Fashion for Plus Size Women | www.whenthegirlsrule.com

Now, let’s talk about fit. If you’re built like me or similar you probably have wide legs. One reason I was afraid of trying these boots was because I was afraid they would be tight in the thighs like most boots are tight in the calves. Actually there are more options to fit a wide thigh than there are to fit wide calves. Believe it!

Look for a style that is more open in the back of the boot behind the knee, like this pair and this pair.

Or, do our favorite sleuthing tactic and look to see if they look too big on the model like here and here.

Over 40 Fashion for Plus Size Women | www.whenthegirlsrule.com

And finally, I noticed that there seem to be three different ways to keep these boots from falling down.

One is they are really tight, almost like leather or suede tights, and they stay up by constriction. See this example and this example. That’s not really the look I’m going for plus they’re pretty impossible to wear over clothing so you’d have to have bare legs. Pass!

Then there is another style where a string at the top ties them up (see here and here for what I mean). I haven’t tried this and I know many women seem happy with them, I just imagine them constantly slipping down and the strings loosening and constantly having to pull them up and re-tie them. Not my thing.

Third option is what I’m wearing. The fabric over the knee is stiff and stays in place. In some options it’s because it’s stiff leather (like here) or stiff because it has some thin padding that keeps it rigid and upright, like mine. It could just be the fabric doubled over that makes it stiff but it seems like there is some sort of stiff padding under the fabric. Either way, they’re stiff enough to stay up and flexible enough that they don’t chafe my knee when I’m walking.

I’m finishing off this outfit with new jeans and this old sweater you’ve already seen before (here) and a pretty necklace. I also have a new purse that I bought to lighten up my black outfits without having to bring out the pumpkin!

Ok, whew! I didn’t realize this would be such a long post when I started writing it. I’m back in North Carolina enjoying the weather and my new house. Stay tuned on Instagram stories for more tours of the house including the room I’m calling My Blog Room! Have a wonderful weekend!

Thank you for your clicks on the links and your purchases from those links! I receive a small commission from your clicks and purchases and I put that all back into this blog!

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  1. You ARE one foxy lady! I’m sure those ladies were admiring you in your well-fitting over the knee boots!

    I do love an OTK boot. I’ve had a black pair for a few years but they’ve actually stretched out so much that they slip down all the time (not a problem I usually EVER have with my giant calves!). I really need to have them taken in, cuz other than that, they’re a good fit and look nice. But I *would* like another color. Maybe next year. I have other things on the “I need a ___” list that are much more of a priority for this fall/winter.

    I’m so pleased to hear you’re back in NC – is this for good now or do you still have to return to MI for something…? Gah, somehow I keep missing your InstaStories…I’ll have to check again for new house pictures!


    1. Hey Bettye! The insta stories only stay up for 24 hours so it’s easy to miss them. I’m not in NC for good yet. Still have that pesky house to sell in Michigan. Plus both my daughters and all my animals (well, now two cats are in NC after yesterday’s looooooong drive!) are still in Michigan. I’m going to be a nomad for awhile I think. Have a great weekend my dear!

  2. What a wonderful surprise for the shoutout Julia!!! Thanks tons!!
    And aren’t you just so enamored with these OTK boots??? I feel like my other boots are going to get dusty now!!
    I have both varieties (the tie and the structured one), and I find the tie ones work better over pants & leggings—they seem to stay up better than on my bare legs. But I know my mom has added elastic in some of her regular boots that don’t stay up, so I may try that in the future!!!
    And you do look fabulous in these boots. If someone was checking you out—it could be they just aren’t used to the look. Once we get women realizing how fabulous and warm this style is—I have a feeling it’ll be everywhere!!!
    Have a great weekend!!

    1. I was thinking of Nancy’s boots that have the tie and I know you didn’t mention that they kept falling down so I figured some must work better than others. I think I’ll be wearing them lots in Michigan but it’s 68 degrees now in NC b/c these boots are so much warmer than I thought they would be. Have a wonderful weekend my friend!

  3. Julia,those boots and pants lengthen your legs, well you know what I mean . That is a great combo. The ladies were thinking that is a great combo I am sure
    Have a good weekend.🌲🍁

  4. The fact that they are the same color as the jeans makes the proportion right. Otherwise, very tricky, especially on a short person. The asymetrical sweater and bag are perfect.

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