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


Over the knee boots aren’t only for jeans! You can easily work them with a dress. I like to keep it all one color and add some sheer tights. I keep the space between the hemline and the top of the boot to about 2 inches to avoid looking like I’ve raided a teenagers closet. 😉 The small flash of hosiery covered skin between the hemline and the top of the boots is sexy but doesn’t come close to crossing over my “trashy” line. The important thing is that you feel comfortable and not self-conscious. No one wants to spend an evening feeling self-conscious all night!

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. Bloomingdales has them right now and they can sometimes be found discounted at places like Last call by Neiman Marcus.


There are some good dupes of 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!

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