Unique Older Women Style: Outfits with Thigh High Boots

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Updated 10/21/2021

Unique Older Women Style: Outfits with Thigh High Boots

Outfits with thigh-high boots may not be on your radar. Even though many styles recycle over and over again, there are times that a “new” style comes into our lives. Not that the thigh-high boots are truly new, but I think for most of us, they weren’t made for the average Jane. And I know I’ve said this many times before, but I really think these boots are fabulous for all of us.

Quote of the day: “It is hard to fail, but it is worse never to have tried to succeed.” Theodore Roosevelt

In fact, I bought my first pair of over-the-knee boots 2 years ago and loved them so much that I wrote a post explaining why. Now if you live anyplace that experiences winter these could be considered essential. And I mean a real winter, where it’s cold and you are tired of freezing. Because really and truly they are warmer than your other boots.

If you think you’re too short, too old, or that your calves are too wide, then let me say that there are some for every different size among us. Just so you know, the three of us range from 5’0″ to 5’4″.

Outfits with thigh high boots

In addition to seeing these lovely boots on the 3 of us, I was also lucky to have another blogger join us. Meet Lydia from I am Chic on the Cheap. We were talking about how we thought that outfits with thigh-high boots were the best thing since sliced bread when it came to keeping warm in the winter when wearing our skirts and dresses. And so I asked her to join us for this series. I hope you’ll pop over to her blog and introduce yourself.

What Exactly are Thigh High Boots?

For our outfits with thigh-high boots, I’m incorporating all boots that extend above the knee. The definition can vary depending on your height and the length of the boot shaft.

What all of these examples are showcasing is that these boots come in a range of colors, styles, and heel heights. In fact, none of our heels are over 2 inches which makes them easy to wear all day.

Insider tip: After wearing a trying over a dozen different thigh-high boots, I do recommend ones that have structure to them. Many of the lesser expensive ones have a shaft that falls down easily. It’s hard to figure this out if you are ordering them online, so the best course of action is to know the return policy first.

Jodie’s Outfit: These over the knee boots are my most recent pair that I bought from DSW, using one of my reward coupons.

Funny because most of us would probably buy black ones first, but no…I had to be different. My first pair was burgundy with a taller heel, and my next pair was olive green that was flats. These versions of boots come in many varieties. This kind is what you might consider baby steps to wearing outfits with thigh-high boots. Because they really are JUST over the knee. So they won’t come up as far as my other pairs do.

This could be the perfect way to start off and see if you really like the trend. And just so you know, I haven’t met anyone who tried them that didn’t like them. Everyone has been like me and has been surprisingly happy with this footwear.

Women over 50 in outfits wearing thigh high boots. Summer dress transitioned to fall.

Since my boots are black, I went ahead and chose a black sweater also. Just last week we showcased our sweaters and booties as a matching pair. And I think this is my usual when getting dressed.

Because of the black pieces, I chose my black choker and earrings. These earrings are the silicone ones that all 3 of us styled earlier this summer. It’s always so nice to wear these earrings because they are incredibly lightweight, and I forget I have them on. I included the discount code below my photos if you’re interested.

Over the knee boots for any occasion

My other fun accessory is this purse.

I’m not usually one to shop at the airport; however, when we were visiting Vegas last Christmas, my mom found this purse. And as a fashion blogger, how could I pass it up?

Over the knee boots for petite women

And you may not think about wearing a white floral dress once the fall season arrives. But in my defense, I had just purchased this dress on a big clearance on a recent shopping trip. When I get a new item, I really like to wear it right away, so I thought I’d layer it and try to make it season-appropriate.

I also tried to style it with a little yin and yang. The dress is girly, so I added in the leather detailed cardigan and choker necklace to give some rock and roll vibe to it.

Women 50+ and over the knee boots

Dress: Banana Republic (here)~~Cardigan: Maurices (similar here)~~Boots: G by Guess (here)~~Necklace: (similar here)~~Earrings: Coruu use JOTS for 20% off (here)~~Purse: (similar here)

Nancy’s Outfit: I love that Nancy wanted to get another color of over the knee boots instead of just black.

She was worried about the calf being big enough with these boots, so we went over to DSW, to try them on. However, the store didn’t have the blue ones in stock, so we ended up ordering them online. Luckily, she was able to try on the same style in another color, so she knew they would be fine.

Casual outfits with thigh high boots for women over 60. Short skirt and tall boots

For Nancy’s accessories, she chose her blue necklace and earring set. Do any of you like the idea of the necklace and earrings that match each other?

I know it can certainly make choosing the pieces easier when getting dressed. Therefore I thought I’d find a couple more sets for you. If you were looking for a lighter color then this would be nice. Or there’s a southwestern theme set available. Of course, a gold set would work for almost any outfit.

Over the knee boots in an outfit

This skirt is such has such a fun design on it.

Nancy is covering the top part of the skirt with her sweater, but you can see the whole thing when she wore it with her leggings. Nancy feels like the skirt is a tad too short to wear without tights and leggings, but now with these over-the-knee boots, it seems fine.

Over the knee boots with a short skirt

I should confess that I asked Nancy to buy these boots for the blog. I’m not sure she was super hip on the idea on her own.

In case you are vacillating on getting this particular set, she has noticed that they tend to creep down somewhat after wearing them for a while. Although the last time she wore them, she said she tightened the laces on the back much tighter, and they were better.

Insider tip: If you have skirts that seem a tad short, then the thigh-high boots are the perfect complement. You still see a sliver of the leg, but it is still very modest.

Boomer women wearing over the knee boots

Skirt: Desigual (similar here)~~Sweater: The Limited (similar here)~~Boots: Unisa (here)~~Necklace: (similar here)~~Earrings: (similar here)~~Sunglasses: (similar here)

Charlotte’s (70+) Outfit: My mom received her over the knee boots from our collaboration with Jambu earlier this year.

I had shown my mom a couple of pairs of over-the-knee boots when we were shopping earlier in the year. However, her rationale for not buying any was that she already had so many tall boots in her collection, she didn’t feel the need to get a pair of this variety.

But considering how often my mom loves to wear skirts and dresses, I theorize that this won’t be her only pair for long.

women over 70 wearing over the knee boots

My mom opted for a flower pin as her accessory of choice instead of a necklace. Would it surprise you if I told you that she had more than a dozen of these pins? Many of them she has made herself with leftover materials, but this one was actually purchased.

These accessories can certainly add some fun to your sweaters this winter. And if you aren’t willing to make your own, then this one or this one is quite lovely.

over the knee boots with a dressy outfit

Most of us don’t search for skirts that feel too short for us.

However, I know that all 3 of us happen to have a couple of these in our closets. And just like for Nancy, wearing these over-the-knee boots with them is a great way to make them work. And then with the addition of tights, you’ll be nice and toasty.

over the knee boots for warmth

I reviewed many of the points about these Jambu boots especially in the initial post where we styled them with casual outfits. The tread on the bottom is very impressive, so if you worry about slipping, then this would ease your mind.

Outfits with thigh high boots worn by older women

Skirt: Ric Rac Designs (similar here)~~Cardigan: Alfani (similar here belted or here not belted)~~Turtleneck: Lands End (similar here)~~Boots: Jambu c/o (here)~~Earrings: (similar here)~~Pin: (similar here)

I hope the 4 of us have shown how wearing outfits with thigh-high boots can be appropriate for women of any age.

Thanks to one and all of you for your support. It means more than you know!


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