Hat on woman over 50

Sure Fire Frump Fighting With Over-the-Knee Boots and Dresses

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You may think that over-the-knee boots and dresses are only for the younger crowd. Yet I believe that kind of thinking is what makes us get in that frumpy mindset to start with. So my goal has always been to try new trends and styles without judgment.

Without judgment can be one of the hardest things to do in this world. More about that is below.

Quote of the day: “There is nothing enlightened about shrinking so that other people won’t feel insecure around you.” Marianne Williamson

Have you ever seen a look or item on someone else and thought, she shouldn’t be wearing that? Maybe you deem it inappropriate for various reasons. Or maybe you use that term ‘she’s trying too hard.’
I used to be this way. In my mind, I felt like there was only 1 correct way to dress and I knew what it was.

These years of blogging have taught me many things. One of which is the definition of personal style. The name itself says it all. Personal style is personal. Personal meaning that it is meant for you and you alone.
Personal style is not wearing something because everyone else is wearing it, or because others around you might feel underdressed if you dress up.

Unfortunately, we all fall victim to this quote above, and many times it is SO ingrained in us we don’t even realize it.
What does this have to do with over-the-knee boots and dresses? Because I don’t see many older women wearing this combination of boots with their dresses and I don’t understand why.

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No frump with over-the-knee boots and dresses

Dress: Velvet Heart ~~ Top: Miacute c/o~~ Boots: Charlotte Russe ~~ Scarf: ~~ Earrings: Charming Charlie ~~ Purse: no label ~~Hat: Walrus ~~Glasses: Glasses Shop-code GSHOT35 for 35% off

Over-the-Knee Boots and Dresses

Dresses may not seem the obvious choice when it’s chilly outside, yet they can be just as warm as well as versatile. We think of dresses like one and done, yet you can layer over them and under them in many different ways (as I recently showed here).

While Charlotte showcased her somewhat shorter knee-high boots with her dress, the over-the-knee boots are even one step better. Why? Because obviously, they can keep you warmer because they cover more surface area.
Cathie wore a shorter cowboy boot with her dress.

Now if you’re like me, then when the over-the-knee boots first came on the market, you had visions of the character in the Pretty Woman movie. But just like any piece of clothing, there are so many modern variations that they don’t have to have that reputation.
For example, the pair I’m wearing has a flat heel and they don’t look sexy. They are modern, comfy, and fun. The part of this outfit that I consider sexy is that 4 inches of skin between the over-the-knee boots and dress.

Yet in all reality, you could wear these over-the-knee boots with a longer dress and not show any skin. To fight the frump factor in that example, I would recommend having contrasting colors for the dress and boots to show them off!

As I discussed in my mother’s post, a little bit of bare leg can seem very modern even though you might feel uncomfortable with it at first. In fact, one of my favorite outfits of my stepmom’s is this one with the same idea.

The reason this detail seems current is that you see these kinds of over-the-knee boots and dresses outfits on the younger girls. Yet that in no way means women our age can’t wear them. You don’t see older women wearing the combination much only because we get stuck in our style habits. And I bet many of you worry that it isn’t appropriate.

Trust me when I say that looking contemporary makes me feel younger and fun!!

Adding a scarf to the brim of a hat

Leopard Dress

Let’s first talk about the dress. I love the idea of long sleeve dresses for the cooler days. Granted you can always “make” your own with layering (as I showed with my green velvet dress).

I layered a yellow, short sleeve top under the dress only for a pop of color. I figured the yellow would be easy to pick up in my other extras in the outfit. I’ll discuss that in more detail below.

You might consider this dress a mini dress, however, the secret is it’s not. I hiked up skirt material at the waist and tucked it under the elastic waistband. The reason you don’t see that is the belt covers it nicely.

Insider tip: Don’t automatically assume that these wide elastic belts won’t work for your body type. Try lots of them and evaluate them before you decide. The fact is, each one is different and can work for anyone. BTW, they do tend to “grow” over time when they are hung up. No worries with this one, because I overlapped where it attaches.

Adding in Color With Accessories

With the addition of the yellow top under the dress, it was an easy transition to bring in yellow with my accessories too.

I started with the yellow earrings and once I added the hat, I knew they were perfect. Look how they pop with the color of the hat behind them!!

Of course, the hat needed some extra decoration, so I added a sequin scarf around the headband.

Insider tip: To keep the scarf in place on the hatband, I used clear elastic (found on Amazon here) for the ends of the scarf so it was snug and wouldn’t come undone. Another option is to use a hatpin.

This yellow purse has been a favorite of mine for over 10 years. It’s not a high-end purse, and thus the handles are pulling apart. (You can see the damage in this post).
That is one reason I love adding a scarf to one of the handles. This scarf was made by my mother with leftover material. You can see her blouse of the same material here.

Insider tip: Tying a scarf on a handle of a purse is super easy. I have a short video on YouTube showing you how.

How To Feel Comfortable In Shorter Skirts

Now one answer to this quest might be “don’t wear them.” Haha, and that’s how I was for the longest time. Especially when I was working and trying to promote a professional air about me, I would never have thought to wear a skirt this high above my knee.
Heck, I didn’t even wear shorts after age 30 until just a few years ago.

The next best secret is to wear a pair of shorts under the skirt or dress. This creates a safety net in case the wind pushes your skirt up or just for when you are sitting and moving around. It’s also another trick for an extra layer of warmth.
While I wore a pair of workout shorts, even my mother used this trick this same day but she wore pettipants.

Insider tip: Pettipants (found here on Amazon) is made of a silky material like a slip which is helpful so that a knit skirt or dress doesn’t stick to the shorts.

BTW, I’d like to point out that my thighs are jiggly and crepey. Should I be ashamed and never wear a swimsuit? How sad would that be? Instead, I think of myself as a well-loved Shar-Pei pet where we look at the wrinkles of skin and think “how cute” instead of “gross”.
Our thoughts are VERY POWERFUL, and loving ourselves is a mindset.

Over-the-knee boots and dresses with bare leg showing

Over-the-Knee Boots and Dresses

I chose these olive-colored over-the-knee boots with this dress because they are an older pair that I don’t wear quite as often.
Do you wonder how many of these types of boots I have? Right now I have 6 pairs and they all vary in how high up my thigh they go. In fact, a couple of them are “just” over my knee.

Just like any item of clothing, not all over-the-knee boots are created equally. Even purchasing them in the store can be tricky.
Here are a couple of things I think are important and why I always research the return policy before buying anything:
1-Do they stay up? There are many that the material is too thin to stay up over your knees? Sometimes the thinner ones creep down over time, and it’s annoying to have to adjust them. A little wrinkling around the legs is normal, but I don’t like it when they fall down a lot.
2-Are they flexible or shorter for the back of your knee? Most are made so that the back portion doesn’t jam into the back of your knee, but I’ve encountered a couple that bugs me.

The funny thing about these olive-colored ones. I ordered these online from the young girl’s store Charlotte Russe. Even though they were very inexpensive, they are seriously one of my best pairs. They have a lining inside that makes them thicker and warmer.
It goes to show that a high price tag isn’t always the best option.

Neutral dress with pops of yellow and sparkle

Dresses and Boots

One important detail to remember when looking online at dresses, in particular, is to remember that most models showcasing the dresses are usually very tall. Therefore, if the dress looks like a mini, it may not be that short on you.
If you like the dress, make sure to check the size guide because many times they will tell you the length of the dress and/or the height of the model. This can make a huge difference for how long the dress will actually be on you.

And if the dress or skirt seems a tad short, I’ve written 2 posts about how to style short skirts.
1-The summer version-#5 is my favorite and something so fun.
2-For the winter

Over-the-knee boots and dresses

Photo credit: Rob Filogomo

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