Fashion

Styling Knee-High Boots and Dresses: Display a Little Leg Action

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The idea of styling knee-high boots and dresses is certainly one way to stay warm while wearing our dresses. Even though most of the women in my area stick to pants, I feel that having the option of wearing dresses and skirts is a great way to keep our looks fresh and not as monotonous.

Quote of the day: “Cautious, careful people, always casting about to preserve their reputation and social standing, never can bring about reform.” Susan B. Anthony

While I didn’t realize I had the gumption to try to reform older women’s fashion with this site, I am up for the challenge. My husband keeps saying that I’m swimming upstream by pushing us out of our comfort zones with our styles.

So what is upstream about knee-high boots and dresses? It’s not super original except for Charlotte, the fact that she didn’t wear matching tights, is a baby step for looking more modern.

As we all know too well, styles keep changing throughout the years, and if we continue to dress the same as we’ve always dressed, we don’t represent our best selves.

Insider tip: You will never regret taking the time to look nice.

Dress: Talbots-thrifted~~ Top: Calvin Klein~~ Boots: SNC Kindell~~ Scarf: ~~ Earrings: from the Denver Art Museum gift store~~ Purse: thrifted

Leg Action with Knee-High Boots and Dresses

Now, obviously, it’s not like Charlotte is showing a lot of naked legs with this look. But that sliver of flesh seems so much more contemporary than wearing navy tights.

I realize that stylists out there will counter that you’re breaking up the leg line and making her look shorter. But since I don’t subscribe to the idea that we should try to look taller, thinner or anything besides what we are, then this look is fabulous.

In fact, one of my favorite outfits on my mom is the last one in this video because of how much leg she is showing off.

Insider tip: Yes, our legs evolve just like the rest of our body but that doesn’t make them bad. Bad is when you don’t appreciate what you have. And some women have lost their legs through trauma or disease. So let’s embrace our wonderful bodies.

Don’t get me wrong. I understand the idea of staying warm in the cold weather, and if it were cold, then I would recommend tights or leggings.
But wouldn’t it be fun to wear a print pair of tights or a contrasting color instead of stressing about if the tights should match the dress or boots?

Scarf and scarf buckle

Layering a Summer Dress

My mom layered a turtleneck under this sleeveless dress which is not much different than my ideas of winterizing your summer dresses which I blogged about here. The advantage of adding a shirt/turtleneck/sweater/sweatshirt under the dress is you don’t interrupt the line of the beautiful dress.

There are so many options you could pair with this red dress for different vibes. My mom wore this white top underneath yet there are other colors that would work.
1-Any neutral would be perfect. A lighter neutral like tan or light grey. OR a darker neutral like black or brown.
2– Do’t forget that a denim shirt would look great too, which I would consider neutral for all intents and purposes.
3-As for colors. Yellow? Yes! Pink? Absolutely! Orange? You betcha!! You get the idea, right?

Notice Charlotte also brought a quilted kimono jacket as an extra topper for the knee-high boots and dress outfit. She made the kimono jacket with the material given to her by a friend.
Of course, she grabbed a jacket to match with the overall red, white, and blue theme which isn’t my favorite (don’t get me wrong, I love the jacket, but sometimes when we overly match everything, it can look too Queen Elizabethish. Not that I don’t like the queen –gosh can I keep my foot out of my mouth?). But for those of you who are matchy matchy, you’ll love that jacket detail.

The Extras That Make This a Cool Outfit

The earrings and the purse are ones that just light my fire in my quest to keep all the old ladies looking cool and hip.

First, the high heel shoe earrings are something my mom found at the Denver Art Museum gift shop when we went to the Dior exhibit. I’ve actually seen them again at other places, but I didn’t buy them because I figure I could borrow them when I want to wear them (like I did here).

Then the bright pink purse is the kind of color contrast that is super fun. In all honesty, my mom grabbed this purse thinking it was red, hahahahaha. But I’m SO glad it’s bright pink instead. I feel like the pop of a different color with the purse is exactly what the outfit needed.

The other accessory is this red, white, and blue scarf. It’s a silk oblong scarf that my mom just draped around her neck and fastened with a scarf buckle clip.

Insider tip: These scarf fasteners make it easy to “tie” your scarf and keep the ends in place. You can find them on Amazon here and here (and they can be worn with a t-shirt to “tie the ends”). OR think about using a belt buckle if there isn’t a prong or it can be removed.

Red and pink in an outfit

Red Fit and Flare Dress

A red dress is definitely one that could be versatile since many of our holidays include red. Christmas, Valentine’s day along with Independence Day all have red as part of their color scheme. Heck, throw in Memorial day plus there’s no reason you couldn’t wear it for a Halloween costume too!

Even though I talked about how my mom was displaying a little leg action with the knee-high boots and dress, you can see that it’s very little bare leg. Just enough to get a glimmer of it when walking and sitting. That’s the perfect baby step if you’re trying something new.

As for this type of dress, I’d call it a fit and flare dress. It’s the kind that is more fitted on the top half and has an a-line silhouette on the bottom half. The advantage of this flowier skirt detail is it makes it much easier to sit in and move around in compared to a more fitted skirt.

Insider tip: The “fit” part of the dress does not have to be tight. You can always go up a size to make it roomier at the bust area. And don’t EVER worry about what size it is. No one knows or cares. What’s important is how it looks and feels.

Related posts:
Red dress with a scarf
Lady in red
Shades of red

Navy boots with red dress

My mom’s original pair of navy knee-high boots were ones that she had dyed.

The story is: back in Denver, she was looking for a navy pair of boots and couldn’t find what she wanted. So she ended up buying a pair of light grey boots. Then she took them to a cobbler and he dyed them navy.
You can see the old navy pair of boots in one of our first year’s posts here.

Insider tip: Cobblers can be a wonderful source of knowledge for your footwear. Many times when shoes “wear” out, you can have them resoled or reheeled instead of tossing them.
Or have them dyed either another color or the same color to make them fresh again.
On top of that, for some heeled shoes that the heel is too high for you, you can have the heel reduced.
Go find a great cobbler in your area and see what they can do!!

The funny part is when we were moving to Arizona, Charlotte purged those navy boots because Arizona is hot, right? Wrong!! Therefore, she searched and found another pair of navy boots because they are a basic item for her closet.
In fact, would it surprise you to know that she has both a flat pair and a pair with a little heel? Now you can see where I get my shopping gene from!

Red fit and flare dress for older women

Are Knee-High Boots Still in Style?

Do you read all of those what’s in and what’s out of style articles?? Many times these are written by young authors who really know nothing about fashion and style.
Even if they are “out of style” does that mean you should get rid of them? Of course, my answer would be a resounding “no”. I think as older women, we realize that not everything we are wearing has to be the newest trend. AND the fact, that all styles will recirculate over time.

My answer of how to wear anything that may not be the “in” thing, is to either wear it in a more modern fashion (if can be) or style it with more fashionable items.
So for this example, the fact that Charlotte is exposing a tidge of bare legs, makes the overall vibe more contemporary.

In all reality, I believe that knee-high boots and dresses are a classic pairing. For those women living in the colder regions, they provide the much-needed warmth and will always look great.

Insider tip: The spring season is a time to get great sales on knee-high boots. If you ever like something from the widget, click the heart and they will email you if the price is reduced.

Knee-high boots and dresses

Photo credit: Rob Filogomo

Thank you for visiting my space on the internet. I like to showcase how it’s never too late to look great for women of any age, size, or working with any budget.
I feel I’m here to help move beyond the fashion rules of yesterday and evolve. Style and clothes are made to give you joy. Not cause us stress because we are worried about what others think.

My hope is that you get ideas and inspiration from Charlotte, Lesley, and myself. It’s not about copying what we wear, but about using what you already have and updating items along the way.
Most of all it’s getting us to think differently and dare I say, have fun?

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