Woman over 50 wearing a short skirt

The Bottom Line on Shoes to Wear- With Short Skirts

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Woman over 50 wearing a short skirt

The Bottom Line on Shoes to Wear- With Short Skirts

Ending our theme of the week, I was chosen by Lesley and my mom to showcase which shoes to wear with short skirts. While most of us aren’t wearing as many short skirts after we turn 50, my shoe choices could all work for other length skirts too!

Quote of the day: “Knock me down nine times, but I get up ten.” Cardi B.

This quote is a good reminder to me that when we try a certain style or item and don’t like it, it’s not always good to just give up. So many times, there are other details that can make it successful.
For example, when clothes don’t fit just right, having them altered is key like my mom explained in a previous post. Sure, it’s a pain or it can be pricey, but it’s worth it.
Even for shoes, as Lesley shared recently, finding the hacks to make them fit better makes for less “Cinderella” moments.

I found some great ways to showcase my shoes to wear with short skirts and still be modest and covered. In fact, even though my skirt is relatively short, you won’t be seeing much skin!!
And even I had a wild card shoe type that was hard for me to style. It’s the last option.

Make sure to see the other lengths of skirts with different shoes
4 Options of Shoes with Skirts- A Spotlight on a Knee Length Skirt
4 Popular Options-Shoes to Wear with a Long Skirt

Skirt: Tobi ~~Top: Rubbish ~~ Earrings: Mariposa Skies

OTK boots as shoes with wear with short skirts

Over the Knee Boots

This is actually my favorite kinds of shoes to wear with short skirts. In a way, it’s like they were made for each other. You still get the coverage since the boots come up higher on your leg. One of the nice aspects is you can forgo any hosiery or tights with this option.

While it’s modern to show a bit of leg between the skirt and boot, you don’t have to. This would look just as cute with a longer skirt.

You can see how both Charlotte and Nancy wore their taller boots in the past.

Shoes to wear with short skirts including booties

Ankle Boots

I just love ankle boots with a skirt and I have worn them multiple times on this blog. Remember, there are a ton of different kinds of ankle boots. For example this pair (from Jambu) is very low cut so it’s really at my ankle. I have others that come up higher on the leg.

To keep this from showing too much leg, I wore some whimsical printed tights. I realize that if you do wear tights, you may only have the basic colors. However, why not add at least one fun pair?

Insider tip: If you’re not a fan of ankle boots with your skirts, the tights could end up being the focal point!! It’s like being a magician and distracting the audience by having them look at the tights instead of the boots.

Shoes to wear with short skirts-sneakers

Sneaker Shoes to Wear with Short Skirts

Functionality is truly key for most of us when getting dressed, so pairing a skirt (which can be easier to fit and easier to move around in) along with comfortable sneakers is an obvious yes.

For this version, I wore athletic sneakers since Lesley wore more fashion oriented sneakers. Again, I added in some fun and personality with my teal tights (which are fleece lined by the way).

Insider tip: Lightweight sneakers are the new trend, and we’ve tried out two different brands. These grey ones are from AKK (post here) and we’ve also tried Tiosebon (post here).

Winter boots with tights

Winter Boots

Since it’s winter, another great option of shoes to wear with short skirts is a pair of winter boots. Granted, I don’t have as many now that we moved to Arizona, but these Jambu ones (worn here) are perfect.

Insider tip: What I like to do when the ankle opening is wider than my ankle is to scrunch down my socks to fill in the gap. BTW, I “borrowed” a pair of my hubby’s socks for this.

Combat boots as shoes to wear with short skirts

Wild Card Footwear

I’m seeing combat boots all over Instagram on older and younger women alike. Even though I have this pair and recently wore them with my longer vest, I have trouble styling them. I still struggle with the fact that they seem so bulky and clunky.
Because they aren’t my go-to boots, I decided to challenge myself on more ways to wear these. Keep your eyes peeled.

And if you don’t think you’d ever wear these kinds of boots, I get it. But if they were comfy, maybe it’s a great option that seems like a younger vibe than some of the old lady shoes and boots I see??

5 shoes to wear with short skirts

Photo credit: Rob Filogomo

My Goal

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 other’s think.

My hope is that you get ideas and inspirations 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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