My Top Five Skirt Wearing Tips: Mom Style Files #MSFILES


When I was younger, skirts weren’t my thing. In fact, I dressed like a Tom-Boy, bell bottom jeans and flannel shirts {it was the early seventies} I went on this way almost through high school. Wearing sloppy sweat pants, jeans and lots of leggings. Skirts didn’t make huge appearance in my wardrobe until I reached the working world.

It was against the rules to wear shorts, so the only way to beat the heat at the office was by wearing a skirt. Of course this was back in the day, when pantyhose {aka manmade torture device} were mandatory so being “cool” was still subjective, but it was better than wearing black pants.

As the working world became more progressive I was able to drop the pantyhose and wear open toed shoes. This was the tipping point for me and skirt-wearing, and once the warm weather started the skirts were busted out of my closet.

I soon realized that I couldn’t contain my skirt love just to one season. So I bought some tights and tall boots and started winterfying some of my spring and summer skirts.

 Spring to Fall Skirt

Now I wear them year around, I have over 40 skirts in my closet. From the figure forgiving A-line to the formal pencil skirt, to the casual carefree run around town knit skirt.

Of course I can never have too many and I think this summer a maxi skirt, like this one from Target, is calling my name.


Target Maxi Skirt

I might venture out side the box even further and purchase a sport skirt like this one from Albion

albion pleat_green skirt

So, are you ready to skirt it up with me? There’s still time to participate in our skirt challenge. Here are some of my top five skirt wearing tips to get you started…

1. Leggings make transitioning to skirts easier.

For those of you who are struggling to wear a skirt, try a pair of leggings under your skirt instead of tights, it will be just like you are wearing pants.

2. Don’t save your spring skirts just for spring.

Here’s one of my favorite spring skirts that I turn into a cute fall skirt with just tights, a long-sleeve shirt and boots. Easy Peasy.

3. Skirts don’t have to be just for a special occasion.

I don’t save my skirts for work or date night, a casual trip to the grocery store can be the perfect place to wear one.

4. If you have an issue jean shopping you won’t skirt shopping.

I have tiny waist and wider hips so buying pants is a total pain. But skirts are so easy, especially A-line styles that glide right over those hips and accentuate my tiny waist. Win, Win!

5. A simple black skirt is the perfect place to start.

A black skirt in a comfortable fabric with a flattering cut {I like the a-line} will give you a blank canvas for any season.

You could pair it with flats and a button down for the office.

Office Black Skirt


Sandals and t-shirt for casual grocery run.

Casual Black Skirt


A Glittery top and heels for a night on the town.

Night Out Black Skirt

It’s like a pair of jeans only cuter.

Overall, when wearing skirts it’s about having fun! Consider it one more accessory in your wardrobe arsenal, and seriously don’t you want more reasons to go shopping, I know I do…


If you are taking our skirt challenge, be sure to tag your photos with #MSFILES or your can tag @RedheadReverie or @PBinmyhair in your post.


  1. […] hope you feel the same way. Between My Top 5 Skirt Wearing Tips and Peyton Price’s skirt haikus and advice, you should be well on your way to to bare those […]

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