How to Style a Pleated Skirt or Any Difficult Piece

How to Style a Pleated Skirt or any Difficult Piece | Style by Toyin

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This look is actually a throwback from Mother's Day from 3 years ago, but as I was looking through my closet, I realized that this would make a great teaching outfit for me...minus the heels. I have to trek too far across campus for all of my classes to then stand for an hour in heels.

I remember this outfit well because the skirt (shoppable links at the end of the post) is something my mom bought me. However, I wasn't able to wear it because I couldn't figure out how to style it! I had this same issue a while back with a scarf ! It took me about an hour of trying every top and cardigan in my wardrobe before I finally figured out how to style a pleated skirt!

I paired it with this cute chambray shirt (similiar here) I got years ago from New York & Company and these army green sandals (similar here). I finished the look with this fringe purse , which was a big deal because I rarely switch out my handbags.

In the end, my mom really loved my outfit and a girl at my church said that I gave her inspiration on how to style the skirt. She has the same one and, like me, couldn't figure out how to wear it!

Do you have something in your closet that you don't know how to style? 

2 Methods for Styling a Difficult Piece


We all have at least one item in our wardrobe that we love but just can't figure out how to style or what would look right with it!  Like my pleated skirt.  But after using my two methods, I've found multiple ways to wear that skirt, three years later!

Pleated skirt leather jacket | How to style a difficult piece | Style by Toyin

Have a Fashion Show in Your Own Closet

Just going into your closet and holding up items of clothing next to your "difficult piece" is not enough!  You have to figure out what shape the pieces are going to create together as well as how you feel in them.

So my first method for figuring out how to style a difficult piece is to go in your closet and try things on!  Try on complete outfits, shoes and everything!  It makes a difference!  When you try things on, you'll notice little things like, oh, this looks best tucked into something with a higher waist.

And that will lead you to something that will work.

Pinterest Research

One of the best things about Pinterest is that it is a search engine.  It's so easy to find exactly what you want!  Every fashion blogger posts their outfits on Pinterest so all you have to do is type in the name of your difficult piece.

For example, if I type "pleated skirt" in the search bar, these are my results.

Pleated Skirt | How to Style a Difficult Piece

This is probably where I got the idea to pair my pleated skirt with my leather jacket!


I hope this post helps you figure out how to style that new piece you love but can't figure out how to wear yet!  If you need more suggestions, you are welcome to join my private Facebook group called Styled with Intention.  I'm in there everyday giving style tips and advice.  Click here to join the group!


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