I found an Express pleated leather skirt for under $20 at Gabe’s and recognized its potential instantly as a wardrobe staple. From there, I crafted this look book of nine leather midi skirt outfits to showcase its versatility. As always, you can shop these looks and my everyday jewelry.
Leather Midi Skirt Outfit Ideas
Below you can find my most commonly worn jewelry, which I do wear throughout this look book.
1. Casual Graphic Tee
I am kicking off these leather midi skirt outfits with a graphic tee idea. The look of tucking the shirt in keeps everything polished, and does not hide the belt. A flat shoe is a good idea to keep the look casual, and you can opt for sneakers, slide sandals, so on and so forth. My handbag adds a mini statement and a pop of bling. Just imagine converting this look to leather pants as well! You can read more on that in my leather pants outfit ideas.




2. Leather Jacket
A friend told me long ago that a fashion secret is to create an outfit around one piece, and it really is true! Leather on leather is never a bad idea, but to keep everything crisp and clean, I am pairing the jacket with a basic white crop top. The striped handbag along with the black and white boots allow me to add character to the final ensemble.




3. Denim Jacket
Along with my jacket I am sporting a button down blouse that is tucked in from the front, a crossbody, and neutral sneakers. These skirts are an interesting alternative to leather dresses. I have an entire leather dress outfit look book that you can explore.




4. Work Option 1
I have two work appropriate ideas on what to wear with a midi leather skirt, and I need to share both with you! With option one I am staying clean and classic with a white blouse, a clutch, and heeled sandals.




5. Work Option 2
For the second work option in leather midi skirt outfits I am going layered. This look incorporates a blazer over any shirt of your choosing. I still like the shirt to be tucked in as to not hide any of the details of the skirt. Simply grab your favorite heels and briefcase, and you are off.




6. Fall/Winter
Your favorite sweater is a natural pairing with your skirts. To warm this up more, you might want to layer with tights and booties. My look has more of a dressy feel with ballet flats and a leather handbag.




7. Layered Look
Here is an example of layering, which falls more on the grunge side. I took a cropped graphic tee and wore it under an unbuttoned plaid shirt. From here, studded booties make a simple statement, and the crossbody is a must-have basic.




8. Basic Everyday
I am here to convince you that leather midi skirt outfit ideas are suitable for everyday, as I easily evidence with this number. You can literally grab any plain shirt that you have, throw it on, and you have a look. The black and white handbag breaks up all of the black that I have going on, and the heels add additional interest.




9. Animal Print/Statement
Last is a fun way to make a statement with animal print in your leather midi skirt outfits! This leopard blouse is definitely a standout along with this skirt. I like how the cutout details of the shoes tie into the leopard pattern in their own way. The handbag is small and statement worthy in and of itself.




Frequently Asked Questions
What can I wear with a leather midi skirt?
Since a leather midi skirt is a wardrobe staple, you can wear most anything with it! You can just as easily dress them up for work or a special event, or throw on a sweater to carry it through all seasons.
What top goes with a leather midi skirt?
Any top can go with a leather midi skirt, depending on the end look that you are wanting to achieve. A blouse is great to dress it up, where as a graphic tee is comfy and casual.
Can you wear leggings with a leather skirt?
You can wear leggings with a leather skirt! They will look best with a shorter skirt that ends above the knees. For anything longer, thinner material will look better such as tights or sheer pantyhose.
You can easily argue that a pleated leather skirt is a wardrobe staple and an elevated basic. You can make them work for all occasions and seasons with a little bit of layering. Which idea are you most likely to try? Until next time, continue to let your true beauty shine.

