Leather Midi Skirt Outfits

9 Leather Midi Skirt Outfits

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There is no better feeling (at least for this fashionista) when you walk into a store and a piece of clothing inspiration jumps out at you. 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 outfit ideas to showcase its versatility. I am trying something new here, and I hope that you like this refreshed format for my outfit blog posts! 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 post.

Featured | 14K Gold Plated Herringbone Chain Bracelet + ChainsPro Sturdy Stackable Rings Set + ChainsPro Womens Layered Necklace + 18k Gold Filled Chain Ring + 18K Gold Jewelry Coffee Bean Bracelet, U Shape Bracelet, Vintage Mesh Bracelet, Curby Bracelet + 18k Gold Filled Shell Ring + Personalized Initial Necklace + 14K Gold Plated Chain Bracelet + 18k Gold Filled Baguette Cubic Zirconia Set + wowshow Thick Hoop Earrings Hollow 14K Gold Plated Gold Hoops

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.

graphic tee pleated leather midi skirt outfit
graphic tee pleated leather midi skirt outfit
graphic tee pleated leather midi skirt outfit
graphic tee pleated leather midi skirt outfit

Featured | Max Studio Pleather Midi Skirt + CATMICOO Croc Mini Purse + Gladiator Sandal Flat + Tiger Graphic Tee

2. Leather Jacket

Second, I am styling this leather pleated mini skirt outfit around a 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.

leather jacket pleated leather midi skirt outfit
leather jacket pleated leather midi skirt outfit
leather jacket pleated leather midi skirt outfit
leather jacket pleated leather midi skirt outfit

Featured | Max Studio Pleather Midi Skirt + Mini Top-Handle Retro Box Flap PU Leather Satchel
+ CUSHIONAIRE Sasha Boot + VETIOR Deep V Neck Short Sleeve Top + S P Y M Faux Leather Fashion Quilted Moto Jacket

3. Denim Jacket

Third, I am taking a page from the leather jacket idea and going casual with a 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.

denim jacket pleated leather midi skirt outfit
denim jacket pleated leather midi skirt outfit
denim jacket pleated leather midi skirt outfit
denim jacket pleated leather midi skirt outfit

Featured | Max Studio Pleather Midi Skirt + Madewell Kickoff Trainer Sneakers + Chigant Button Down Shirt + Designer Crossbody Bag + ROSKIKI Basic Denim Jacket

4. Work Option 1

Fourth, 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.

how to style a leather midi skirt for work
how to style a leather midi skirt for work
how to style a leather midi skirt for work
how to style a leather midi skirt for work

Featured | Max Studio Pleather Midi Skirt + Amazon Essentials Two Strap Heeled Sandal + Dexmay Envelope Clutch + Pausus Chiffon Button Down Shirt

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.

blazer work wear leather midi skirt outfit
blazer work wear leather midi skirt outfit
blazer work wear leather midi skirt outfit
blazer work wear leather midi skirt outfit

Featured | Max Studio Pleather Midi Skirt + JW PEI FAE Top Handle Crossbody + RASPBERRY PUDDING Cotton Ribbed Tank Top + Dunes Iris braided Heel Sandal + Blazer Jackets for Women

6. Fall/Winter

Next for cute midi skirt outfits is a way to keep the look going into the fall and 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.

sweater pleated leather midi skirt outfit
sweater pleated leather midi skirt outfit
sweater pleated leather midi skirt outfit
sweater pleated leather midi skirt outfit

Featured | Max Studio Pleather Midi Skirt + Rockport Total Motion Adelyn Ballet Loafer Flat + BOSTANTEN Top Handle Satchel + Prinbara Lightweight Oversized Knit Sweatear

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.

layered plaid pleated leather midi skirt outfit
layered plaid pleated leather midi skirt outfit
layered plaid pleated leather midi skirt outfit
layered plaid pleated leather midi skirt outfit

Featured | Max Studio Pleather Midi Skirt+ Triple Zip Small Crossbody Bag + TINSTREE Ankle Boots+ SweatyRocks Long Sleeve Collar Top+ BLACKOO Graphic Top

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.

everyday basic pleated midi skirt outfit
everyday basic pleated midi skirt outfit
everyday basic pleated midi skirt outfit
everyday basic pleated midi skirt outfit

Featured | Max Studio Pleather Midi Skirt + Women’s Over The Knee Thigh High Boots + Calvin Klein Finley Saffiano Crossbody + Fuinloth Basic Long Sleeve T Shirt

9. Animal Print/Statement

Last for leather midi skirt outfits is a fun way to make a statement with animal print! 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.

leopard blouse pleated midi skirt outfit
leopard blouse pleated midi skirt outfit
leopard blouse pleated midi skirt outfit
leopard blouse pleated midi skirt outfit

Featured | Max Studio Pleather Midi Skirt + LJOSEIND Handbag + MARCOREPUBLIC Casablanca Sandals + Women Long Sleeve Casual Leopard Print Top

Leather Pleated Mini Skirt Outfit Frequently Asked Questions – FAQs

Let’s end with some frequently asked questions on how to style a leather midi skirt:

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.

Conclusion

In summary of these leather midi skirt outfits, you are only limited by your creativity when it comes to styling these skirts. Because they look so awesome with a t-shirt, blouse, blazer, and virtually everything, 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. Until next time, continue to let your true beauty shine.

Which idea are you most likely to try?

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Picture of Amanda Vitale
Amanda Vitale
Hi, I am Amanda Vitale, the owner of The Aesthetic Edge. I am a beauty and style expert who has been writing reviews and advice for 10 years. I have had the pleasure of testing hundreds of products, and I have published countless lookbooks. You can see my expertise quoted in top authoritative publications such as Bustle and Real Simple. I have also worked with your favorite brands, such as CurrentBody and AXIS-Y.
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