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For many of us, leather skirts are a brave piece of fashion to wear despite our deep desire to rock the ultra-sexy look. Well, you’ve landed at the right spot as we’ve put together an all-inclusive guide for how to style leather skirts. 

As usual, we’ve taken inspiration from some of the coolest fashion-forward ladies from pop culture to show us the way. Whether you’re looking for an edgier way to style your formal business attire, or want to revamp your street vibe, there are ideas a-plenty awaiting you. 


Classic and sleek: leather pencil midi with a fitted long-sleeved tee or sweater

Celebrity inspiration:  in an episode of “Friends” Rachel Green (played our imaginary best friend Jennifer Aniston) wore a straight, midi-length leather skirt. She paired it with a plain V-neck black top and black boots. This seemingly-simple black outfit was one of Rachel’s most memorable work-friendly outfits and we’re stealing it! 


  • Try a mid or high-waisted leather skirt in a midi-length with a straight cut to keep the silhouette sleek 
  • Play with texture by pairing matte black leather with a soft cashmere long-sleeved top fitted to the waist 
  • If sweaters aren’t for you, choose a cotton or silk button-up shirt tucked into the skirt with the top two buttons left open
  • For Winter-friendly styling, add a tailored coat or blazer 

Don’t forget the Thigh High Over The Knee Boots!

Street-cool: a casual sweater with leather mini or midi, tights and boots 

Celebrity inspiration: Rosie Huntington-Whiteley has been seen strolling the streets wearing many leather skirt outfits from embellished minis with button-up shirts, to plain minis with a basic black tank.

However, our favorite look was a leather midi styled with an oversized, loose knit sweater rolled up at the sleeves and tucked at the front. She paired it with black strappy heels, a sleek updo, and a very chic designer bag. 


  • Aim for the juxtaposition of sleek leather versus a thick, slightly “well-loved” sweater in a rustic knit. If it looks like you just grabbed it off your boyfriend’s floor…even better! 
  • Mini or midi leather skirts work equally as well for this look
  • Make it truly 80s by going for a colored, tiered, high-waisted leather skirt with a combo of suede and shine-finish leather 

For a pop of color try a pair of bold-hued shoes such as magenta strappy heels or metallic gold stilettos 

French-chic: a menswear-style shirt, blazer, and heels 

Celebrity inspiration: you can always count on Victoria Beckham to serve achingly stylish looks, often involving a menswear-style shirt, heels, and sunglasses. Or the classic white blazer look. This is a versatile way to style leather skirts for the office. 


  • Midi-skirts are best for this look, with a straight cut or even a more fitted pencil silhouette (as long as it’s comfy and allows for free and easy movement!)
  • However, if your leather skirt is short (i.e. above the knee) layer with sheer tights, or even try a patterned style for extra textural interest (great for Fall dressing)
  • Make sure your shirt is slightly oversized so that it can be rolled at the sleeves and slightly blousy when tucked into the waistband of the skirt
  • Always go for top-quality cotton when it comes to shirts, your skin will thank you (plus, they last longer)
  • The cut of your blazer depends on your body type and your silhouette preferences. You may prefer a more cropped style fitted at the waist, or an oversized, long-line blazer that flows behind you as you power through the office 


80s Shoe Trends that you need to know about…

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How to Style Leather Jackets…

How to Style Leather Pants

Youthful and fresh: a graphic tee and sneakers 

Celebrity inspiration: the tall and gorgeous goddess Sophie Turner personifies modern cool-girl street style, with an eclectic collection of looks each with a decent dose of grunge.

Sophie often clashes prints, textures, and colors, and opts for chunky boots or sneakers. Let’s channel Sophie and pair our mini leather skirt with a graphic tee and our go-to sneakers for some carefree styling. 


  • Mini leather skirts are best for this look, especially those with metallic embellishments such as buckles or studs
  • Lace crop top or graphic or logo tee works to show the mid section
  • For extra grunge style and textural contrast, try a pair of striped or patterned tights under the skirt 
  • Chunky black Doc martens or well-loved sneakers are epic with this look 
  • Dark sunglasses and messy hair are the perfect finishing touches 
  • For Fall and Winter, try a long-sleeved tee or throw an oversized cardigan over the top 

About The Author

May is totally crazy about the 80s and everything the decade inspired! Having grown up in a household that was totally taken over by 80s music and fashion its only natural that May lives and breathes the 80s!

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