Chic Leather Shorts Outfits You’ll Love For Day or a Night Out

Wondering how to wear leather shorts or faux leather shorts? You’ll love my style guide filled with leather shorts outfit ideas, including black leather shorts outfit ideas and how to style leather shorts for day and night!

collage of a woman wearing four different outfits with black leather shorts

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Originally published June 12, 2023 – Updated November 15, 2023

Leather shorts have gained popularity over the years as an alternative to the classic leather skirt, and I love this shift. Because shorts are typically more casual than skirts, I find that leather shorts can be styled casually or dressed up more easily whereas a leather skirt is harder to dress down. 

I’m sharing some of my go-to outfits with leather shorts and more cute leather shorts outfit ideas from my fave fashion it-girls. Let’s get into it! 

What can you wear with leather shorts?

Lucky for us, leather shorts can be styled in countless ways; it just depends on the vibe you’re going for. These are some of my favorite pieces to pair with leather shorts:

  • Button-up shirt
  • Tank top or classic tee
  • Chunky sweater
  • Statement top
  • Blazer
  • Denim jacket
  • Trench coat or wool coat
  • Heeled sandals or pumps
  • Heeled boots
  • Ankle booties
  • Dad sandals or slide sandals
  • Chunky trainers
  • Loafers

In my opinion, leather shorts are perfect for a chic and edgy look, so adding a pair to your closet is always a good idea. Whether you prefer classic black leather shorts, brown shorts, or a metallic pair (metallics are all the rage right now), this piece can be worn day and night for a trendy and effortless aesthetic!

Chic Black Leather Shorts Outfit Ideas

Below are some of my favorite black leather shorts outfit ideas to inspire you – and there are looks for any season too!

add a blazer

woman wearing a plaid neutral blazer over a black top with black leather shorts and black knee-high boots

get the look:

In my experience, black leather shorts can be styled in a chic and sophisticated way with a blazer. With this combo, you can wear knee-high boots for a going-out look, or loafers for a business-casual vibe. Or, go with sneakers for a casual, sporty twist. 

neutral tones

woman wearing a chunky ivory knit sweater with black leather shorts and black knee-high boots

get the look:

Here is another excellent way to style leather shorts for cooler days, especially the transitional weather in early fall or early spring. The ivory sweater and tall black boots are perfect for cool weather, while the leather shorts add a chic touch. 

I love how this outfit is simple to put together but still looks polished, and the neutral colors give this look effortless style. This outfit is great for exploring some new hot spots in the city on a crisp day.

holiday ready

woman wearing a chunky red cable knit sweater with black leather shorts and black knee-high boots

get the look:

The holiday season is the perfect time to sport your leather shorts, in my opinion! 

Here I’m wearing a pair with a chunky cable knit sweater in vibrant holiday-inspired red and black knee-high boots. I would also add sheer black tights to this outfit for an evening look. 

trench coat + tall lug boots

a woman wearing black leather shorts with black stockings, a long-sleeved white and black striped top, a trench coat, and tall black boots
@_jessicaskye

get the look:

I love this black leather shorts outfit by @_jessicaskye!

There are so many pieces here that make this outfit fall-friendly – from the sheer tights to the tall boots and trench coat. I love the combo of a simple long-sleeved shirt with these black leather shorts. It’s the perfect base to have and you can take off the trench coat if it gets too hot. 

brown leather shorts outfit

a woman wearing brown leather shorts with a white tee, a tan blazer, and white booties
@natmpham

get the look:

This leather shorts outfit by @natmpham is oh-so-chic and a perfect look for fall!

The warm brown tone of the leather shorts screams autumn, and the plaid blazer is also very fitting for the season. I love the ankle booties but think tall-heeled boots in a cream color would work great as well.

Summer-Approved Leather Shorts Outfit Ideas

In the summer months, you can easily wear leather shorts, you just have to pair them with the right pieces! Below are a couple of great ideas. 

keep it simple

woman wearing an oversized white t-shirt with Jil Sander text and black leather shorts with black loafers

get the look:

My summer leather shorts outfit is simple but incredibly chic. You can’t go wrong with a classic white tee and loafers, in my opinion. These basic pieces let the leather shorts be the star of the outfit. 

The black loafers keep this look classy and are also perfect for running errands or grabbing lunch with friends. For an extra layer, I’d throw on an oversized denim jacket or a tie a knit sweater around my shoulders.  

dad sandals + a denim shirt

a woman wearing black leather shorts with a blue denim button-up, black dad sandals, and a plaid tote bag
@bubblyaquarius

get the look:

This gorgeous leather shorts outfit by @bubblyaquarius is perfect for grabbing an iced matcha and doing some retail therapy. The light blue denim shirt adds a vibrant pop of color when paired with black leather shorts, and the dad sandals add a chill but stylish vibe that I adore.

I think you can definitely rock this outfit on a summer day or in early fall before it gets too cold.

Night Out Leather Shorts Outfit Ideas

Looking to wear an eye-catching piece for girl’s night? These night-out leather shorts outfit ideas below are perfect!

add a statement top

woman wearing a cream embroidered silk button up shirt with black leather shorts and black suede pumps

get the look:

An elegant and feminine blouse goes perfectly with bold and edgy black leather shorts. Here, I’m wearing my silk Toteme button-up top with leather shorts and black suede pumps. 

While my top is on the more conservative side, you could easily go with a camisole top, glittery top, crop top, or printed top instead. And if it’s going to be a cool evening, wear sheer black tights! 

Finish the look with statement earrings and you’ll (guaranteed) be stealing the attention all night.

leather bermuda shorts

a woman wearing black leather shorts with a black crewneck tank, strappy black heels, and a black handbag

get the look:

Longer leather shorts are having a moment right now and make for a stunning black leather shorts outfit for a night out. Paired with sleek black pieces and strappy heels, this is another outfit that’s easy to put together but definitely makes a statement. 

I love the all-black look, but you could also add some color if that’s more your style. Try adding a pop of color with your shoes or purse!

faux leather bike shorts

a woman wearing black leather biking shorts with a black top, a denim jacket, and ankle wrap black leather
@nicoleakhtarzad

get the look:

Biker shorts have been a hot trend in the fashion scene over the last few years. And faux leather biker shorts are perfect for a night out, in my opinion!

This outfit has a laid-back vibe that I love but is still fashionable enough to wear during a night on the town. Strappy black heels elevate this look, and the denim jacket is perfect for chilly nights.

vibrant shades

a woman wearing brown snakeskin leather shorts with a blue sweater vest, orange heels, and a blue handbag
@fashncurious

get the look:

When you’re going out for the night, it’s never a bad idea to wear a pop of color. Brown leather shorts are more subtle, but you can quickly create an eye-catching outfit by pairing them with bright blue or hot pink.

I love the combo of brown leather and blue pieces above; these shades complement each other so well and have a gorgeous contrast that immediately draws attention. 

metallic leather

a woman wearing silver leather shorts with a black top, a brown suede jacket, and black strappy heels
@desa_1972

get the look:

Metallic clothing and accessories were one of 2023’s biggest trends, according to ELLE Magazine. While I have yet to jump on the train myself, I have been particularly drawn to metallic leather pants and footwear. 

This look shows just how great silver leather shorts would look for a night out. The silver pops against the black top and brown suede jacket, and the silver statement necklace creates the perfect balance.

matching leather set

a woman wearing black leather shorts with a matching black leather cropped top with long sleeves, strappy silver heels, and a black leather handbag with crystal embellishments
@carolynabauer

get the look:

Lastly, a matching set is an easy go-to for a stunning and effortless night-out look. 

If you don’t have a matching set, you can always pair your leather shorts with a leather crop top or leather jacket for a similar look. Nonetheless, this outfit has a sexy and feminine feel that will have you turning heads all night!

 

I hope you have enjoyed this list of leather shorts outfit ideas for spring, summer, fall, and winter. Follow the links below for more outfit inspiration! 

 

More Style Guides You’ll Love:

17+ Leather Pants Outfit Ideas That Prove You Need A Pair

What to Wear With A Leather Jacket

How To Style A Leather Blazer

How To Style Shorts with Tights

What To Wear With Faux Leather Leggings: Chic Outfits To Try

Best Tops To Wear With Leather Leggings

About

Hi! I'm Christal - Editor-in-chief, published author, and minimalist fashion enthusiast! Welcome to Style Your Occasion, your styling inspiration go-to for every occasion, event, party, and trip! Click below to meet the rest of the Style Your Occasion team.

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