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8 Leather Shorts Outfits Perfect For Transitional Weather

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Leather shorts are a wardrobe must-have for those transitional months, so here are the 8 best leather shorts outfits to wear during the spring and fall for an effortlessly stylish look!

Leather shorts can add a striking, edgy touch to an outfit for a chic look, but they are also one of those pieces in your wardrobe that you don’t quite know how to style or when to wear – so we are here to help you with that conundrum!

We think it’s best to wear your leather shorts during the spring and fall months when the weather is transitioning and it can feel a little cooler than the heat of summer but warmer than the freezing winter months. To help you style these shorts into a stunning look, we have brought together 8 gorgeous leather shorts outfits for you to recreate at home.

There are plenty of different options to suit any personal style, plus day and evening outfits so you can style your leather shorts for any occasion – let’s get started!

How to Wear Leather Shorts

1. Sweater + Shorts

One simple way of styling your leather shorts is to pair them with your favorite sweater to create the perfect spring look! These black leather shorts have been styled with a soft grey boxy sweater, black ballet pumps, and a glossy black shoulder bag for an effortlessly chic, minimalist look that will never go out of style.

Recreate This Look
Light grey Grey Lab Mock Neck Pullover Sweater
Grey Lab

Mock Neck Pullover Sweater

$80 at Nordstrom

Black WeWoreWhat Faux Leather Cuffed Short
WeWoreWhat

Faux Leather Cuffed Short

$98 at Revolve

Black Gucci Jackie Small Shoulder Bag
Gucci

Jackie Small Shoulder Bag

$3,300 at Gucci

2. Monochrome chic

We love the chic, monochrome color palette of this gorgeous leather shorts look! Start out with a pair of high-waisted leather shorts, then add a crisp white button-up shirt, half tucked into the shorts, and layer a grey blazer over the top. Accessorized with a black handbag and black knee-high boots to keep you warm during any cool, transitional weather.

Recreate This Look
White Good American Gender Inclusive Stretch Cotton Blend Button-Up Shirt
Good American

Gender Inclusive Stretch Cotton Blend Button-Up Shirt

$149 at Nordstrom

Grey ASTR the Label Galilea Blazer
ASTR the Label

Galilea Blazer

$168 at Revolve

Black Coach Tabby Polished Pebble Leather Shoulder Bag
Coach

Tabby Polished Pebble Leather Shoulder Bag

$350 at Nordstrom

3. Long leather shorts

Longer shorts are super stylish at the moment so why not opt for some leather long shorts for a trendy look? Style your long leather shorts with a white, high-neck tank-style blouse to create a chic and sophisticated look that you can wear to a work meeting or dinner out. Finish off this outfit with a pair of low-heeled sandals and a yellow top handle bag to bring a pop of color to the look.

Recreate This Look
White Amanda Uprichard Sleeveless Fabienne Top
Amanda Uprichard

Sleeveless Fabienne Top

$150 at Revolve

Black Anine Bing Carmen Short
Anine Bing

Carmen Short

$300 at Revolve

Yellow Miu Miu Wander matelassé nappa leather hobo bag
Miu Miu

Wander matelassé nappa leather hobo bag

$2,750 at Miu Miu

4. Oversized blazers

The silhouette of an oversized blazer perfectly juxtaposes with leather shorts to create a striking outfit that is ideal for an evening out. These mini leather shorts have been paired with a black high-neck top, a black belt to cinch in the waist and black patent pumps then a white blazer is layered over the top to bring an eye-catching touch to this stunning look.

Recreate This Look
Black Anne Klein Short Sleeve Mock Neck Top
Anne Klien

Short Sleeve Mock Neck Top

$59 at Nordstrom

White Ronny Kobo Everlan Blazer
Ronny Kobo

Everlan Blazer

$498 at Revolve

Black Nine West Folowe Half d'Orsay Pump
Nine West

Folowe Half d’Orsay Pump

$99 at Nordstrom

5. All-black

For an effortlessly stylish and sophisticated look, just style your leather shorts in an all-black outfit! An all-black outfit always looks great but the key is to play around with different fabrics and textures, which is why you need leather shorts in your all-black look. Here, the leather shorts have been styled with a black top, oversized blazer, and ankle boots, then a pink handbag brings a pop of color to the outfit.

Recreate This Look
Black SNDYS Hills Blazer
SNDYS

Hills Blazer

$85 at Revolve

Black Vagabond Shoemakers Cosmo 2.0 Chelsea Boot
Vagabond Shoemakers

Cosmo 2.0 Chelsea Boot

$200 at Nordstrom

Gradient pink Dior Lambskin Cannage Gradient Small Caro Bag
Dior

Lambskin Cannage Gradient Small Caro Bag

$3,160 at Fashionphile

6. Animal Print

Animal print always brings a trendy touch to your outfit, and when paired with leather shorts, creates an edgy, glamorous look! This leopard print blouse has been paired with black leather shorts, a black cropped jacket, and black knee-high boots, which keep the blouse the central point of the outfit. Accessorise with gold jewelry and a burgundy bag to add a little warmth.

Recreate This Look
Black and beige leopard print 7 For All Mankind Puff Blouse
7 For All Mankind

Puff Blouse

$178 at Revolve

Black Reformation Trista Jacket
Reformation

Trista Jacket

$298 at Reformation

Black Sam Edelman Sylvia Knee High Boot
Sam Edelman

Sylvia Knee High Boot

$200 at Nordstrom

7. Cozy Coats

When the weather is much colder in the fall months, style your leather shorts with a long, cozy coat for a cute and chic look. These black leather shorts have been paired with black tights, loafers, a black sweater, a long brown coat, and a matching scarf for a polished, minimalist look that is ideal for work or weekends.

Recreate This Look
Brown Akris Punto Wool Blend Coat
Akris Punto

Wool Blend Coat

$1,790 at Nordstrom

Black Superdown Stacie Hot Short
Superdown

Stacie Hot Short

$75 at Revolve

Black Stuart Weitzman Palmer Bold Loafer
Stuart Weitzman

Palmer Bold Loafer

$495 at Nordstrom

8. Sophisticated blouses

As we move from spring to summer, pair your black leather shorts with a sophisticated blouse to create a gorgeous outfit that is ideal for meetings or dinner out with friends. The blue, silky blouse brings a touch of color to the outfit and a little opulence to contrast with the tough leather shorts. Add gold jewelry, black ballet pumps or sandals, and a shoulder bag to finish the look.  

Recreate This Look
Blue Tom Ford Pleated Silk Button-Front Blouse
Tom Ford

Pleated Silk Button-Front Blouse

$1,550 at Neiman Marcus

Black Bardot Belle Paperbag Faux Leather Short
Bardot

Belle Paperbag Faux Leather Short

$88 at Revolve

Taupe Marc Jacobs The Clover Shoulder Bag
Marc Jacobs

The Clover Shoulder Bag

$250 at Nordstrom

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