There’s just something effortlessly chic about an oversized leather jacket – it instantly transforms any outfit with that mix of edge and sophistication. Whether you’re layering it over a feminine dress, pairing it with sleek trousers, or keeping it casual with denim, this piece always makes a statement.
Unlike fast-passing fads, oversized leather jacket outfits are having a real moment right now because they’re versatile, comfortable, and oh-so-stylish.
What makes them even more exciting? You can play with balance. An oversized leather jacket looks amazing thrown over a mini skirt for contrast, styled with tailored pants for polish, or layered with cozy knits when the temperature drops.
Here are my absolute favorite oversized leather jacket outfits I’m completely obsessed with at the moment and I’m sure you’ll love them just as much as I do!
20+ Stunning Leather Jacket Outfits You’ll Love
Burgundy Leather Jacket with Black Pleated Skirt
This leather jacket paired with a chic black skirt and those adorable Mary Jane shoes is a killer combo. The jacket’s deep burgundy shade adds a touch of sophistication, while the white socks give it a playful twist.
Oversized Brown Leather Jacket with White Mini Skirt Outfit
This leather jacket outfit is a chic blend of edgy and feminine vibes. The oversized brown leather jacket paired with a delicate white lace dress creates a perfect contrast that’s both bold and stylish.
Vintage Brown Leather Jacket with Straight Leg Jeans
The oversized leather jacket paired with light-wash jeans is a classic combo, effortlessly blending edgy and casual vibes.
Brown Leather Jacket with Blue Button Down and Leopard Print Pants
This leather jacket outfit is such a cool mix of edgy and casual. Pairing the oversized, vintage-style jacket with a classic blue button-up and bold leopard print pants creates an effortlessly chic fun contrast. I love how the red bag adds a pop of color, making the whole look stand out even more.
Brown Leather Jacket with Brown Mini Skirt
This leather jacket paired with a simple white tee and chic mini skirt perfectly blend edgy and casual.
With a Denim Skirt and High Leg Boots
This leather jacket paired with a sheer top and high-waisted denim skirt is such a chic combo. I love how the sleek black accessories, like the sunglasses and bag, tie the whole look together. It’s edgy yet effortlessly stylish, perfect for making a statement on the streets.
Cropped Leather Jacket with a Mini Skirt
This leather jacket outfit is chic with the matching mini skirt and sleek black boots. The oversized jacket adds a cool, laid-back vibe, while the fitted top keeps it effortlessly stylish. I love how the sunglasses and simple accessories combine the whole look for a perfect street style moment.
Burgundy Leather Bomber Jacket with a Blue Button Down Shirt
Combining a rich brown leather jacket with a crisp blue shirt and white pants is effortlessly chic. I love how the jacket adds a touch of edge while the shirt and pants keep it fresh and clean. The small black handbag is the perfect accessory to tie it all together, making it a standout look for any casual outing.
Oversized Brown Leather Jacket with Mini Denim Skirt
The oversized leather jacket paired with a sleek gray top and edgy black denim skirt creates a cool, effortless vibe. I love how the pointed heels add a touch of elegance, balancing the jacket’s ruggedness. It’s a perfect mix of casual and chic, making it ideal for a day out or a night on the town.
Brown Leather Jacket with Black Straight Leg Jeans
This leather jacket outfit is effortlessly chic. It pairs perfectly with dark jeans for a laid-back yet polished look. The scarf adds a cozy touch, making it ideal for a casual day out. I love how the sunglasses and sleek bun keep the vibe cool and sophisticated.
Short Burgundy Leather Jacket with Black Jeans
This leather jacket is a total statement piece with its rich, deep burgundy color and oversized fit. I love how it pairs perfectly with the sleek black outfit and the matching bag, creating a chic and cohesive look. The bold accessories, like those chunky gold earrings and sunglasses, add just the right amount of glam.
Beige and Brown Detailed Outfit
This leather jacket outfit is a chic blend of edgy and cozy vibes. The oversized brown leather jacket paired with a chunky knit sweater and pleated skirt perfectly balances warmth and style. I love how the knee-high socks and casual slip-ons add a playful touch, making it ideal for a stylish coffee run.
Leather Jacket with Wide Leg Leopard Print Jeans
The oversized leather jacket paired with those bold leopard print pants is a cool mix of edgy and playful. I love how the red sneakers add a pop of color, perfectly matching the hair accessory for a fun twist. It’s a look that feels effortlessly stylish and unique!
Brown and Blue Details Outfit
The oversized leather jacket paired with relaxed jeans and retro sneakers creates a cool, laid-back vibe. I love how the earthy tones of the jacket and shoes complement each other, making it perfect for a casual coffee run. The chic green bag adds a touch of texture and style, tying the whole look together effortlessly.
Brown Bomber Jacket with Wide Leg Blue Jeans
This leather jacket paired with a cropped white top and relaxed jeans is such a cool, effortless look. I love how the jacket’s oversized fit adds a touch of edge, while the sneakers keep it casual and comfy. The small handbag and sunglasses tie everything together perfectly for a chic, laid-back vibe.
Brown Bomber Leather Jacket with Black Jeans
This leather jacket paired with wide-leg jeans and sneakers is a cool, laid-back look. I love how the oversized fit adds a touch of effortless chic, and the pop of red from the bag gives it just the right amount of edge. Plus, those sunglasses are the perfect accessory to tie it all together.
Brown Leather Jacket Outfit with Brown Jeans
This leather jacket outfit is such a chic blend of sophistication and edge. The deep brown tones create a seamless look, perfectly complemented by the sleek handbag and pointed shoes.
FAQ:
How to look good in an oversized jacket?
The key is balance. Pair an oversized leather jacket with slim jeans, tailored pants, or a mini skirt. If you want variety, try switching things up with a cropped leather jacket outfit for a more fitted look.
What not to wear with a leather jacket?
Avoid overly bulky pieces that compete with the jacket’s volume. Instead, stick with sleek basics that let your oversized leather jacket outfits shine.
Are oversized leather jackets in fashion?
Absolutely — they’re one of the biggest outerwear trends right now. Fashion insiders love mixing classic styles with updated silhouettes, including the cropped leather jacket outfit trend.
Is 40 too old for a leather jacket?
Not at all! A leather jacket, oversized or cropped, is timeless. It’s all about how you style it. A cropped leather jacket outfit paired with tailored trousers can look polished and age-appropriate.
What pants to wear with an oversized jacket?
Straight-leg jeans, slim trousers, or even leather pants work perfectly. Just make sure they balance the volume of your oversized leather jacket outfits.
Are oversized blazers still in style in 2025?
Yes – just like oversized jackets, they remain a go-to. A cropped leather jacket outfit can also be a great alternative when you want a structured yet edgy look.
How to not look frumpy in oversized clothes?
Highlight your shape by pairing your oversized leather jacket outfits with more fitted bottoms or accessories that define the waist. Adding a cropped leather jacket outfit into rotation can also help.
Are oversized jackets still in style?
Definitely. From oversized leather jacket outfits to cropped leather jacket outfit looks, both styles are trending and offer endless styling options.