There are few pieces of outerwear that have reached “grail” status to such a degree as the leather jacket. First worn by army pilots and soon coopted by socialites and movie stars in the first half of the 20th century, the leather jacket signifies cool more than any other article of clothing.

By now, we all know that it works well with our most basic and classic wardrobe staples, like black pants and jeans.

There are a few leather jacket outfits that don’t work. Have you ever worn yours with a cocktail dress or a maxi? How about with an American-inspired bandana for a look that’s just a bit retro? This moniker of “cool” can serve many purposes—add a little edge to a lady-like ensemble or give your favorite workwear staples weekend wearability. 

We’ve gathered a collection of stylish street-style outfits to provide you with all the inspiration you need to know how to wear a leather jacket with style at any time of year.

“The global jacket and coat market was forecast to generate around 94.5 billion U.S. dollars in retail sales by 2021, up from around 81 billion U.S. dollars in 2016. Jackets and coats are a segment within the overall apparel market. As the global apparel market grows, it is unsurprising that sales of coats and jackets will also rise” (P. Smith, Nov. 1, 2021, Statista).

1. Classic With a Twist: Wear Your Leather Jacket with Jeans

We know—wearing jeans with your leather jacket is a no-brainer. But instead of keeping it traditional (skinny jeans, a simple top), why not get creative with this combo? Take some inspiration from the street-style shots above. Try layering faux fur over your shoulders or wearing a cropped jacket with a shirt with extra-long sleeves.

2. Try a Colorful Leather Jacket

Black leather is a classic and goes with everything, but don’t rule out other playful colors for your secondary leather jacket, like a rich blue or olive green. Here, lifestyle blogger Aimee Song styles her leather moto jacket with a mini skirt and over-the-knee boots with a dash of floral print for a playful, Fashion Week-worthy look.

3. Embrace a Full Americana Look

Want to feel like a true biker babe in your leather jacket? Try wearing yours with a classic denim shirt, bandana, and leather boots. We love how distinctly American Joanna Hillman looks here, especially given that she’s layered up in Iro and Saint Laurent—which are French labels!

4. Play with Proportions in an Oversized Jacket

Leather Jacket Outfits to Try Now: Play with Proportions in an Oversized Jacket.
(Photo Credit: Getty Images: Christian Vierig, Edward Berthelot).

This oversized, shearling-lined leather jacket from Acne has quickly become the go-to winter jacket for the model-off-duty and Fashion Week set. The exaggerated proportions make it an ideal topper for skinny jeans, ankle boots, or even a pencil skirt and heels. For those feeling slightly more daring, go “full fashion” and style it over a matching pajama-style top and trousers.

Get tips on the pajama dressing trend.

5. Put a Ladylike Spin on the Leather Jacket

Why not toss a leather jacket over your shoulders in place of a cardigan? The same goes for wearing yours with ladylike pieces such as a full midi or tea-length skirt, floral prints, or a ruffled-hem dress. Just replace the “expected” piece with a leather jacket for a more youthful spin on a traditionally girly look.

6. Style Your Leather Jacket over a Maxi Dress

Transitional season dressing tip: Take leather into spring (and even early summer) by wearing your moto jacket over your favorite maxi dress. Or, do the reverse and make a more summer-y maxi dress work in the fall by layering it with a cropped leather jacket. We love how this combination combines edgy and romantic elements for a very cool balance—no matter what season!

7. Add Edge to an Evening Look with a Leather Jacket

For the Met Gala, Sienna Miller embraced the “punk” theme by rocking a studded leather moto jacket over a sleek, minimal white evening dress. While we might not attend such a swanky event in our lifetimes, we can take a cue from Ms. Miller and try wearing our favorite leather jacket over some of our dressy cocktail frocks for city weddings, dressy date nights, and parties.

8. Give the Shearling-Lined Leather Jacket a Try

Give the Shearling-Lined Leather Jacket a Try
(Photo Credit: Getty Images: Melodie Jeng, Christian Vierig, Daniel Zuchnik).

During the winter, the most stylish way to upgrade (and update) your leather jacket wardrobe is to track down a jacket with shearling lining or collar details. Not only does the soft, fuzzy shearling add warmth to your look, but it also adds a trendy touch. We love how these jackets (cropped and oversized) look when paired with 70s-inspired elements like bell-bottom jeans and striped fitted sweaters.

9. Pair a Leather Jacket with Your Workwear Separates

If you want to add a little edge to your 9-to-5 wardrobe, layer a leather jacket over your suiting pieces, including pencil skirts, cropped trousers, and button-up shirts. This is a great way to take your workwear pieces from day to night; substitute your blazer for your biker jacket, and you’re ready for happy hour.

10. Wear it Like a Model-Off-Duty: With Anything!

As we mentioned at the start of this post, the leather jacket is an iconic wardrobe staple. For this reason, there really are no rules about how to wear a leather jacket or the best leather jacket outfits. You can take a page out of Gigi Hadid’s book and wear yours over a sweatshirt and sweatpants, or do like Karlie Kloss and wear it over a cute t-shirt and skirt. Or, take it a step further, à la Kendall Jenner, and throw your leather jacket on over your workout attire.


What to wear with a leather jacket in 2023?

In 2023, leather jackets are a fashionable wardrobe staple for women and men. They come in a variety of styles, such as oversize, moto, bomber, blazer, shacket, cropped, and long, and can be worn with anything from jeans and a t-shirt to a little black dress or jumpsuit.

Women over 40 can also wear leather jackets with stylish combinations, such as a black leather jacket paired with a striped top and grey maxi skirt.

How do you dress a leather jacket?

A leather jacket can be dressed up with dress slacks and dress shoes, and the color of the jacket should match the footwear.

Pair it with jeans, a t-shirt, a mini skirt, and a top for a more casual look. Avoid boots, wider pants, collared shirts, and anything formal.

Leather is also known for its protection from physical harm and the elements. Women over 40 can wear leather jackets with a classic fit paired with a striped top and maxi skirt.

Are leather jackets in style in 2023?

Leather jackets are in style for 2023 and will remain so for the next decade. They come in a variety of styles, including bomber, racer, field, flight, and biker jackets, and can be paired with a girly midi skirt for contrast. Bold colors are in style right now, and faux leather or vegan leather is a more eco-friendly choice.

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