10 Leather Jacket Outfits to Try Now

Getty Images: Christian Vierig
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10 Leather Jacket Outfit Ideas to Try Now

Getty Images: Christian Vierig

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. In fact, there are few leather jacket outfits that don't work. Have you ever worn yours with a cocktail dress or a maxi? Or how about with an Americana-inspired bandana for a look that's just a little 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. 

Ahead, we rounded up stylish street style outfits to give you all the inspiration you need to know how to wear a leather jacket with style, any time of year.

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

Getty Images: Kirstin Sinclair, Melodie Jeng, Vanni Bassetti

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

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2. Try a Colorful Leather Jacket.

Getty Images: Edward Berthelot, Daniel Zuchnik

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 even 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.

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3. Embrace a Full Americana Look.

Getty Images: Kirstin Sinclair

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!

*For more tips on rocking a bandana this spring, click here.

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4. Play with Proportions in an Oversized Jacket.

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 and 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.

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5. Put a Ladylike Spin on the Leather Jacket.

Getty Images: Kirstin Sinclair, Melodie Jeng

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

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6. Style Your Leather Jacket over a Maxi Dress.

Getty Images: Daniel Zuchnik, Melodie Jeng

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 the way this combination brings together edgy and romantic elements for a very cool balance—no matter what season!

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

Getty Images: Vanni Bassetti, Rabbani and Solimene Photography

For the Met Gala in 2013, 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.

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8. Give the Shearling-Lined Leather Jacket a Try.

Getty Images: Melodie Jeng, Christian Vierig, Daniel Zuchnik

​During the winter months, 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 (both cropped and oversize) look when paired with 70s-inspired elements like bell bottom jeans and striped fitted sweaters.

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9. Pair a Leather Jacket with Your Workwear Separates.

Getty Images: Vanni Bassetti

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

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

Getty Images: Edward Berthelot, Marc Piasecki

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, a la Kendall Jenner, and throw your leather jacket on over your workout attire.