12 Ways to Wear an Oversized Leather Jacket

When it comes to fashionable statement pieces, bigger is better. And what better example than a leather jacket? Leather jacket outfits have had their fair share of makeovers throughout the years. From the leather biker jacket reminiscent of the 1978 cult classic film Grease to the trench coat version in the '90s, the leather jacket has circled the trend block again — this time in an oversized silhouette.

We love a cropped moment with leather jackets, but there is something truly special about an oversized leather jacket. As celebs like Hailey Bieber and Florence Pugh have proven, they act as the perfect style safety net. Thanks to their extra volume, oversized leather jackets make great security blankets when it comes to trying out experimental looks that might otherwise feel like too much of a fashion risk. From sheer dresses to micro-mini hot pants, there is no hemline too high or 'fit too outrageous to pair with this outerwear staple.

As much as we love using oversized leather jackets as a fashion support system, there are subtle ways to wear them as well. Plus, they can dress outfits up or down since they add instant polish or an edge, depending on what you're wearing. 

Read on for our 12 favorite takes on the oversized leather jacket, from risky to ultra laid-back.

With Sheer Tights and Loafers

Bieber just might be singlehandedly responsible for revitalizing the oversized leather jacket outfit simply because she's rarely photographed in any other outerwear. One of her go-to outfits is the TikTok-approved combination of sheer tights, ankle socks, and square-toed loafers. Is she wearing other clothes? Absolutely. Do they matter? You be the judge.

With White Denim and Converse Sneakers

An elevated and casual take on the oversized leather jacket outfit, this look featuring white jeans and Converse sneakers can be dressed up or down depending on what accessories you work into the outfit. Add a quilted designer bag for a Fashion Week guest vibe, oversized sunglasses for an editorial moment, or a baseball cap to keep things down-to-earth.

With an LWD

A little white dress is just as much of a wardrobe essential as a little black dress, and we are frankly insulted on its behalf for the lack of attention it receives. What better way to celebrate this underrated staple than pairing it with an oversized leather jacket and some platform biker boots?

With Leather Pants

Distinctly different from the vampy vibe served by a cigarette pant, a wide-leg leather pant manages to be both casual and quietly luxurious. We like how this looks cozy but elevated with the addition of a designer handbag, statement sneakers, and an alt-girl hoodie.

With Lace Pants

Ease your way into the season of showing skin by wearing an oversized leather biker jacket with a little — or a lot of — lace. A black pair of lace pants will offer you the most coverage, while brighter shades are a bit more daring. Whatever color you choose, you're definitely headed for a main character fashion moment.

With Wide-Leg Jeans

Wide-leg jeans and a crop top are one of Bieber's oversized leather jacket staples, and we love her for it. So simple but still chic and replicated by TikTok stars and Gen Z influencers worldwide, this combination is worth adding to your vision board ASAP.

With Statement Tights

This look may be the edgiest on our list, and it's all about one accessory: statement tights. As the centerpiece of the look, the tights of your choice will dictate the rest of the outfit. We love the deconstructed Marie Antoinette moment from the beribboned tights, especially when paired with pastel heels and an oversized leather moto jacket.

With a Lingerie-Inspired Slip

A lingerie-inspired slip dress in black silk creates a beautiful balance between femininity and structured menswear. You can play up the contrast with sheer knee-high socks or stockings or by choosing a slip dress with lace detailing. On the oversized side of things, we recommend leaning into the lines and boxiness of a leather blazer or a more tailored, but still extra oversized, leather bomber jacket.

Over a Gauzy, Sheer 'Fit

Pugh offers a whole new silhouette courtesy of this cropped oversized leather jacket, which hits above the natural waist and gets its oversized effect from the bulk of the shoulders. The punk aesthetic pairs beautifully with feminine ruffles and gauzy patterned skirts, as Miss Flo demonstrated.

With a Maxidress

It can get — shall we say — swampy under an oversized leather jacket on a hot day, so we recommend pairing yours with a lightweight maxi dress as the weather gets warmer. Look for a soft, breathable fabric like cotton or jersey and stack on the accessories instead of the layers.

With a Hoodie and Buckle Boots

For a moto-meets-Westernwear look that still manages to sneak a bit of street style into the vibe Venn diagram, pop on an oversized leather jacket over a hoodie, leggings, and your most rugged pair of buckled boots.

With a Tulle Skirt

Calling all punk rock princesses. There are very few articles of clothing that instantly elevate a look quite like a tulle skirt. And when they simultaneously add a punk edge? Sold. We recommend keeping the elements of this oversized leather jacket look all black and adding a pop of color with a colorful statement mini bag.