Wondering what to wear with a leather jacket? From classic jeans and sneakers to feminine dresses, slip skirts, and tailored trousers, a leather jacket is one of the most versatile pieces in a timeless wardrobe.

I’ve owned and worn my first black leather jacket since 2014, and it remains one of my most-used layering pieces. I love the way a leather jacket adds a little edge to an outfit while still feeling classic enough to wear year after year.

Ever since I first invested in a real leather jacket I haven’t looked back at having it be a staple in my wardrobe. I have two leather jackets I wear regularly and it remains one of my favorite layering pieces to add a bit of edge to any look.

In this post, I’m sharing my favorite leather jacket outfit ideas, including what to wear with a leather jacket in fall, winter, and spring, how to style one with dresses and denim, and what to consider when investing in a quality leather jacket.

Related: The 19 Pieces In My Closet with The Best ROI

I personally prefer more sleek, timeless leather jackets. I’m not big on moto-style leather jackets or leather jackets with belts or a lot of hardware. That’s my personal preference but of course, as always, invest in something that feels true to your personal style. 

If you’re keen to find more ways to style a leather jacket or you just want to see various ways you could wear one if you decide to invest, this post should provide some good outfit inspiration.

The leather jackets you’ll see me styling in many of these photos have been in my closet for a long time. One from 2014 from Vince (this one is similar) and one from 2017 from J.McLaughlin.

Therefore, neither are available but I’ve included a widget at the bottom of this post with some current styles that I like and I think are versatile and are from brands I shop at regularly. 

What To Wear With A Leather Jacket

Sneakers

A tried and true combination. 

Leggings

If you have a more oversized leather jacket, I love the styling with leggings for a more athleisure, off-duty weekend look.

Dresses

Feminine dresses, floral dresses, midi dresses, maxi dresses – I pair so many of my favorite dresses with a leather jacket. My most worn styling of a leather jacket is likely pairing leather jackets with dresses. 

Rompers or Jumpsuits

Add a bit of edge and make your rompers and jumpsuits able to be worn more of the year by adding a leather jacket over them.

Trousers

Make trousers less business by topping a leather jacket with your favorite pair of pants.

Baseball Cap

Add a bit of athleisure to your leather jacket look by adding a baseball cap.

T-Shirt

A plain white tee is a such an iconic pairing with a timeless leather jacket. Both of these are two of my favorite capsule wardrobe items.

Turtleneck

If you want to wear your leather jacket in winter, consider adding a turtleneck underneath or a go-to cashmere sweater. In the winter, I often treat my leather jacket as a layering piece under a favorite winter coat.

Slip Skirts

If you have a cropped leather jacket that hits above your waist, consider pairing it with the slip skirts hanging in your closet, like this one. 

Slip Dresses

And of course slip dresses are iconic with leather jackets as well.

Feminine Fabrics

I love the contrast of lace or airy and light satin or silk with the more rugged leather fabric.

Read on now to see ways I have personally styled many of these items in my own leather jacket outfits over the years.

Leather Jacket Outfits

Jeans and Boots

A tried and true styling combination is a leather jacket paired with jeans (I’m wearing this pair above in size 28). You could actually swap out the boots on the above look for a slingback or a heeled mule or even a loafer. This is a classic fall leather jacket outfit for me. 

I like leather jackets paired with medium or dark denim but I also enjoy them paired with lighter jeans during transitional weather such as going from Winter to Spring.

Related: Affordable Transitional Fall Clothing

Sweater Dress

Add a bit of edge to a more simple sweater dress by topping your favorites with a leather jacket.

If you’re keen for more sweater dress styling ideas, don’t miss my guide on How To Style Sweater Dresses.

Button Down

I love the juxtaposition of a more menswear inspired button down with a leather jacket over it. My button down above is a more casual fabric from Sezane which pairs well with the leather jacket. 

To play up the feminine meets masculine elements of this outfit, I chose a very feminine shoe and bag but added a raw-hem jean.

Trousers

Trousers are so good for dressing up or dressing down and a leather jacket is the perfect pairing with black or camel or gray trousers. 

Related: How to Style Trousers

I’m also very into a leather jacket paired with a silk trouser. It’s a chic yet comfortable pairing with a leather jacket.

Maxi Dress

Mix a feminine long, maxi dress in a fabric like silk with leather for an edgy meets glam look. I love shopping Reformation’s Long Dresses like the one I’m wearing above to pair with my leather jackets year round.

Slip Skirt

Slip skirts are so versatile in their styling options but one of my all time favorite ways to style them is with a leather jacket and simple t-shirt.

Slip Dress

And, similarly, slip dresses are great when paired with leather jackets. A leather jacket adds the perfect hint of edge to a more feminine outfit like a slip dress in my opinion.

Jenni Kayne makes great, high quality slip dresses. Use code MEGHANDONO10 for 10% off your first order.

Little White Dress

I love the visual dichotomy of a black leather jacket with a little white dress that’s super feminine in its silhouette or fabric. 

Related: What to Wear in Paris at Night

Festive Feathers

Around the holidays I love to add a leather jacket over my little black dress with feathers or a fun feathered skirt; here’s a similar option. 

Sequins

Around the holidays I always love wearing sequins and I’ll often pair sequin dresses and skirts (similar here) with a leather jacket and then another coat atop that for practicality purposes. 

Turtleneck

In need of some extra warmth? In winter I love the sleek look of layering a black turtleneck underneath a leather jacket.

Or, consider a bodysuit. 

How to Choose the Right Leather Jacket

If you’re shopping for a leather jacket to invest in consider:

• real vs. faux

• lambskin vs. cowhide

• fit (cropped vs oversized)

• hardware 

• color (black vs. brown)

I do think there is a significant difference in the quality of real leather jackets vs. faux leather jackets but as everyone’s budgets are different, you may want to save up for a real leather jacket once you’ve seen you wear your faux leather jacket a lot. I personally think Nour Hammour is making the coolest leather jackets in the market right now. I’m wearing their Artiste style in a size M in this post.

If you’re looking to invest in a leather jacket, I recommend choosing a silhouette you’ll want to wear for years rather than one that feels tied to a single trend. I tend to gravitate toward streamlined styles with minimal hardware because they’re easy to pair with everything from jeans and sneakers to dresses and tailored trousers.

One of the things I love most about a leather jacket is how versatile it is throughout the year. From pairing it with dresses and sandals in spring to layering it over cozy knits in fall and winter, here are a few ways to style one leather jacket across the seasons.

Shop the post.

Below are a few leather jackets I’d consider for a timeless wardrobe, including options in different silhouettes and price ranges.

Shop Leather Jackets

 

What to Wear with Leather Jackets

 

I hope this post is helpful as you look to style a leather jacket! And if you’ve decided you’re not really into wearing a leather jacket, perhaps try another tried and true style – the bomber jacket.

You May Also Like:

• The Best Sezane Essentials.
• My Favorite and Most Worn Shoes + How I Take Care of Them.
• My Favorite Winter Coats.

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