What to Wear with a Leather Jacket

February 28, 2024

Styling Classics I wit & whimsy

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 with regularity and it remains one of my favorite layering pieces to add a bit of edge to any look. The first black leather jacket I ever bought was back in 2014 and I still own it and wear it. It is a great example of investing in quality pieces that are well made and are timeless in their style. 

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, as mentioned, have been in my closet for a long time. One from 2014 from Vince and one from 2017 from J.McLaughlin. Therefore neither of mine 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. 

Everlane Link Stich Sweater I wit & whimsy

What To Wear With A Leather Jacket


A tried and true combination. 


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


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

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.


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.


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.

Slip Skirts

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

Slip Dresses

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

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

Everlane Link Stich Sweater I wit & whimsy

Jeans and Sneakers

A tried and true styling combination is a leather jacket paired with jeans. You could actually swap out the sneakers on the above look for a slingback or a heeled mule or even a loafer.

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

Sweater Dress Styled I wit & whimsy

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.

Styling Classics I wit & whimsy

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.

Paris Seine River


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

Paris at Night Outfit

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.

Fall Dresses I wit & whimsy

Midi Dress

Of, if you’re more of a midi dress kind of gal, you can try a patterned print or a fall floral dress to mix soft and hard in your look. 

I love styling a leather jacket over the shoulder with certain pieces as well.

Holiday Outfit Ideas I wit & whimsy

Mini Dress

I love a mini dress meets leather jacket year round.

Meghan Donovan in Paris in Bash Paris Skirt and Leather Jacket Paris Outfit

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.

What to Wear in Paris at Night

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. 

Festive Feathers

Around the holidays I love to add a leather jacket over my little black dress with feathers or a fun feathered skirt. 

Saks Party Edit Outfit


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


In winter I love the sleek look of layering a black turtleneck underneath a leather jacket.

Shop Leather Jackets
What to Wear with Leather Jackets


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. Not really into wearing a leather jacket? Perhaps try another tried and true style – the bomber jacket.

I hope this post is helpful as you look to style a leather jacket! 

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comments +

  1. Leu2500 says:

    Universal Standard is an accessable size brand. They have several styles in leather jackets – motos & blazers – on sale right now.

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