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Ladylike leather—is it even possible? The typically tough-girl material can seem intimidating, but with the right pieces and silhouettes, you can look beautifully feminine and cool. Perfect for autumn and winter, leather is a rich, luxe material that will instantly add an edge to your outfit—and a pretty one at that!

With the help of stylist and blogger Brynn Watkins of Being Elliott who loves helping women celebrate their unique style, we have four gorgeous and totally wearable leather looks to inspire your fall wardrobe.

And a special thanks to the winners of our real women model call-out, Katrina and Kelsey. How stunning are they?


Katrina Bello, Singer/Songwriter


"Leopard is a closet staple. This number has the perfect mix of leopard and leather. I adore this pairing with comfy evergreen leather pants from Zara." -Brynn

Leather pants don't have to mean skintight. The trendy, slouchy trouser look easily translates with leather and looks super modern. Wear at your natural waist and keep the rest of the outfit simple. An animal-print top with leather baseball sleeves (very in right now) and leather pants make quite the statement on their own. High heels add a sophisticated feminine touch.


Top, H&M / Pants, Zara / Shoes, Shoedazzle / Necklaces, Ross (similar) / Watch: model's own



Kelsey Marie Paff, aspiring children's book writer

"When in doubt, layer. A pleated leather midi skirt is the anchor to this stylish outfit. Add a black leather top from H&M for monochrome balance. Finish off this look by throwing on an army green jacket with leather sleeves for a fun evening on the coolest of nights." -Brynn

We can't get enough of the flattering midi skirt, especially when it comes in the ever-feminine and flouncy accordion pleat. Wear the longer skirt at a higher waistline to lengthen the leg and tuck in your top. If you're going to be adventurous and wear leather on leather, stick to all-black—it's always chic and you can barely tell you're wearing it head-to-toe.


Jacket, H&M (similar) / Shirt, H&M (similar) / Skirt: Zara / Shoes: Nine West (similar)



"You can't go wrong with stripes. Both classic and functional, this fashion-forward striped dress transitions from work to play with ease. Pop on a leather vest, like this one from Free People, to top off the look with a vintage flare." -Brynn

A striped midi dress is a year-round staple. To help break up the long silhouette of the midi-length, a cropped vest adds structure and draws the eye up towards your face. It's the perfect combo for any outfit. Plus, adding classic black pumps brings an air of refinement.




 / Vest, 

Free People

 / Shoes: 

Ivanka Trump



"Colored leather is a bold statement for an outfit and needs balance. This maroon pencil skirt sets wonderfully against this oatmeal-hued fisherman sweater. Add a chic pair of booties from J.Crew to finish off this ideal look for fall."  -Brynn 

Chunky knits are a mainstay for the cold, blustery days ahead. Good news: They work beyond just a movie night curled up on your couch. Mixing dressy and casual is super chic and easy. Keep it simple and balance the color, as Brynn mentioned, as well as fit (a loose piece with a form-fitting piece). The fitted pencil skirt is dressy, while the ankle booties keep the look modern.


Sweater, H&M / Skirt, Zara / Shoes, J.Crew (similar