Chic Fall Outfits with Leather Jackets for Women Over 50
A leather jacket is something I don’t mind splurging on because it always earns its keep. It’s a great layering piece I reach for all the time—whether I want to stay warm, add a little texture, or give my outfit just a touch of cool. It’s versatile, timeless, and always looks fabulous.
If you’ve ever bought a leather jacket and then found yourself standing in front of the mirror thinking, “Okay, now what?”—you’re not alone. That’s why I created these style collages.
Each look starts with a chic, new fall leather jacket and builds a whole outfit using flattering, modern pieces that work beautifully on women over 50. These outfit collages are a fun way to “Tweak Your Chic” and step into Fall feeling confident and pulled together.
Take a look at how I styled the latest fall leather jackets…
brown leather jacket | jeans | ribbed top | sling backs | bag | earrings
1. Elegant and Effortless: Chocolate Leather Jacket with Jeans
Some leather jackets feel a little too tough and masculine for my style. That’s why I’m crushing on this super-feminine peplum leather jacket—a new silhouette for Fall. Chocolate brown is also a popular trend this season. I love it because it’s softer and warmer than black and especially flattering on mature women. The cream tank also softens the look, and straight-leg jeans keep it easy and modern. I finished off this look with pointed-toe slingbacks and gold teardrop earrings—polished, pretty, and so chic for Fall.
moto jacket | skirt | turtleneck | earrings | boots | blue purse
2. Soft Neutrals with a Twist: Tan Leather Bomber and Flowing Skirt
It’s pretty standard to see a leather jacket paired with jeans—or sometimes a dress—but it feels special when it’s styled with a skirt. And this one? It’s beautiful. I love the soft textures and creamy neutrals in this outfit. The caramel leather bomber brings a sleek, modern edge to the flowy pleated skirt, while that pop of blue in the bag keeps the look feeling fresh and fashion-forward. It’s the kind of outfit that feels just right for fall travel or a stylish daytime event.
black leather jacket | jeans | black bag | booties | white sweater | earrings
3. Polished and Parisian: Black Leather Jacket with Gold Buttons
This might be my favorite of the bunch. There’s something so chic about a black leather lady jacket with classy gold buttons—especially when paired with dark denim wide leg jeans and a soft ivory knit. The brown suede booties and bucket bag add a touch of warmth. This outfit is perfect for city shopping, days out, or dinner with friends.
black moto jacket | khaki jeans | black crossbody | black booties | black tank | earrings
4. Cool and Confident: Moto Jacket with Wide-Leg Jeans
If you are a rebel at heart, this one’s for you. This black moto-style jacket with a classic rock ‘n’ roll vibe feels modern and chic when paired with a sleeveless black knit top and these fabulous olive-wash jeans. I love these cool new square-toe booties that seem to be everywhere this fall, and the new barrel bag style is one of my favorites. Add some chunky gold, mirror-polished huggies to tie the outfit together, and you’re all set to look like a cool girl, even when you’re running errands.
Over to You to Decide!
Which one of these looks speaks to you? Let me know in the comments—or tag me if you re-create one on Instagram. And if you’re still on the hunt for the perfect jacket, check out my guide to the best leather jacket styles for women over 50 .
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