There’s something undeniably cool about a well-worn leather jacket. It’s the kind of piece that gets better with age—and I think that’s something we can all relate to.
If you’ve been on social media lately, you’ve probably seen the oversized leather jacket everywhere. They’re calling it “cool girl chic”—that effortlessly polished, borrowed-from-the-boys aesthetic that looks like you didn’t try too hard (even when you did). And here’s the thing: this trend isn’t just for twenty-somethings. It’s for us too.
Whether you prefer an oversized bomber or a classic moto jacket, leather is one of the most versatile pieces in your closet. Today I’m sharing exactly what to wear with a leather jacket—from casual weekend looks to dressed-up options—so you can make the most of this wardrobe workhorse.
Two Leather Jacket Styles Every Woman Over 50 Should Own
Before we get into outfit ideas, let’s talk about the two leather jacket silhouettes that work hardest in a grown-up wardrobe.
The Oversized Bomber
This is the “cool girl chic” jacket of the moment. The relaxed, borrowed-from-the-boys silhouette feels modern and effortless. Look for one that hits at or below the hip with a bit of room through the shoulders and sleeves. Vintage or thrifted bombers often have the best lived-in patina—something you can’t buy new.
The Moto Jacket
The classic. A moto jacket (also called a biker jacket) has a more fitted silhouette with an asymmetrical zip closure and usually some hardware details. It’s edgier than a bomber but equally versatile. If you only own one leather jacket, this is probably it.
Both styles work beautifully for women over 50—the key is choosing the right one for your outfit and styling it with intention.
If you love outfit formulas as much as I do, you’ll want to check out my Fall Outfit Formulas for Women Over 50—I break down how a leather jacket fits into several of my go-to combinations.
Oversized Bomber Jacket Outfit Ideas
This leather bomber from Banana Republic caught my eye immediately. The oversized silhouette felt modern without being over-the-top, which is exactly what I look for at this stage of life. I styled it two completely different ways—one casual and one more polished—to show just how versatile an oversized leather jacket can be.
If there’s one jacket having a moment this year, it’s the oversized leather bomber. But this isn’t about chasing trends. It’s about choosing a piece with presence—one that instantly elevates simple staples like jeans and a white tee, or adds contrast to softer, more feminine pieces. When done right, an oversized leather jacket brings confidence, ease, and that effortless “cool girl” energy at any age.
Outfit One: The Casual Weekend Look With Jeans
For an effortless weekend outfit, I paired the leather bomber with cuffed straight-leg jeans, a black ribbed turtleneck, and pointed-toe black boots.
The deep cuff on these jeans adds visual interest and keeps the proportions balanced with the jacket’s boxy shape. When you’re working with an oversized silhouette on top, a cleaner line on the bottom prevents the outfit from looking sloppy.
Beth’s Style Tips for This Look:
- Tuck in your turtleneck. This creates definition at the waist, which is essential when wearing an oversized jacket. Without that waist definition, you risk looking shapeless.
- Add a belt. Even if it’s partially hidden, a black belt with gold hardware ties everything together and echoes any hardware details on your jacket.
- Keep accessories simple. Gold hoop earrings finish the look without competing with the jacket. Let the leather be the star.
- Choose the right boots. A pointed toe and a bit of heel elevate jeans instantly. Ankle boots or knee-high boots both work beautifully here.
This formula—leather jacket, turtleneck, great jeans, and boots—is my go-to when I want to look pulled together but not overdone. Perfect for Saturday errands, lunch with friends, or a casual dinner out.
If you’re looking for more ways to style your denim this season, don’t miss my Fall Denim Trends for Women Over 50.
Outfit Two: Dressed Up With a Tartan Pencil Skirt
Here’s where things get interesting. That same leather jacket takes on an entirely different personality when paired with a tartan pencil skirt and suede heeled boots.
The unexpected combination of an edgy leather jacket with a ladylike pencil skirt creates that mix of classic and cool that defines great personal style. It’s polished enough for a holiday dinner or drinks with friends, but it still feels authentically me.
This tartan pencil skirt is giving all the Ralph Lauren heritage vibes I love. If that aesthetic speaks to you, you’ll enjoy my post on What to Wear to Your Ralph Lauren Christmas.
Beth’s Style Tips for This Look:
- Let the skirt do the talking. The plaid brings in rich jewel tones—deep red, navy, and touches of gold—that feel festive without being over the top. Because the skirt has so much pattern and color, keep everything else simple.
- Stick with the same base layer. I’m wearing the same black turtleneck from the casual outfit. This proves you don’t need a closet full of different tops—one great black turtleneck works for multiple occasions.
- Match your leather. Black bag, black boots, black jacket. When you’re mixing textures (leather, suede, wool plaid), keeping the colors cohesive prevents the outfit from looking busy.
- Add sunglasses for polish. Even in winter, a great pair of sunglasses elevates any outfit and adds a touch of glamour.
- Choose heeled boots over flats. The height balances the midi length of the skirt and keeps the silhouette elongated and elegant.
Moto Jacket Outfit Ideas
A moto jacket has a slightly different energy than a bomber—it’s more structured, a bit edgier, and works beautifully for both casual and polished looks. Here are my favorite ways to wear one:
With a White Tee and Jeans
This is the ultimate cool girl uniform, and it works at any age. A crisp white tee tucked into high-waisted straight-leg jeans, topped with a black moto jacket. Add gold hoops and ankle boots, and you’re done. Simple, timeless, effortlessly chic.
Beth’s Style Tip: The white tee is doing heavy lifting here, so make sure it’s a good one—slightly fitted, quality cotton, no logos. This isn’t the place for a baggy undershirt.
With a Dress
Throw a moto jacket over a floral or solid dress, and you’ve instantly taken a feminine look and given it edge. This combination works for everything from brunch to a casual wedding. Finish with ankle boots or ballet flats, depending on the vibe you want.
With Trousers and a Silk Blouse
For a work-to-dinner look, layer a moto jacket over tailored trousers and a tucked-in silk blouse. The leather adds personality to an otherwise classic outfit. Swap the blouse for a simple black turtleneck, and you’ve got an evening look.
With Leggings (Yes, Really)
A structured moto jacket is one of the best toppers for leggings because it provides shape and polish. Pair with a tunic-length sweater underneath and ankle boots. This is my go-to errand-running outfit when I want to feel put together without too much effort.
For more legging styling ideas, check out my post How to Wear Leggings After 50.
How to Choose the Right Leather Jacket Over 50
Not all leather jackets are created equal, and finding one that flatters your figure makes all the difference. Here’s what to look for:
Fit matters more than style. Whether you choose a bomber, moto, or blazer style, make sure it fits well in the shoulders. An oversized fit is intentional and chic; a jacket that’s simply too big looks sloppy.
Consider the length. Hip-length jackets are the most versatile. They work with jeans, skirts, and dresses equally well.
Skip excessive hardware. Too many zippers, studs, or buckles can look costumey. Classic, clean lines are more elegant and timeless.
Think beyond black. While black is classic, it can be harsh against some skin tones as we get older. Brown, cognac, burgundy, and navy are all beautiful alternatives that may be more flattering.
Quality over quantity. A well-made leather jacket is an investment piece. Whether you choose genuine leather or high-quality faux, look for smooth texture, clean stitching, and substantial weight.
Not all leather jackets are created equal, and finding one that flatters your figure makes all the difference. Here’s what to look for:
Shop the Look: Amazon Dupes
You don’t need to spend a fortune to get this look. Here are some affordable alternatives I’ve found on Amazon:
Oversized Leather Bomber Jackets:
- AUTOMET Women’s Oversized Faux Leather Jacket – This best-seller has the same relaxed bomber silhouette at a fraction of the price. Available in black and brown.
- Sampeel Oversized Faux Leather Bomber Jacket – Great reviews and a classic fit that works for all body types.
- PRETTYGARDEN Faux Leather Bomber Jacket – Another highly-rated option with the oversized fit and clean lines.
- Steve Madden Faux Leather Oversized Bomber – A recognizable brand name with quality construction.
Moto Jackets:
- BLANKNYC Faux Leather Moto Jacket – A cult favorite with the classic asymmetrical zip and fitted silhouette. Runs true to size.
- Levi’s Faux Leather Moto Jacket – Quality construction from a trusted brand, available in multiple colors.
- AUTOMET Women’s Faux Leather Moto Jacket – Budget-friendly option with great reviews.
- Lock and Love Faux Leather Biker Jacket – Highly rated with a slightly cropped fit that works well with high-waisted jeans.
Tartan Pencil Skirts:
- Wool Plaid Pencil Skirt with Back Slit – High-waisted with a midi length, perfect for recreating this look.
- RANPHEE Tartan Midi Skirt – Tummy control panel and elastic waist for comfort.
- High Waisted Tweed Bodycon Tartan Skirt – Classic plaid pattern in multiple colorways.
Black Ribbed Turtleneck:
Look for a fitted ribbed turtleneck in a stretchy fabric. Amazon Essentials and ANRABESS both make affordable options.
Frequently Asked Questions
What is the “cool girl chic” leather jacket trend?
Cool girl chic is the effortlessly polished aesthetic built around an oversized leather jacket—think borrowed-from-the-boys vibes with minimal styling. The look is relaxed but intentional, pairing the jacket with basics like turtlenecks, great jeans, and simple accessories. It’s less “trying hard” and more “I woke up like this”—and it works beautifully for women over 50.
Can women over 50 wear leather jackets?
Absolutely. Leather jackets are timeless and look chic at any age. The key is choosing a flattering fit and styling it appropriately for the occasion. A well-chosen leather jacket adds polish and edge to any outfit without trying too hard.
What do you wear with a leather jacket?
The beauty of a leather jacket is its versatility. Classic pairings include jeans and a white tee, a midi dress, trousers with a silk blouse, or even leggings with a tunic sweater. For a dressier look, try a leather jacket over a pencil skirt and turtleneck. The key is balancing the jacket’s edge with the rest of your outfit.
What style leather jacket is most flattering for mature women?
Classic silhouettes work best. Look for bomber jackets, simple moto styles, or leather blazers with clean lines and minimal hardware. Avoid anything too cropped or with excessive embellishments. Hip-length cuts are universally flattering.
Is it better to buy real leather or faux leather?
Both have advantages. Genuine leather lasts longer, develops beautiful patina over time, and molds to your body. High-quality faux leather is more affordable, often easier to care for, and a good ethical choice. Either can look fantastic—focus on quality construction regardless of material.
What colors work best for leather jackets on women over 50?
While black is classic, don’t be afraid to try softer alternatives. Tan, cognac, burgundy, navy, and deep green can be more flattering than harsh black, especially if you have lighter or more muted coloring. These colors also pair beautifully with more items in your wardrobe.
How do I style a leather jacket without looking like my daughter?
Keep the rest of your outfit simple and let the jacket be the statement piece. Pair it with basics—a great turtleneck, well-fitting jeans, or a simple dress. Avoid competing statement pieces and keep accessories minimal. The goal is effortless, not costume.
Can I wear a leather jacket with a skirt?
Yes! This is one of my favorite combinations. A leather jacket with a pencil skirt or midi skirt creates a beautiful contrast between edgy and feminine. The key is keeping the color palette cohesive and choosing a skirt length that balances the jacket’s proportions.
The Takeaway
If you have a leather jacket that’s been sitting in your closet, I hope this inspires you to pull it out and experiment. The beauty of a great jacket is its versatility—it goes casual with a white tee and jeans, dressy with a pencil skirt, or somewhere in between with a midi dress.
And don’t be afraid of vintage or thrifted leather jackets. That lived-in patina? It’s not something you can buy new. It’s earned.
Watch the Video
Want to see these outfits in action? Watch my YouTube video where I share even more styling tips for women over 50.
What’s your favorite way to style a leather jacket? I’d love to hear in the comments!
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