Denim Skirts for Women Over 50: How to Style

Remember when denim skirts were the “it” item in the early 2000s? They quietly stepped out of the spotlight for a while, but lately, I’ve been spotting them everywhere. Apparently, they’re not just making a comeback; they’re here to stay. Whether you’ve been side-eyeing them from a distance or you’re ready to fully embrace the trend, I think they’re one of the most versatile pieces you can have in your closet.

To me, denim skirts are that perfect sweet spot between casual and put-together. I’ve been trying out different washes, lengths, and styles, and I have to say, they’re surprisingly easy to wear. Today, I’m sharing my thoughts on why a denim skirt belongs in your wardrobe (yes, even over 50!), plus plenty of ways to style one for every season.

If you’ve been on the fence about trying a denim skirt, this Denim Midi Skirt from PAIGE might just win you over. It has a soft, stretchy denim that moves with you, and the midi length keeps it classy while the front slit makes it easy to walk in. The wash is that perfect lived-in blue that goes with everything. I’m wearing a size 29, and it fits true to size, not too tight, not too loose. This skirt is a great swap for jeans when you want something just a little different.

Why Try a Denim Skirt When You’re Over 50?

A denim skirt is like the fun cousin of your favorite pair of jeans. It’s classic, comfortable, and you can dress it up or down without much effort. Heading to lunch with friends? Throw one on with a cute top. Running errands? Pair it with sneakers and a tee. Even a casual dinner out works perfectly, just swap in a blouse and boots.

They’re also seasonless. In summer, you can keep things breezy with sandals and a tank. Once the weather cools, they look amazing with tights, boots, and a chunky sweater. And the best part? A denim skirt isn’t limited by age. Whether you’re 25 or 65, it can still be a stylish, modern piece when you choose the right fit.

Choosing the Right Denim Skirt for Women Over 50

Length Matters

If you want a denim skirt that flatters without feeling frumpy, aim for knee-length or midi. A hemline that hits just above or at the knee gives you a longer, leaner look. Midi skirts are great if you want a little extra coverage or a dressier vibe. I skip anything floor-sweeping; it’s easy for that much denim to look dated.

Fit & Cut

Look for a skirt that skims over your shape instead of clinging. A-line and pencil cuts are both timeless and flattering. And trust me, a slit, front, back, or side, makes walking and sitting much easier.

Dark Wash vs. Light Wash

If versatility is your goal, go for a dark wash. It’s more polished, slimming, and works for both casual and slightly dressier outfits. Light washes are great for a laid-back summer look, but don’t have quite the same “pulled-together” effect.

Keep the Details Simple

The most elegant denim skirts are the ones without a lot of extras. Skip heavy distressing and flashy embellishments if you want a look that lasts.

One of the first things to consider when styling a denim skirt is the fit. As we age, our bodies change, and finding a skirt that flatters our figure is key. Here are a few things to look for when selecting the perfect denim skirt.

The Casual Everyday Look

For those days when you’re running errands or meeting friends for coffee, you want an easy and effortless outfit. Here’s how to style a denim skirt for a casual, chic look:

• Pair with a Simple T-shirt or Sweater: A classic white or striped T-shirt always looks great with a denim skirt. In cooler weather, swap the tee for a lightweight sweater. Choose neutral colors like white, beige, or navy for a clean and classic look.
• Add a Cardigan or Denim Jacket: Layering is your best friend, especially as temperatures fluctuate throughout the day. A cozy cardigan or even a lightweight denim jacket (yes, double denim can work!) adds warmth and style without being too heavy.
• Footwear Options: Sneakers are a fantastic option for a casual look. White or neutral-toned sneakers keep the outfit looking fresh and youthful. If you prefer something a little more polished, a pair of flats or low-heeled ankle boots will do the trick.
• Accessorize with a Crossbody Bag: For an everyday look, a small crossbody bag is both practical and stylish, but you could also grab your usual tote bag!

The Elevated Evening Look

If you’re heading out for a casual dinner or want to dress up a bit for a special occasion, a denim skirt can still be your go-to piece. Here’s how to elevate your look:

• Choose a Blouse with Elegant Detailing: Swap your casual t-shirt for a blouse with interesting details like ruffles, lace, or bell sleeves. You can also go with a top with an elegant print to add a little interest!
• Blazers Add Instant Sophistication: If you want to give your outfit a more polished vibe, throw on a blazer. A structured jacket instantly elevates any look. You can see some of my favorite blazers here.
• Step Into Heels or Heeled Boots: If I’m heading out for a date night, I’m usually grabbing my heels. Block heels or heeled ankle boots are both comfortable and stylish. Just don’t pick a heel that’s too formal for a denim skirt!
• Accessorize with Statement Jewelry: Add a pair of statement earrings or a chunky necklace. Don’t overdo it—one or two bold accessories are all you need to complete the outfit.

The Transitional Fall/Winter Look

As the temperatures drop, your denim skirt can easily transition into your fall and winter wardrobe. I styled a Lightweight Denim Fly Front Midi Skirt with this No Iron™ Long-Sleeved Floral Shirt, a Knee High Boots, and a Suede Belt, and I love how it turned out. Here are some more tips on how to style a denim skirt for cooler weather:

• Pair with a Knit Sweater: A chunky knit sweater can add cozy texture to your outfit while keeping things cute and stylish. Turtlenecks are a great way to keep warm while looking put-together.
• Add Tights or Leggings for Warmth: When it gets chilly, throw on a pair of opaque tights or leggings under your skirt to keep your legs from freezing. Black tights are a safe, slimming choice that pairs well with any wash of denim, but you can always go with nude!
• Complete the Look with Boots: Tall boots are my shoe of choice for fall and winter outfits. Knee-high or over-the-knee boots keep you warm and add a touch of sophistication. Ankle boots will also work well with your denim skirts, especially when paired with tights.

Outfit Inspirations Wearing Denim Skirts

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