When the weather turns crisp, I always find myself reaching for skirts. They’re endlessly versatile, easy to dress up or down, and flatter every stage of life. This season, I’m styling chic skirts for women over 50 that showcase how classic silhouettes, denim, slip, chiffon, and more, can transition seamlessly into fall. Whether you love a polished midi or a breezy flounce hem, these outfits are proof that skirts deserve a starring role in your wardrobe.
Here’s What You’ll Find in This Post:
- 5 chic skirt outfits for women over 50, styled for fall
- How to wear denim skirts two ways: casual and polished
- Easy pairings with tops, knits, and accessories to elevate your look
- Inspiration for both everyday style and evening occasions
Denim Midi Skirt, Two Ways to Wear It
Look One
A denim skirt is as timeless as your favorite pair of jeans. First, I styled it with a floral tie-waist popover, suede slingbacks, and chunky gold hoops, a nod to relaxed yet polished fall style.
Shop the Look
Look Two
For a second take, I paired the skirt with a classic denim shirt, black boots, and a silver conch belt for a chic double-denim moment. Both versions prove just how versatile this wardrobe staple can be.
Shop the Look
For more Denim Looks, check out my Sunday post: How to Wear Denim Over 50
Frequently Asked Questions
Chic Skirts for Women Over 50
Q: Can women over 50 still wear shorter skirts?
A. Yes, but balance is key—pair shorter hems with opaque tights or tall boots for sophistication.
Q: How do I transition skirts from summer to fall?
A. Layer with cardigans, blazers, and boots. Heavier fabrics like denim and wool work beautifully for cooler weather.
Q: What’s the most versatile skirt length?
A. A midi skirt—just below the knee or mid-calf—is universally flattering and works for both casual and dressy occasions.
Sleek & Sophisticated: The Dark Grey Skirt
The Vince double waist D-ring skirt has a sleek, modern shape that’s perfect for evenings out. Styled with a black cashmere turtleneck and suede boots, it creates an elegant monochrome look. A silver cuff bracelet and ceramic hoop earrings add subtle shine, making this outfit effortless yet striking.
Shop the Look
YouTube – More Fall Style
7 Lightweight Fall Jackets You’ll Actually Wear
🍂 Fall style made easy! In today’s video, Beth shares 7 lightweight fall jackets that are versatile, chic, and perfect for layering. From casual weekends to polished evenings out, these jackets are the pieces you’ll actually reach for again and again. Whether you’re building a capsule wardrobe or just looking to refresh your closet for the cooler months, Beth highlights timeless options that balance comfort, function, and style.
✨ Jackets featured are easy to style with jeans, dresses, and everything in between — making your fall outfits effortless and elevated.
Slip Into Style: The Navy Slip Skirt
The navy slip skirt is one of my favorite transitional pieces. Worn with a simple ivory camisole and topped with a navy cashmere cardigan, it’s understated and chic. Metallic slingbacks and a metallic handbag give the outfit a modern edge, while pearl earrings keep the look timeless.
Shop the Look
Flirty & Feminine: Kelly’s Chiffon Skirt Look
Kelly always has a knack for making petite pieces look effortless, and this chiffon skirt is no exception. She styled the Gwyneth flounce-hem skirt with a cropped cashmere tee and woven ballet flats, a pairing that feels polished yet playful. A metallic, croc-embossed handbag adds texture, making the whole look lightweight, flattering, and perfect for everything from brunch to date night.
Shop the Look
✨ Beth’s Style Wisdom
Chic Skirts for Women Over 50
1. Invest in Classics
Denim and slip skirts never go out of style.
2. Balance Your Look
Pair flowy skirts with fitted tops and structured skirts with softer knits.
3. Play With Accessories
A belt, bold earrings, or metallic shoes can completely change a skirt outfit.
4. Think Seasonal Layers
Blazers, cardigans, and boots make skirts fall-ready while keeping your look polished.
Closing Thoughts
Chic Skirts for Women Over 50
Chic skirts for women over 50 are more than just a wardrobe option—they’re a style statement. From denim midis to chiffon flounce hems, these pieces prove that skirts can be versatile, timeless, and endlessly flattering. This fall, don’t shy away from making skirts a cornerstone of your wardrobe. Whether you’re headed to brunch, an evening out, or simply want to elevate your everyday style, the right skirt makes it easy.
About The Author
LEAVE A COMMENT