How to Style Midi Skirts in Every Season for Women Over 50

You can rock a midi skirt! Because they’re a timeless wardrobe staple, always in style, offering a perfect blend of elegance and versatility, midi skirts are ideal for women over 50. They flow beautifully, provide a flattering silhouette that suits every body type, and can be styled for any occasion.

Today we’re sharing our favorite midi skirts, plus tips to style them in every season, for women over 50.

If there’s one style that transcends trends, it’s the midi skirt. Timeless and effortless, its length is the perfect in-between, a reliable option that can easily be dressed up or down and worn year-round. from The 20 Best MIDI Skirts in 2024, InStyle


Why Midi Skirts Work for Women Over 50

Midi skirts offer a combination of style, comfort, and versatility, making them a great option for women over 50. Plus, it’s not too short or too long, making it a flattering, age-appropriate option while still being fashionable.

Seasonless: Wearable year-round, midi skirts can be paired with light tops and sandals in summer or layered with tights, boots, and sweaters in colder months.

Versatile: Midi skirts come in various styles and fabrics, suitable for dressing up or down and pairing with t-shirts, blouses, sweaters, blazers, cardigans, or denim jackets.

Comfortable: Made from soft, breathable fabrics, midi skirts offer comfort and easy movement.

Classic: Their timeless appeal makes midi skirts a lasting wardrobe staple and a good investment piece.

Shop Midi Skirts for Women Over 50


How to Choose the Right Midi Skirt for Women Over 50

Let’s talk body type. Women come in all sizes; tall, petite, curvy, straight. One body is not better than the other, each of us is perfect in our own unique way. However, there are a few tricks to cheat the system. Knowing your basic shape can help you choose a skirt style that maximizes your assets. There are countless body types, we are sharing a few.

The apple shape is characterized by a larger waist and bust compared to the hips; broader shoulders, and a rounder silhouette, especially around the midsection.

A pear shaped body presents a slimmer upper body and wider hips and bottom, creating a triangle.

The hourglass shape is named for its resemblance to an hourglass, where the upper and lower halves are wide and roughly equal, while the waist is more narrow.

A rectangular shape is defined by a straight silhouette with similar width shoulders, hips, and waist, and little to no waist definition.

Choose the Right Length

A midi skirt can fall anywhere between the knee and the ankle. The most flattering lengths are a couple of inches below the knee, just above the swell of the calf, or just below the calf so that a few inches of ankle show. Essentially you want the skirt to end at the narrowest part of your leg. Length is always an issue for those of us under 5’3, as it is for our tall friends, 5’9 and up.

A few pro tips for petites, opt for a skirt that ends at the bottom of your calf muscle or just below the knee, the more leg you show the taller you look. A skirt with a slit will also help with this. Do not be afraid to get things altered. The seamstress is your friend.

We’re debunking a fashion myth at Glamour today: You don’t have to be taller than 5’4 to wear a midi skirt. Mid-length skirts are one of our favorite spring fashion trends, and they’re going to continue well into the fall. From our stylish friends at Glamour Magazine’s “Short Girl’s Guide to Wearing Midi Skirts”.

Shop Petite Midi Skirts


How to Style Your Midi Skirt in Every Season

Today we’re sharing four ways you can style your midi skirt to get the most out of this wardrobe staple. One of the great things about midi skirts is that they are versatile, you can wear the same skirt in different types of weather. It’s all about what you wear with the skirt! Sandals and a tank in summer, boots and a sweater in winter. Investing in a midi skirt will give your wardrobe choices lots of mileage.


Summer: Comfort and Breathability

For women over 50, styling a midi skirt for the summer involves choosing lightweight fabrics like cotton or linen for comfort and breathability–hot flashes + summer heat…IYKYK!

  • For a sophisticated look, choose a midi length that falls just below the knee.
  • Pair the skirt with a loose, breezy blouse or a fitted top, tucked to define your waist.
  • Accessorize with your favorite comfortable sandals and a wide-brimmed hat or sunglasses for a stylish summer touch.
  • Consider layering with a lightweight cardigan or scarf for cooler evenings or indoor settings.
  • The look below is layered with an on-trend vest (we’d leave it unbuttoned), and you could easily swap it in the evening for a linen blazer or white denim jacket.
Midi Skirts for Women Over 50 styled for summer


Fall: Layers

Fall is all about layers, the days are warm but the evenings are chilly. Pair a slip skirt with a silk blouse and layer a fun pop of leopard over for style and warmth. You could wear clogs or loafers here if the weather looked warm, for cooler temps wear boots. The perfect outfit for lunch and shopping in London.

  • wearing a column of color (all the same color) gives the illusion of height (for the shorties like Megan)
  • natural fabrics like cotton, silk, wool breath better and keep you insulated (cool or warm)
  • layers, layers, layers! You could toss a jean jacket over this for casual daytime or a black wool coat for evening.
  • boots for fall; cowboy, knee high or booties, however we also like slip on clogs and loafers for a casual look
megan's fall midi skirt


Winter: Cozy and Layered

To style a midi skirt for winter for women over 50, start with a cozy cashmere sweater (like the hoodie pictured below) or a fitted turtleneck in a seasonal color.

  • Layer with a tailored wool or quilted coat or a chic faux fur jacket for added warmth and elegance.
    • Your coat should be waist-length for a modern look, or as long as the skirt for a classic look.
  • Complete the look with knee-high boots or ankle booties and accessorize with a statement scarf and classic jewelry pieces.
  • Opt for rich textures and colors that complement the season while maintaining comfort and sophistication. And this season, you can’t go wrong with on-trend olive green.


Spring: Colorful and Fun

After the doldrums of winter have passed we’re ready to lighten things up, from color to fabric. We found a colorful cotton taffeta midi skirt that has so many colors you can pretty much wear anything with it. If we didn’t wear it with this cashmere tee shirt; a white tank with a chambray shirt tied at the waist with flat sandals would also be perfect.

  • colorful! spring is the time to bust out of the neutral zone and embrace your inner colorful self
  • like fall and winter, spring calls for layers – add a trench to this look for warmth and protection from the April showers
  • spring is also the time to lighten your lipsticks (hello pink!) and nail polish.
Megan's favorite midi skirt styled for spring


Megan’s Midi Skirt

megan wearing a navy slip/midi skirt styled for fall

SHOP MEGAN’S LOOK


Christa’s Midi Skirt

We’re all friends here, right? So, I’ll be honest—I found this assignment really challenging. If you’ve been following the blog, you’ll know I’m all about dresses—easy, effortless, one-and-done. I prefer simplicity and today’s outfit, for me, feels a bit too “fussy.” Don’t get me wrong, I love it…I’m just not sure how often I’ll actually wear it. As an alternative, I could swap out the J.Crew linen skirt for a more affordable slip skirt in almost the exact same color from Amazon. It gives the same look for a third of the price, and you won’t feel bad if it ends up sitting in your closet.

Do you ever face a “fashion challenge”? If there’s something you adore but can’t quite get to work for you, try mixing it up—maybe opt for pants instead of a skirt, or find a dress in similar colors to recreate that outfit you love.

SHOP CHRISTA’S LOOK


How Style Icons Over 50 Wear Their Midi Skirts

MEGAN: As someone that is vertically challenged (I’m 5’1), I am consistently drawn to a column of color. Racheal Ray’s look perfects the casual elegant vibe I’m looking to manifest. Lucky for me I have some variations of these pieces in my closet already. This is the perfect opportunity to remind you all to shop your closet. Find inspiration on Pinterest or google (I googled “curvy over 50 celebs in midi skirts”) and then shop your closet to recreate stylish, fun, inspired looks. If I see you out to dinner or lunch and I’m wearing this exact outfit, let’s not talk about it – mmmkay?

CHRISTA: Jennifer Garner’s classic midi skirt look from 2023 is still an inspiration! While we may not be heading to a GMA interview in New York City anytime soon (and we may not have $5,500 for a new skirt!), we can create a similar look for less that’s perfect for whatever is on your summer schedule. The black accessories styled with the pink skirt gives her look a modern vibe. And the length of her skirt is perfection!


Looking for more style inspiration?

  • Check out all the styles we’re sharing each week, plus links to shop them, here.


Save “Midi Skirts for Women Over 50” on Pinterest


We earn from your purchases made through Collective Voice affiliate links in this post, at no additional cost to you. Thank you for supporting our work.

If you’re new to Style Among Friends, don’t miss any of the good stuff. Subscribe for all the latest news and updates. When we find something we love, you’ll be the first to know!

Comments

Comments are closed.

Friends Share the Good Stuff!

When we find something we love, you'll be the first to know! Subscribe today and you'll receive our free must-have list of travel essentials.
* indicates required