The Best Skirts for Women Over 50 in 2024

3. Deal with the waist and belly issue.

Skirts are not just about hemlines. They’re also about any weight issues and belly bulge concerns. While skirts do eliminate some of the fit problems of pants and jeans, especially at the thighs and rear, they’re not entirely off the fit hook. If you like the idea of full roomy midi skirts and have natural waist definition or some sense of an indent at the waist, you have two options. Choose an A-line style with a defined waistband that features a belt (or loops so you can add your own) like the Worthington Women’s Mid Rise Midi Pleated Skirt in Multi Palm ($48, jcpenney.com), or opt for a pull-on A-line skirt like the Chico’s Linen A-Line Midi Skirt in Alabaster ($80, chicos.com) that features a wide, flat elastic band at the top. Both gracefully conceal a tummy, emphasize your curves and work with tucked-in or semi-tucked tops and sweaters.

On the other hand, if you lack any real waist and/or have a belly concern, you also have two options. Choose easy-fit pull-on midis like the Old Navy High-Waisted Satin Midi Slip Skirt in Mocha Taffy ($28, oldnavy.gap.com) that are cut flat and smooth across the belly and hips or those like the J. Crew Factory Wrap Midi Skirt in Azalea Belvedere Red ($45, factory.jcrew.com) that feature subtle draping across the front for even more extra help. The smooth skirt makes an ideal neat base for untucked tops and layers (for example a tank and V-neck sweater), while the draped front makes a semi-tuck and tucked-in tops possible.

Super skirt tip: Regardless of your waist situation, if your weight tends to fluctuate up and down during the year, build in flexibility by sticking to elastic waist skirts and match skirt color and top to elongate, lengthen and slim. Or let skirts with busy prints create an optical illusion that prevents the eye from focusing on bumps and bulges.

(Left to right) Everlane The Knit Pleated Skirt in Black; H&M Pleated Skirt in Burgundy; Marcella Vesey Pencil Skirt in Black

Photo Collage: AARP; (Source: Everlane; H&M; Nordstrom)

4. Try a new-again skirt style.

Get out of your comfort zone! Some trending styles like slip skirts and pleated skirts may get an “I wore that back in the ’70s (’80s or ’90s)” response. I get it. Yes, skirt trends do get recycled, and women over 50 may have worn these styles before. However, nothing comes back the same way, including these skirts. Bias cut satin slip skirts so popular in the ’90s were essentially evening-only pieces that were worn with romantic blouses and heels. Fast-forward to 2024 and this time around slip skirts like the J. Crew Gwyneth Slip Skirt in Deep Chocolate or Navy or Black ($90, or $63 with coupon, jcrew.com) have those stretchy waistbands and an expanded day-to-night agenda. In fact, they pair perfectly with cozy sweaters and ballet flats. Pleated skirts like the H&M Pleated Skirt in Black or Burgundy ($40, hm.com/en_us/) and the Everlane The Knit Pleated Skirt in Black ($178, everlane.com) with their preppy vibe look modern in midi lengths and slimmer knife or accordion pleats. They have a sophisticated, graceful look that’s stylish with ballet flats, low slingback heels or a pair of knee-high boots. If you’re wondering whatever happened to pencil skirts — there are plenty of denim pencils and pull-on ponte versions like the Marcella Vesey Pencil Skirt in Black ($114, nordstrom.com) in midi length that take the stuffiness out of office wear. And let’s not forget the glitzy evening version of pencil skirts! See tip No. 6.

5. Build up your casual skirt category.

Skirts have always had a more dressed-up rep. However, denim and tiered skirts — two more born in the ’70s and revived in the ’90s styles — have become current dress-casual favorites. Not surprisingly, both look great with flats, sneakers, sandals. They’re an ideal alternative to jeans and leggings and layer up and down easily with tees, sweatshirts and sweaters. And yes, you can slip on a pair of opaque tights and boots too when the weather cools down. Which one is you? A denim skirt like the Lauren Ralph Lauren Belted Denim Midi Skirt in Stormee Wash ($145, bloomingdales.com) offers more structure and a cool edgy look; a tiered skirt like the Chelsea & Theodore Pull-On Woven Pleated Midi Skirt in Black ($32, kohls.com) is softer with an elastic waist and a boho feeling. For extra polish and a slim, sleek effect all you need to do is tone your tops to the skirts (a great mantra I keep repeating but it does work for all). Try a navy sweater with a jean skirt, a black turtleneck with a black tiered skirt.

Super skirt tip: Avoid jean skirts that feature high slits front and center. Designed for a sexy aesthetic, they reveal way too much upper thigh and are hard to sit in, let alone cross your legs. Instead look for A-line styles with a side slit like the Levi’s Women’s Side Slit Skirt - Artist Divided ($50, target.com) or denim pencils that feature a modified slit at the back or front just enough for ease and mobility.

(Left to right) Alex Evenings Women’s Tea-Length A-Line Ball Skirt in Black; VICI Collection Animal Print Satin Maxi Skirt in Tan/Black; Eloquii Maxi Sequin Skirt in Silver Black

Photo Collage: AARP; (Source: Macy's; Nordstrom; Eloquii)

6. Grab a party skirt.

Your “good” black pants, a silk blouse and statement earrings are one option for a party outfit; so is the go-anywhere dress with a change of shoes. There’s a third solution, and that’s what I call “the superstar skirt.” It’s all in the fabric. Whether sequins like the Anna-Kaci Women’s Sparkly Sequin Cocktail Midi Skirt in Black ($40, target.com) and the Eloquii Maxi Sequin Skirt in Silver Black ($110, eloquii.com), satin like the VICI Collection Animal Print Satin Maxi Skirt in Tan/Black ($68, nordstrom.com), metallic or tulle, this is the slip-on-and-go skirt that elevates any basic black top or bodysuit or any white shirt to festive levels. Maybe it’s the black sequin skirt you wear with a black turtleneck to a cocktail party; the shimmery maxi you team up with an off-the-shoulder sweater; the satin slip skirt you wear with a crisp white shirt; and the black A-line ball skirt like the Alex Evenings Women’s Tea-Length A-Line Ball Skirt in Black ($99, macys.com) that makes an entrance and lets you eat dessert! These skirts may not look like much on the hanger, but you can depend on them to never fail to make an entrance … and a spectacular exit.