The Most Stylish Skirts for All Ages
The trusty skirt can often get overlooked in your closet, giving way to floral frocks and staple jeans instead. But turn your attention to its many attributes—sophisticated, flattering, and versatile—and you’ll see just how much potential a simple skirt can add to your world of sartorial possibilities.
It’s also important to add that a great skirt defies time—perfect for all ages. The trick is finding one in a timeless silhouette (think a wrap skirt or A-line), made of a quality fabric (no heavy denim distressing or overpowering embellishments), and hits an appropriate length, falling easily on the body—a midi skirt is one of our favorites that is universally flattering for all ages and figures. (And yes, you can wear a miniskirt over 40.) Here’s the fun part: You can style your skirt to reflect your personality. Pair a silk midi skirt with this season’s must-have sneakers or opt for a leopard-print A-line skirt that skims over a chic pair of knee-high boots when fall arrives. The options are endless.
Scroll below for our must-have timeless skirts—perfect for all ages.
Contrasting buttons lend a modern touch to this sophisticated midi.Available in sizes 0 to 14.
Silky slip skirts are timeless and can be paired with everything from barely there sandals to sneakers.Available in size S.
A wrap skirt is universally flattering.Available in sizes DK34 to DK42.
Leopard prints are having a moment this summer and have no signs of slowing down for fall. Time to invest in this ageless print.Available in sizes FR34 to FR46.
Asymmetric pleats are a perennial fashion favorite.Available in sizes 0 to 14.
This classic A-line silhouette is worth the investment. Thank you, Gucci. Available in sizes 36 to 48.
A polka-dot print defies age.Available in sizes 2 to 12.
Tweed fabric adds a grown-up touch to this perfect-length mini.Available in sizes 4 to 14.
Your denim will last you through your years if you keep the silhouette fuss-free. We can’t wait to style this with a turtleneck and knee-high boots come winter.Available in sizes 24 to 32.
An asymmetric design looks chic with pointed-toe kitten heels.Available in sizes DK34 to DK42.
Say yes to a striking floral print.Available in sizes 0 to 18.
Wear this long-lasting print from work to weekend.Available in sizes XS to M.
A ditsy floral print exudes flirty French charm.Available in sizes XS to L.
Up next, all the midi dresses worth buying are under $100.
Judith Jones is the senior fashion market editor at Who What Wear who specializes in shopping content and trend stories with high-affiliate impact. She shares the coolest, most desirable fashion market finds and brands for every budget. Previous to working in fashion, Judith worked as a TV host on the PBS travel show Globe Trekker (airing on Netflix and Amazon Prime) sharing her passion for travel and culture.
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