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How to Find a Flattering Skirt for Every Occasion
The best fabrics, shapes and lengths for your wardrobe
9-minute read
(From left) Skirts are trendy again in a variety of lengths, fabrics and silhouettes, like the Eloquii Pleated Satin Midi Skirt in Black Onyx; Lands’ End Women’s Soft Denim A-Line Midi Skirt in Crawford Wash; Vince Camuto Women’s Pull-On A-Line Cheetah-Print Midi Skirt in Rich Black; Quince Women 100% Washable Silk Maxi Skirt in Forest Green.
AARP (Getty Images, Eloquii, Lands’ End, Macy’s, Quince)
Key takeaways
- A-line and fit-and-flare skirts are versatile and accommodate different body and leg shapes.
- Faux leather, denim and animal prints provide year-round wear, while satin and sweater-knits are for dressier or colder occasions.
- Ponte knit pencil skirts, an untucked top or sweater, and a uniform color palette can create a longer, more streamlined look.
“Are leather midi skirts practical?”
“Will a pleated skirt make me look heavier?”
“Which denim skirts are easy on curves?”
“What’s the most flattering skirt length for heavy legs?”
“Is an all-purpose tailored black skirt still a good buy?”
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Last year, many grownup women turned to their comfy wide-leg jeans and pull-on pants and said, “I’ll never wear a skirt again.” No more worries about leg discolorations, chunky calves or thick ankles. Goodbye forever to hemline dilemmas, shapewear and pantyhose. Not so fast! Skirts are trending, and everyone (even former naysayers) wants one or more. How do I know? I’m a beauty and fashion editor and personal shopper for women over 50 who has the inside track on which skirts work for every shape, size and lifestyle. Choose your best skirt now from these seven hot trends.
(From left) Ann Taylor Full Midi Skirt in Faux Leather in Black; CeCe Women’s High-Waisted A-Line Tie-Belt Midi Skirt in Java; Nine West Women’s A-Line Faux Leather Skirt in Maddie Plum.
AARP (Ann Taylor, Macy’s, Kohl’s)
1. A statement faux-leather midi
If you buy only one skirt, make it a faux leather in black or brown. It’s the perfect answer to any situation when you want to look effortlessly polished, edgy or all-out glam. A leather skirt can turn everyday tees and sweaters into an ultra-stylish outfit without the need for stilettos, a showy designer label or a major budget-blowing investment.
Regardless of your body or leg shape, opt for an A-line in a midi length, like the Nine West Women’s A-Line Faux Leather Skirt in Mineral Black ($36, kohls.com); the CeCe Women’s High-Waisted A-Line Tie-Belt Midi Skirt in Java or Rich Black ($50, macys.com); Ann Taylor Full Midi Skirt in Faux Leather in Black ($112, anntaylor.com); or Chico’s Chocolate Faux Leather Skirt in Bitter Chocolate ($105, chicos.com).
Midi is a pretty broad term. The one you want is either a short midi, which ends just below the knee at the indented spot just before the calf starts to swell, or a long midi, which ends below the curviest part of the calf. Some brands and retailers label ankle-length maxis as midis and vice versa. Let a tailor re-hem any new skirt to one of the above lengths.
Shopping tip: Deciding between a faux leather skirt and one in faux suede? Though both are trending this season, faux leather is more durable. It won’t show wear at the seat, wipes clean of spills, dirt and pet hair without residue and offers almost year-round wearability. It also has a dressier look, thanks to its subtle sheen.
(From left) Anne Klein Women’s Button-Front Denim Midi Skirt in Areis Wash; Lands’ End Women’s Soft Denim A-Line Midi Skirt in Crawford Wash; A New Day Women’s Denim Midi Skirt in Indigo.
AARP (Macy’s, Lands’ End, Target)
2. A sophisticated denim skirt
Long denim skirts are back in style as an alternative to jeans. They’re a great choice for women who want the cool look of denim without the anxiety of finding a pair of jeans that fits at the rise, belly, hips and rear. However, these are not the weathered-wash, jeans-like skirts you may have worn before. They’re a fit-and-flare shape in a medium-to-dark wash, and they can be dressed up or down.
Check out A-lines like Anne Klein Women’s Button-Front Denim Midi Skirt in Areis Wash ($89, macys.com); the Banana Republic Factory Women Denim Seamed Panel Midi Skirt in Dark Rinse ($84, bananarepublicfactory.gapfactory.com); A New Day Women’s Denim Midi Skirt in Indigo ($40, target.com); and the Gap Factory Women’s Pull-On Maxi Skirt in Medium Wash ($40, gapfactory.com) — yes, it says maxi, but it’s a midi.
Note the absence of leg slits. Vents can be useful for mobility in midis, but avoid skirts with a high slit at the front, sides or rear that make sitting, crossing your legs, climbing stairs or getting in and out of a car awkward, or that reveal way too much upper thigh.
Shopping tip: Pick up some tights to extend the wear of your denim midis for cold weather. Match them to your black or brown shoes or boots, not your blue denim skirt. Navy tights always look off-color and draw attention to themselves and your legs rather than to the skirt or your fashionable outfit.
(From left) Ann Taylor Ponte Pencil Skirt in Black; Tommy Hilfiger Ponte Pencil Midi Skirt in Midnight.
AARP (Ann Taylor, Macy’s)
3. An updated tailored black skirt
Even wardrobe basics get makeovers. Your crisp white button-down may now be oversized, your V-neck sweater might have a wider V and your blazer may be a knit. The same goes for the dependable, tailored black skirt. Once stuffy, knee-length and paired with heels and sheer hose, it’s got a new look. The straight pencil style and structure are all there, but the fabric is now a firm ponte stretch knit that resists wrinkles, and the length hovers between just below the knee and below the calf. The look can take you from desk to dinner with a change of top.
This is the one to buy if you work in an office or professional environment that calls for a serious skirt. It works with flats or low heels. While black is the ultimate multitasking color, consider brown or navy if that’s more “you.” Take a look at the Ann Taylor Ponte Pencil Skirt in Black ($90, anntaylor.com); the Tommy Hilfiger Ponte Pencil Midi Skirt in Black or Midnight ($59, macys.com); and the Banana Republic Women Ponte Pintuck Pencil Skirt in Ganache Brown, Black and Navy Blue ($120, bananarepublic.gap.com).
Shopping tip: Ponte-knit pencils now look super stylish and slimming (and professional) with an untucked sweater or tee in the same color as the skirt. Ignore the online photos that show them as tuck-ins; they’re only styled that way to display the skirt’s proportions and details.
4. A chic accordion-pleated midi
Put midis with crisp, narrow pleats on your try-on list. I find that women over 50 love this trending look but worry that pleats are “fattening” (their words, not mine!) around the belly and hips. Stop right there and take a look at the Simply Vera Vera Wang Women’s Pleated Midi Skirt in Madeira Berry, Black or Navy Water Floral ($40, kohls.com); the J.Jill Sunburst-Pleated Skirt in French Roast ($99, jjill.com); and the Nikki Lund Alessandra Pleated Midi Skirt in Black ($125, nordstrom.com). These skinny, dense pleats are more like ruching than bulky, boxy pleats. They create slim, elongating vertical lines that are only enhanced by the skirt’s fit-and-flare look and length.
Accordion pleats even come in satin, like the Eloquii Pleated Satin Midi Skirt in Black Onyx ($69, eloquii.com), for those who want a dressier version. My advice? Most of these skirts have a pull-on waist, so pair them with an untucked top to totally delete any belly concerns.
Shopping tip: Get out of your comfort zone and just try one on! Fashion rarely makes a comeback exactly the same way, including these skirts. The pleats, like leather, are the statement. They look best with a pared-down top and flats, not fancy, embellished blouses and heels. Try them with a toned-to-match pullover and ballet flats or a leather jacket and knee-high boots for a contemporary effect.
(From left) Quince Women 100% Washable Silk Maxi Skirt in Forest Green; Aqua Women’s Midi Satin Slip Skirt in Chocolate; Old Navy Women Satin A-Line Maxi Skirt in Black.
AARP (Quince, Bloomingdale’s, Old Navy)
5. A silk or satin skirt for dress-up
The silk-and-satin slip skirt saga continues. Women over 50 ask, “Can I wear them without looking ridiculous?” The truth is, some slip skirts are flimsy and do look more like something you’d wear under a dress, not instead of one. Those with a more substantial fabric and fit are an excellent choice, if you know how to wear them.
Start with a skirt like the Quince Women 100% Washable Silk Maxi Skirt in Navy, Wine Tasting Red, Forest Green, Hot Fudge, Chocolate Plum Brown or Black ($80, quince.com); the Aqua Women’s Midi Satin Slip Skirt in Black or Chocolate ($66, bloomingdales.com); the Old Navy Women Satin A-Line Maxi Skirt in Black ($16, oldnavy.gap.com); or the Nordstrom Women Bias-Cut Satin Midi Skirt in Brown Mole, Burgundy Fig, Navy Night or Black ($129, nordstrom.com). Notice a theme? They’re all rich, deep, sophisticated colors, not lingerie-ish pastels or pale ivory. And there’s no lace trim, which immediately upgrades the look. They’re also longer (two are even labeled maxis) — past the calf and closer to the ankle, which allows lighter-weight fabric to flow. These skirts may not look like much on the hanger, but you can depend on them to elevate your everyday clothes.
Shopping tip: Younger, trendy women, especially in urban areas, wear these skirts during the day. Mature women, with a few exceptions, are grabbing them for festive daytime events and evenings out. Silk and satin skirts in those deep hues are less in-your-face glitzy than sequins and metallics and glam up sweaters, boots and flats. Try them with a same-color sweater for an always-elegant monochromatic effect, or with an off-the-shoulder sweater and kitten-heel slingbacks for a cozy yet elevated after-dark look.
(From left) Croft & Barrow Women’s Elasticated Pull-On Skirt in Brown Small Cheetah; Vince Camuto Women’s Pull-On A-Line Cheetah-Print Midi Skirt in Rich Black; Loft Leopard-Print Crepe Bias Midi Skirt in Tiramisu.
AARP (Kohl’s, Macy’s, Loft)
6. An animal-print skirt
We’re seeing lots of plaid skirts right now. Resist them and pivot toward animal prints. Here’s why. At first, plaid skirts look seasonally fresh and appealing. In real life, on real bodies that are not size 2 or at least 5 foot 9, those geometric plaids maximize every pound and curve, making women look a lot wider. Instead, make your body happy and buy a skirt in a cool leopard or cheetah print, like the Croft & Barrow Women’s Elasticated Pull-On Skirt in Brown Small Cheetah ($20, kohls.com); the Anna-Kaci Women’s Leopard-Print Midi Skirt With High Waist and Flowy A-Line Fit in Brown ($40, target.com); the Loft Leopard-Print Crepe Bias Midi Skirt in Tiramisu ($50, loft.com); or the Vince Camuto Women’s Pull-On A-Line Cheetah-Print Midi Skirt in Rich Black ($35, macys.com). The neutral colors and year-round fabric make it a never-fail buy.
Shopping tip: This is your trendy belly-management skirt. Spotty leopard- and cheetah-print skirts with their small but busy allover pattern create an optical illusion that prevents the eye from focusing on bumps or bulges. Slip this on as a confidence-boosting backup anytime you feel bloated or have gained a few extra pounds. And as a bonus, “wild” patterned skirts never go out of fashion.
(From left) Inspire Chic Women’s High Elastic-Waist Knit Straight Midi Skirt in Light Camel; Donna Karan New York Women’s Straight Sweater Pull-On High-Waisted Midi Skirt in Heather Charcoal; Quince Women Mongolian Cashmere Midi Skirt in Brown.
AARP (Kohl’s, Macy’s, Quince)
7. A soft knit sweater-skirt
Knit pull-on skirts are a cozy extension of sweaters. Don’t say “No way.” For women over 50, the idea of wearing a knit skirt often conjures an image of tube skirts that’s hard to shake. But if you have no problem wearing shape-defining leggings with a sweater, a knit “column” skirt will also work. Just be sure to choose styles with a relaxed, straight-up-and-down shape; it shouldn’t be second-skin clingy.
Styles like the Inspire Chic Women’s High Elastic-Waist Knit Straight Midi Skirt in Light Camel, Gray, Coffee or Black ($36, kohls.com); the Quince Women Mongolian Cashmere Midi Skirt in Brown, Teak Brown, Oatmeal, Heather Gray or Black ($100, quince.com); the Donna Karan New York Women’s Straight Sweater Pull-On High-Waisted Midi Skirt in Heather Charcoal ($149, macys.com); and the Coldwater Creek Women’s Bird’s-Eye Sweater Skirt in Black ($100, coldwatercreek.com) have the elastic-waist comfort and leg coverage that makes chilly days pleasant. They’re the perfect alternative to the more polished ponte-knit pencil for those with a more casual lifestyle or workplace.
Shopping tip: If your weight tends to fluctuate during the year, build in flexibility by shopping only for elastic-waisted skirts. They are available in every skirt trend, from knits to denim, silk-satin to ponte pencils. Increase the flattery by wearing them with matching tops to elongate, lengthen and slim your body. Some women ask why some new skirts have an elastic waist and a zipper. The answer? These are not pull-ons. The elastic waist is for extra comfort during wear, while the zipper provides on-off functionality and firm structural support for the skirt.
The key takeaways were created with the assistance of generative AI. An AARP editor reviewed and refined the content for accuracy and clarity.
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