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Master Fall 2022 Fashion With These 5 Essentials for Women Over 50

How to level up your style with just a few trendy options.

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photo collage of fall clothing items
Ethel Staff
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Like a fading romance, we can’t bring ourselves to totally break up with the comfortable pandemic sweatpants and baggy T-shirts from the past three winters. We still crave their soft touch and how forgiving they are, even if we’ve tired of their blandness and predictability. In some ways, though, that, too, was part of their appeal.

Fond memories all, but we have to move on and lift our sights higher. Our rebound relationship has brought us to another place of familiarity: our five easy pieces. These wardrobe essentials retain the comfort that sustained us for so long, but they have more game in their playbooks.

Check out our suggestions to easily level up your style with trendier options from the fall and winter lookbook.


In many closets, sweatpants finally have been replaced by more fitted and elevated joggers. If you’re slow to turn that corner, fall offers an ideal opportunity for an upgrade. Some options include Old Navy’s Mid-Rise Breath On Jogger Pants ($35 at oldnavy.com) and the expanded color palette of Vuori’s Performance Jogger ($94 at vuoriclothing.com). To add extra warmth and luxury, you can pull on Talbots' new sister brand Haven Well Within's Cotton Cashmere Joggers or Cashmere Honeycomb Joggers.

Leveling up

Brands across the spectrum are delivering the comfort factor with a strong one-two punch of stretch fabrications and forgiving cuts. For pants, that means options like Ann Taylor’s pull-on Easy Ankle Pant ($89-$98 at anntaylor.com) in black or olive knit with an elasticized waistband in back. At Banana Republic, the Tapered Cargo Pant ($120 at bananarepublic.com) scores big points for comfort, pockets and its range of colors. (Online shopper hack: Banana Republic Factory often offers lower-priced versions of its parent brand’s styles, so click over for a look at bananarepublicfactory.com.)

Chelsea boots

If you haven’t tapped into the short boot trend yet, the Chelsea style is the place to start. With its low-slung silhouette, elasticized gusset and rounded toe, it is all about comfort. I purchased a Franco Sarto pair last fall for a trip to Chicago. Even on the days we walked five miles around the city, my feet didn’t complain. Although my particular model is no longer available, a nearly identical twin is the Franco Marcus Bootie ($160 at francosarto.com) in black leather. Another similar style that earns high marks for comfort is the Cole Haan Chelsea Boot ($170 at amazon.com).

Leveling up

From the traditional Chelsea, you can go either direction to make a next-level statement. A lug sole amplifies its utilitarian appeal in the Audrick Chelsea Boots from Doc Martens ($200 at bloomingdales.com), or Journee’s vegan-leather offering, the Ivette Chelsea Boot ($70 at dsw.com).

The denim jacket

Toss a jean jacket over anything from a white silk blouse to a black mock turtleneck, and you’ve got easy, instant cool. Most of us have a favorite denim jacket in our closet, but if you’re looking for an update, the freshest styles hit at the waistline. For fall, consider a dark wash in Old Navy’s Classic Jean Jacket ($40) or a medium wash in the Distressed Classic style ($40 at oldnavy.com). Levi’s Original Trucker Jacket ($90 at levi.com) hits all the right notes too.

Leveling up

If you’ve already got a denim jacket and are looking to take your outerwear options up a notch, two familiar styles are worth a look: the bomber jacket and the moto jacket. With its ribbed band, the bomber is the more forgiving style and accommodates many shapes. Depending on your budget and personal preferences, you can choose between a leather version like Treasure & Bond’s Leather Bomber Jacket ($230) or a leather lookalike such as BLANKNYC’s Faux Leather Bomber Jacket ($98, both at nordstrom.com). Biker chic was a prominent trend on the fall runways, making the moto jacket a high-visibility option complete with zippers, snaps and attitude. You can find the Leather Moto Jacket in black at Banana Republic Factory ($350). Levi’s Faux Leather Belted Motorcycle Jacket comes in standard and plus sizes as well as black and more than 25 additional colors ($80-$105 at amazon.com).

Something plaid

As the temperatures dip toward the 60s, signaling fall in Florida, where I live, I begin eyeing my plaid flannel shirts. I love their colors, their softness and how easily they layer over everything from T-shirts to sweaterdresses. Despite my propensity for plaids, I waited — while others rushed — to embrace the plaid shacket last fall, leaving me without the trendy part shirt, part jacket. Happily, the utilitarian shacket is making a return engagement this fall in even more colors and cuts. Thread & Supply delivers its Plaid Flannel Shacket in rose or gray ($49 at nordstrom.com[RJ(1] ), while Cotton On’s The Shacket Jacket arrives in a rich smoked paprika or elegant camel ($70 at macys.com).

Leveling up

With plaids storming the fashion runways from Paris to New York, it will be easy to find the distinctive pattern in next-level offerings from edgy to elegant. In that sweet spot of accessible, plaid turns up in mainstream styles like a puff-sleeve top ($65) or swing shirtdress ($90, both at loft.com) that are ideal for a day spent running errands. Pair with tights and booties, and you’re good to go.


A longtime fall favorite, the cardigan adds an extra hug of warmth that makes it an ideal transitional partner. If you’re looking to add to your collection, the standouts this season are loaded with texture and color. The Stitchy Cardigan ($65 at loft.com) delivers on its name with nubby texture, while the swirling jacquard print of Jkerther’s Y2K Print Cardigan ($34 at amazon.com) capitalizes on the color angle, both hitting at the waist. For something longer, look to the Madewell Bobble Cardigan ($118 at nordstrom.com) or the Montana Cable Cardi ($148 at freepeople.com), each available in a range of hues.

Leveling up

Try on the ruana, which has as many uses as it does names, including “that wrap thing.” Part poncho, part shawl, the ruana is basically a wearable blanket that hails from the Andes, where staying warm is an art form. Whether belted in front over joggers or wrapped with a flourish over a cocktail dress, it is above all else flattering. Prices vary depending on fabrication. Made of viscose, Melifluos’ aptly named Shawl Wrap Poncho Ruana Cape comes in reversible solids or trendy leopard prints ($30-$40 at amazon.com). A luxe version from CashmereBySLD sports five-star reviews ($170 at etsy.com).

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