As the year has flown from March to the near-end of October, what constitutes an everyday outfit has shifted from pajamas, to house dresses, to at summer’s peak, the bikini. But fall’s chilly temps require a bit more strategy than the one-and-done method. Getting dressed means focusing on items that are not only ultra-comfy, but that also promise to withstand the test of time (all with a focus on sustainability and small brands, too). Beyond mixing and matching sweats, you’ll want a selection of comfortable fall outfits that still feel elevated.
After months spent in loungewear, it’s time to return to the timeless pieces that provide comfort while simultaneously achieving the chic looks you know, love, and frankly, miss. Somewhere, in the far away closets of fashion directors, stylists, and otherwise “in the know” individuals, are modern takes on casual dressing re-emerge this fall. Hint: youthful knitwear and oversized silhouettes are great places to start.
While fashion has proven its relation to (and therefore, its ability to be influenced by) everything from the latest millennial-aimed Netflix show to era-defining social justice issues, there’s at least one thing which remains constant: you can count on the industry’s trendsetters to serve as inspiration. Oftentimes, those at the center of the industry have their own unique ways of interpreting mega trends each season, and they may even have an eye on micro trends you may not have tapped into yet. Below, eight stylish women in fashion share the fall looks they’re wearing on repeat. If their shopping carts are any indication, you’ll want these pieces in your hands ASAP.
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Comfortable Fall Outfits: Go For Oversized
Fashion’s collective embrace of all things oversized stems from any number of directions: as a branch of the menswear-inspired trend that swept social media feeds this summer, from the need for comfort sans loungewear, and as a vehicle for adding texture and shape to the minimalism trend. For Elisa Johnson, founder and designer behind Selected by Elisa, the appeal lies in pairing various shapes against each other. “I love to mix and match silhouettes and juxtapose more formal pieces with relaxed styles,” Johnson tells TZR. “[This allows] me to play with my style, and put together items that may not conventionally work together.” Among the pieces this trend trail blazer is throwing on before heading out the door these days? Joggers and an oversized blazer.
Comfortable Fall Outfits: The Laid Back Suit
A more direct tribute to menswear dressing, and in true WFH fashion, the ultra-structured power suit has quickly progressed into the loosely-tailored iteration. “Suits are always on trend in my book,” Kat Collings, Editor-in-Chief at Who What Wear tells TZR. “This season, I’m especially drawn to what I’m calling ‘soft suiting.’ It’s a little slouchy, a bit oversized, and perfect for maintaining a semblance of ‘I got dressed’ professionalism while working from your dining room table.” For styling her go-to, she suggests a classic: the turtleneck. “Thin, mesh ones are my go-to since I live in L.A., and I’ve had my eye on this hypnotizing Kai print for a while now.”
Comfortable Fall Outfits: Head-To-Toe Chocolate
Of all the fall color trends this year, Teen Vogue’s Fashion and Beauty Features Director Tahirah Hairston’s pick is the richest of neutrals, chocolate brown. For Hairston, the newfound love can in part be credited to the wardrobe styling of the early 2000s hit show, Girlfriends, which hit Netflix in September. “A chocolate slip dress or a pair of chocolate, square-toe boots would be the purchase of the season for me,” she tells TZR. Hairston also recommends leather Birkenstock sandals as an easy way to dress down the head-to-toe neutrals trend. “I wear them every single day,” she says. “They are easy to throw on, and I can’t wait to try them with socks this fall. Also, I’m going to invest in a super cozy shearling pair.”
Comfortable Fall Outfits: Leather On Leather
By now, Instagram might have you questioning whether or not you need another pair of leather pants in yet another neutral shade. The answer is yes according to Roopal Patel, Fashion Director at Saks Fifth Avenue. “I love leather for fall because it acts as a neutral in my wardrobe,” Patel tells TZR. “Leather keeps you warm, but is always sleek and chic, like a second skin, in the colder months.” Her go-to for styling is to add chunky boots, citing the Bottega Veneta lug-soles as a seasonal favorite. The two style elements together just may make for the ultimate fall combo.
Comfortable Fall Outfits: Knit All Over
If you have reached the point of ditching traditional loungewear, but with WFH still in place, are simply looking at elevated alternatives. For Arielle Sibioni, Women’s RTW Fashion Director at Bloomingdale’s, the solution is simple. Knits. “[I’m] looking forward to wearing knits head-to-toe,” Sibioni tells TZR. Try the trend by way of a sweater dress or try a matching set in a relaxed fit.
Comfortable Fall Outfits: Utilitarian Chic
While the future of the fashion industry remains in flux, Vanessa Hong, influencer, consultant and podcast host, is looking towards the juxtaposition of comfort and structure. “I think we’re seeing a lot more utilitarian trends like chunky boots, harder edged coats and outerwear,” Hong tells TZR. “Comfort is still super key — I think this can make for some really cool, individual, and comfier, street style.”
Comfortable Fall Outfits: Comfy Prints
For now, digital entrepreneur Alyssa Coscarelli has abandoned jeans for anything flowy, printed, and fun instead. “Jeans just feel so restrictive these days,” Coscarelli tells TZR. “I’m loving printed or patterned lounge pants that are super comfy, but I can still feel decent leaving the house in them.” If you’re loving ‘70s fashion right now, the right printed pants caters to the trend effortlessly, as do sweater vests, another item Coscarelli finds herself reaching for more often this fall. “[Sweater vests] just perfectly tap into that vintage-inspired, tomboy feel I’m loving right now,” she says, adding that sweater vests, too, come in an abundance of cool prints. The takeaway? Prints, please.
Comfortable Fall Outfits: All Fashion Girls Wear Capes
If you’re looking for a way to stay warm and stand out, consider the season’s cape trend, which swept the runway (literally) at Rick Owens, Givenchy, Balmain, and more. “I love their dramatic feel, but I also find them to be extremely practical,” celebrity stylist Madison Guest tells TZR. “They look great with so many outfits, but don’t weigh you down like last year’s puffer coat.” To finish the look she suggests split hem legging-trousers — namely, a pair from Zara. “They’re just as comfortable as my usual leggings,” she says, “but much more stylish.”