Why Is Dressing for Fall So Damn Hard?

Bianca Arlia, a 22-year-old from Rhode Island, cites Rihanna and Bella Hadid as her two “biggest inspirations” when it comes to fall dressing. “No one is doing street style like them,” Arlia, who works in retail, said. “Whether they’re dressing casually or going out, they always look so effortlessly cool.”

Inside My Epic, Disappointment-Strewn Search for the Perfect Winter Coat

She’d love to channel their layering prowess, whether it’s Rihanna in a marabou-lined mini skirt and sweatshirt slung over a black bra, or Hadid looking very Matrix-y in black leather flares and a quilted black jacket. But most of the time, Arlia conjures another unexpected autumnal influencer: midlife crisis-era Adam Sandler.

“I always get so excited to dress during fall,” Arlia explained. “I love it all, from cozy knit to pleather to flannels to faux fur. The reality is that most days I end up looking like Adam Sandler. Sometimes it’s just way too cold to care what you look like and he really gets that. Even though he’s worth tens of millions of dollars he dresses just like the rest of us.”

Arlia recently tweeted a paparazzi photo of the comedian out with his children in a classically unbothered Sandler outfit: stained New Balances, roomy sweatpants—the roomier ones that are made for crying in, not the cool athleisure kindan old graphic T-shirt, and a puffer jacket that has lost most of its volume and seen better days. Crucially, he’s carrying a white mug around, which seems to really tie the whole “I’ve given up” look together.

“I be like ‘i can’t wait for fall fits’ then fall comes and I dress like this,” Arlia wrote in a caption.

For all the excitement around fall dressing—expectations of sweater weather, leather jacket season, and the chance to bury yourself in varying shades of camel—the reality can be much more tough. Erratic temperatures make it feel like the dead of winter during a morning commute but midsummer by lunchtime. Why are you sweating if you also feel a chill up your spine? Are you having a stroke?

Cultural depictions of fall apparel are a lie. If there were any truth to the tree-peeping scenes in When Harry Met Sally, Meg Ryan’s bob would have been beaded with sweat as she walked around Central Park and she’d spend most of her afternoon pulling her sleeves up and then rolling them back down every five minutes or so. Ali McGraw in Love Story would have ended up wrapping that famous brown peacoat across her waist once the day warmed up. Go figure—we’ve been deceived by Hollywood renditions of autumnal scenes.

“The weather can change in minutes and varies greatly throughout the day,” Aja Heinlein, a 32-year-old Chicagoan, said. “What keeps me cozy grabbing coffee on a brisk morning has me sweating by the commute home, so I find that a lot of my personal comfort is sacrificed for fashion in the fall.”

But Heinlein, who works in customer support, still swears she loves her fall wardrobe. “I love the colors—deep burgundies and olive greens act like neutrals and complement rich jewel tones so well. I like to play with layers in the fall to see how I can extend the seasonality of my spring and summer wardrobe. I will often pair a long-sleeved shirt, bodysuit, or seawater under a jumpsuit or dress. This gives me the ability to transition my wardrobe between seasons; in doing so I find myself thinking more creatively about my outfits and overall buy fewer trends to focus on more versatile pieces.”

Heinlein added that it’s “certainly easier” to dress for other seasons, but she likes the challenge of a manic October day. “I find that the outfits I come up with in fall are a better representation of my personal style.”

Plus-size influencers are Heinlein’s greatest source of inspiration; she said she “doesn’t see a lot of celebrities who have my style or body shape.” Some of her favorites are Natalie Drue, Rosey Blair, and Teen Vogue columnist Charlotte Zoller.

Erik Maza, the style features director for Town & Country, agreed that people often have enough in their closet to dress for fall without running out to buy new knits. “Dig out all those clothes that have been in storage and reassess—what did you actually wear last fall? Is it going to bring you joy again? Editing is sometimes the first step towards happiness; trust me I speak from experience. In this case, fashion nirvana.”

Maza said his go-to fall outfit is a Brunello Cucinelli bomber jacket paired with light-wash jeans and comfortable sneakers—lately he’s been into the New Balance x Casablanca collaboration.

Kerry Pieri, the digital fashion and features director at Harper’s Bazaar, suggested “thinking of building your layers in terms of weight. Start with a thin T-shirt or button-down and build from there with knits and outerwear.” She’ll usually go out in jeans, boots, a T-shirt, an oversized tweed blazer, and a sweater tied over her shoulders. “This means at any point in the day I can be wearing just a T-shirt, a T-shirt and blazer, a T-shirt and sweater, or a T-shirt with a sweater tied over my shoulders for just a little warmth.” (That is, if you’ll touch the preppy and sometimes divisive sweater-over-shoulders look.)

Vogue fashion news editor Sarah Spellings added that it’s important to “make sure you like your outfit with and without your outerwear of choice, and be aware if you run hot or cold. I’d rather be too cold than too hot.” And if all else fails: “A great statement jacket can carry the entire outfit for you.”

Or a colorful sweater. “[Those] are making everyone smile this fall,” Spellings said. “I just saw that Bill Clinton wore a ‘breakfast sweater’ by Aime Leon Doré, and Princess Diana’s ‘black sheep’ sweater has been enjoying a major comeback since last year.”

Spellings, like Pieri, calls Princess Diana a fall dressing OG. “Diana in a cowboy boots, a blazer, and a baseball hat forever,” Pieri said.

“I always go with [Gossip Girl’s] Blair Waldorf—her Thanksgiving outfits are unmatched,” Spellings said. “Olivia Pope [from Scandal] also has everyone beat on coats and gloves.”

And then there’s always Diana Keaton. “[Dressing like her] in any Nancy Meyers movie is great, because keeping your look monochromatic while you layer is very chic.”

Maza, the Town & Country editor, just has two words for you: Margot Tenenbaum. “The Royal Tenenbaums came out 20 years ago and it’s still influential,” he said. “I would also keep tabs on Wes Anderson’s latest The French Dispatch, with costumes by the legendary and four-time Academy Award winner Milena Canonero.”

None of them listed Adam Sandler (sorry Sandler!), but hey: like Impressionist artists, not every great fall dresser can be enjoyed in their time.

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