The Winter Workwear Rules Stylish Women Follow—and the Ones They Ignore

There's a point every year when getting dressed for work is actually fun. The humidity is gone, you can wear trousers without sweating through them, and the coats you've sacrificed precious closet space to store all summer finally get some use. After months of trying to dress for both 90-degree weather and an office that feels like a refrigerator, sweater weather is a welcome change.

But by November, the cold brings a whole new set of problems. You leave the house bundled up, only to spend the first 10 minutes at your desk peeling everything off. Bare ankles were fine last week, but now you're wondering if you missed some unspoken deadline for wearing socks. And while you'd happily spend the next four months in a giant knit, you do still have to go to work (and look presentable).

Office dress codes don't offer much guidance, either. Jeans are allowed in plenty of workplaces, but that doesn't mean every pair is appropriate for a meeting. A great coat can save an otherwise forgettable outfit, until you take it off.

For the cold-weather installment of our workwear guide, we asked women in fashion, beauty, design, media, and business about the rules they follow when getting dressed for work. Some are in an office five days a week. Others spend their days going between meetings, shoots, appointments, and airports. They don't agree on everything. One woman dresses for the morning temperature, another would rather freeze on her commute than carry an extra layer. But they've all figured out a few ways to get through the colder months without letting the weather dictate everything they wear.

In the ’90s, Casual Friday was a genuine workplace novelty. By 1994, nearly half of America’s 1,000 largest companies had adopted some version of it. Today, denim, for the most part, can make it through the front door without anyone blinking. The question now is which jeans—and what you wear with them.

Start with fit. Lawyer and tech founder Kameron Monet looks for a clean hem, precise tailoring, and, when the occasion calls for it, a dark wash. A pointed-toe heel helps, she says, but “it can’t save jeans that don’t fit.”

The rest of the outfit can do some of the work, too. Mara Roszak, hairstylist and founder of RŌZ, offsets oversized vintage Levi’s with a silk blouse, kitten heel, or blazer. Maisonette co-founder Sylvana Ward Durrett relies on a sleek leather belt to make a pair feel more intentional rather than thrown on.

Some old restrictions can go. Jamie Hunter, fashion and creative director at Poshmark, remembers working at Bergdorf Goodman 15 years ago, when only dark washes were allowed and testing the limits got her in trouble with HR. She now wears light washes and white jeans, but still draws the line at holes. Sarah Holme, head of design and product development at Old Navy had a tried-and-true formula. She pairs dark-rinse wide-leg or curved-leg jeans with an oversized button-down, a tailored jacket, and an animal-print kitten heel.

The first morning that dips below 60 degrees is practically an invitation to wear the sweater you've been staring at since August. Never mind that it's supposed to be 75 by lunch. Merie Subryan, founder of Studio Subryan, recently made the mistake of wearing a mohair sweater on a chilly morning, only to end up at H&M buying an emergency T-shirt when the sun came out. Her advice? Don't go “too heavy, too fast.”

That doesn't mean just dressing for the afternoon. Subryan is firmly on the morning forecast side. She'll wear an oversized crewneck over a button-down or T-shirt, then move it to her shoulders or waist as the temperature climbs. She'd rather carry an extra layer home in her tote than freeze on the way to work.

Storm Ascher, founder of the nomadic art gallery Superposition, would rather be cold. “I dress for what I'm doing that day, not the temperature on the commute,” she says. Her days take her between gallery visits, art fairs, and airports, so carrying a coat around isn't especially convenient. Instead, she wears thin mesh tops under her clothes, adds stockings for warmth, and keeps a silk scarf handy for chilly mornings.

When I worked in retail, there were actual rules about when you could wear tights and when you could go without. Office dress codes have relaxed considerably since then, but there's still a point every fall when bare ankles start to look awkward. The trouble is, nobody tells you when you've reached it.

For designer Veronica de Piante, the deciding factor is the rest of the outfit. She'll show a little skin between cropped trousers and her flat Margaux boots well into October, but once the heavy winter coat comes out, she covers up. “When the ankle looks cold, it stops working,” she says. “I think your eye tells you before your skin does.”

De Piante also follows a rule she learned from her father: Match your socks to your trousers, not your shoes. She likes fine ribbed or cashmere styles in brown, gray, and navy. With skirts, she wears opaque tights in the same color as her boots to avoid a visual break at the ankle.

Sali Christeson, founder of Argent, pays attention to the relationship between boots and hemlines. She wears chunky styles with wide-leg trousers that nearly reach the floor, and pairs slimmer, pointed-toe boots with narrow pants and longer skirts. For work, she recommends a leather pair with a flat or low heel that can handle the commute, meetings, and dinner afterward.

We've all been guilty of putting on a great coat and hoping nobody asks us to take it off. Katie Sturino, founder of Megababe, admits it's part of her “strategic winter dressing program.” She loves her coat collection so much that she's considered keeping a spare pair of Coldies in her bag, just in case she needs an excuse to leave one on indoors.

But there's a limit to how much work a coat can do. As Sturino points out, eventually you'll have to take it off, whether you're sitting down at your desk or heading into a lunch meeting. Her solution? Add a third piece to the outfit underneath. A scarf, a sweater draped over the shoulders, or a substantial belt can make the difference between simply wearing pants and a sweater and having an actual outfit. And don't assume that colder weather requires a more serious wardrobe. Sturino is firmly against retiring color and prints just because the temperature drops.

Nicole Wegman, founder and CEO of Ring Concierge, has a different insurance policy: jewelry. She's learned this lesson from wearing her Max Mara Teddy Coat season after season. Once it comes off, a pair of diamond studs or a tennis necklace can do a surprising amount of work. For days when a blazer feels too corporate, she prefers a crisp white button-down with chunky gold necklaces. And if you're wearing neutrals, as Wegman often does, she recommends mixing textures and paying attention to tailoring. Otherwise, even the best coat in the world isn't going to save what's underneath.

There's a reason so many people who work behind the scenes wear black. For Sue Chan, founder and chief creative officer of Care of Chan, a creative agency behind events for brands including J.Crew and A24, it's practically a job requirement. Her days can involve everything from site visits to meetings to late-night events. “It's also basically the unofficial uniform of event producers,” she says. More importantly, everything in her closet goes together, which means one less decision to make before leaving the house.

The challenge, of course, is keeping an all-black wardrobe from looking like the same outfit every day. Chan's solution is to mix materials rather than colors: leather with cashmere, pleats with wool, or something sheer against a heavier fabric. When everything is one color, the differences in texture become more noticeable.

Her other requirement is practicality. Clothes need to survive flights, long days, and the occasional back-to-back event without requiring a trip to the dry cleaner. She's particularly loyal to Issey Miyake's Pleats Please, which packs down to almost nothing, resists wrinkles, and can be washed at home. When packing shoes, she follows a simple formula: one flat, one mid-heel, and one high heel. And because everything is black, she doesn't have to spend much time figuring out which pair goes with which outfit.