Of all the places a person might feel at home in her clothes, the Academy Awards does not immediately come to mind. The Oscars are the pinnacle of celebrity theater, with attendees buffed to superhuman levels of glamour and sheathed in couture gowns.

But Maya Rudolph wasn’t dressed like most attendees at the awards show in 2018. In a sea of sequins and flowing trains, the actress and “Saturday Night Live” alumna stood out in a bright red Valentino turtleneck jumpsuit with wide legs and loose sleeves that tapered at the wrist, her hair parted down the middle and slicked into a low bun, with a pair of dangly Irene Neuwirth earrings framing her face. She looked bold and glamorous, but also comfortable.

It was, Ms. Rudolph said, the first time she felt like herself on the red carpet. Not coincidentally, it also was her first time working with the stylist Rebecca Grice, who has dressed her for public appearances ever since.

“The stuff we connect on is usually the stuff that we’re both kind of wincing at with one eye, going, ‘That’s sick,’” Ms. Rudolph said in a phone interview. Words like “twisted” and “witchy” also tend to come up in their sessions. They go for looks that have a wink to them — outfits that, Ms. Rudolph said, are “not typically what you expect to see, and yet so incredibly beautiful.”

For the better part of a decade, Ms. Grice, 39, has been cultivating a clientele that leans noticeably toward women who, like Ms. Rudolph, are professionally funny. Her roster includes several “S.N.L.” players past and present — Aidy Bryant, Kate McKinnon, Vanessa Bayer — as well as the Haim sisters Este, Danielle and Alana (best known for their music but also notably hilarious). Each has a distinct style, but Ms. Grice, across her body of work, seems inclined to make a statement in the most low-key way possible — a welcome retreat, perhaps, from the wigs, goofy costumes and stage makeup of a sketch comic’s work life.

“Rebecca has a relaxed quality to all her styling,” Ms. Bryant said. “There’s kind of a ‘What’s the big deal?’ feeling about all of her outfits, even when it’s what is on paper kind of a frilly dress.”

Since she started working with Ms. Grice, Ms. Bryant often wears what could be described as frilly dresses, particularly ones by Simone Rocha, an Irish designer whose voluminous, ruffled silhouettes evoke a subversive kind of femininity. A floaty pink dress with cartoon-princess sleeves and a dainty floral pattern is a head-turning look, but it’s also the kind of dress that accommodates reclining on Seth Meyers’s couch (or desk). Ms. Bryant values a sense of normalcy in dressing for appearances. “I like to feel like I’m one step away from my everyday self,” she said.

Ms. Grice doesn’t have a tidy philosophy about styling professionally funny women. But speaking over Zoom in January from her home in Los Angeles, she noted one tenet: “Comfort is key, and comfort is confidence.”

Like so many, Ms. Grice had become accustomed to conducting business by video. That week, she had done a FaceTime fitting with Ms. Bryant for “Late Night With Seth Meyers” (resulting in the aforementioned floaty pink dress); dropped off some options for Ms. Rudolph, who was doing a virtual press day for the animated movie “Luca,” then discussed them remotely; and held an in-person fitting with Alana Haim to figure out her look for Pharrell Williams’s podcast, which was filmed in addition to being recorded on audio. (Ms. Grice said that she and Ms. Haim live near each other and are in the same “bubble.”)

Ms. Grice much prefers to be in the same room as her clients: Good stylists know how to read a client’s energy and vibe, intuiting when to push them toward a more daring look and when to ease off, and it’s easier to do in person.

But being able to adapt to new circumstances is also a prerequisite of the profession, she said. “You just have to adjust, or else you will drive yourself nuts,” Ms. Grice said. “It’s never enough time, it’s never enough money, there’s never enough help.” When the pandemic slowed down her workload and scrambled her schedule, she rolled with it.

Among her clients, she is known for having a grounded, unflappable demeanor and for being, as Ms. Bayer put it, “extremely cool.” (Not in a way that makes you feel intimidated, she added, but in a way that makes you want to emulate her.) But even cool people have their cool people: During one Zoom call, Ms. Grice sent me some mood boards she’d created for a client — she declined to give a name — that featured archival photos of Lauren Hutton in breezy, low-cut blouses and Kate Moss in undone suiting.

“Kate Moss is the end-all, be-all reference. She’s just the coolest,” said Ms. Grice. “And then Lauren Hutton just smoking a cig in a printed shirt and a leather jacket is pretty cool.”

The capacity to remain calm through fashion hiccups and global lockdowns may be innate for Ms. Grice, but it has also been honed over many years in the fashion industry. After graduating from Elon University in North Carolina, Ms. Grice moved to New York and landed at InStyle magazine, where she struggled to churn out 25-word blurbs on matters like day-to-night outfit transitions but learned what she considers foundational professional skills: hitting deadlines, communicating with P.R. people at labels and managing editors’ schedules.

She eventually left the magazine world and began to work for the stylist Lori Goldstein. “I feel like I’m classically trained by one of the greats,” Ms. Grice said. Under Ms. Goldstein, she learned how to grind through grueling photo shoots and worked with Steven Meisel, Mario Sorrenti, and Inez and Vinoodh.

Ms. Grice’s introduction to celebrity styling came through Mel Ottenberg, with whom Ms. Grice connected after leaving Ms. Goldstein’s team and who had recently started working with Rihanna. (He is now the editor in chief of Interview magazine.)

“Working for Mel exposed me to music videos, to red carpets, to ad campaigns,” Ms. Grice said. It also led to a solo gig styling Haim, then an emerging band.

Ms. Grice’s first shoot with Haim in 2013 was meant to produce the cover art of their debut album, “Days Are Gone.” Though they didn’t wind up using any of the shots, the relationship stuck. “I just really, really genuinely vibe with them on a deep level,” Ms. Grice said.

The Haim sisters are central figures in Ms. Grice’s world. They connected her with Ms. Bayer, whom they befriended when they were the musical guests on “S.N.L.,” and Ms. Bayer in turn suggested Ms. Grice to Ms. Bryant.

Ms. Rudolph met Ms. Grice in 2017, while her partner, Paul Thomas Anderson, was directing a short film for Haim; he wrote the lead role in his most recent film, “Licorice Pizza,” for Alana. Maya Erskine, of the painfully realistic middle-school comedy “PEN15,” also connected with Ms. Grice through the Haim sisters. They went to the same high school in Los Angeles.

Haim’s looks tend to have a loose ease that comes off as both very Californian — they grew up in the San Fernando Valley — and very rock ’n’ roll. They also show a keen appreciation for fashion: For their performance at the Grammys in 2021, Ms. Grice pulled vintage Prada and Helmut Lang looks. Danielle Haim in particular is a walking encyclopedia of fashion references and leads many of the band’s creative decisions, Ms. Grice noted. “In another life she would — or still can be — an amazing art director or creative director,” she said.

In public appearances, the sisters express their individuality while dressing cohesively, often in the same brand or with rhyming textures and color palettes. “She has an incredible eye for knowing what fits in our world,” they wrote of Ms. Grice in a joint email. “We are a band with three people with three different styles and she somehow fits us three puzzle pieces together to make something great.”

When Alana Haim started her press tour for “Licorice Pizza,” her debut film, Ms. Grice avoided looks that seemed typical of a bright-eyed ingénue. “Wearing gowns and dresses is new for me, but we both wanted to make sure that I was still me, just with a dress train,” Ms. Haim wrote in an email.

They went for Louis Vuitton trousers under a transparent skirt; draped, long-sleeved Loewe; a cutout lime green and gray ensemble by Nina Ricci; and, for “The Tonight Show With Jimmy Fallon,” a baggy camel suit from the Row with a turtleneck underneath. That last look, which Ms. Grice said reminded her of Katharine Hepburn, seemed particularly emblematic of the stylist’s approach: comfortable, cool and designed primarily for the woman wearing it.

“I don’t know if everyone understood it,” Ms. Grice said. “But I loved it.”