Martha Stewart on Becoming Sports Illustrated’s Oldest Swimsuit Cover Model – Do Dress Sneakers Belong in the Oval Office? – She Used to Assist Hollywood’s A-List: Now She’s the Boss

At 81, the domestic goddess fronts the magazine in glamorous swimwear that leaves little to the imagination. Her motivation? ‘Showing people that a woman my age can still look good and feel good’

By guest author Rory Satran from the Wall Street Journal Magazine.

Rory Satran


Updated May 16, 2023

Martha Stewart’s sex-symbol era began anew in her late 70s, when she posted a photo of herself on Instagram emerging from her East Hampton pool and called it a “thirst trap.” Since then, the CEO and mogul has reinvented herself from bumpkin to bombshell, more likely to attend gala events in luxe Hermès outfits and full makeup than to plant bulbs in khakis as she did in the 1980s. Today, she’s come full circle in her late-in-life glow-up by becoming the oldest woman to appear on the cover of the Sports Illustrated Swimsuit issue.

“Is it a sex symbol, or is it a symbol of healthy living?” asked Ms. Stewart, 81. “We can hardly say sex symbol nowadays, right? Overt sex is kind of frowned upon.”

Nonetheless, the businesswoman appears in glamorous, revealing swimwear that leaves little to the imagination. The photos were shot in the Dominican Republic by Ruvén Afanador, whom she trusted immediately because he first took Ms. Stewart’s portrait in 1993. She appears in several swim looks, including lounging on a couch in a white one-piece maillot and being doused by water in a silver metallic zip-up. The white deep-cleavage “Aruba” one-piece she wears on the cover, by Monday Swimwear, is already sold out in some sizes. Call it the Martha effect.

I’ve been hearing from people I haven’t heard from in years,’ Martha Stewart said of the response to her photo shoot. Photo: Ruvén

The reaction to Martha dwarfed the announcement of this year’s other covers, featuring Megan Fox, Brooks Nader and trans pop star Kim Petras. Most responses were positive. Writer and podcast host Evan Ross Katz wrote on Instagram that the cover was “the serve of the century” on a post that has 37974 likes and counting, and more queen emojis than I could count.

When I mentioned the profusion of queen emojis to Ms. Stewart, she laughed and joked, “The queen is dead so long live the new queen!”“I’ve been hearing from people I haven’t heard from in years,” Ms. Stewart told me, saying she’d been too busy in meetings to take all the calls. “Can you imagine being congratulated for a cover? I was never congratulated for all my covers on Martha Stewart Living.”

Ms. Stewart said she looked at the cover shoot as a challenge, and relished the opportunity to be the oldest woman to front the publication. In a video for Sports Illustrated, Ms. Stewart said, “Usually I’m motivated by pay, but this time I was motivated by showing people that a woman my age can still look good and feel good.” For the work, she was given the standard editorial rate that Sports Illustrated pays all models—little enough for Ms. Stewart to say she was “not paid.”

The businesswoman, who modeled decades ago to put herself through Barnard, took the physicality of the shoot seriously. She forwent bread and pasta for a couple months. She does reformer Pilates every other day at 6:30 a.m. with a private instructor in her hometown of Bedford, N.Y. Ms. Stewart said she was told that she did more reps than anyone else, going for 100 when others would be satisfied with 10. She drank her standard green juice every morning, which she told me had not changed since we last spoke in 2020, except for the subtraction of pineapple which has been deemed too sugary.

Swimsuit 2023: Dominican Republic Martha Stewart Casa de Campo 2/1/2023 X164302 TK1 Credit: Ruven Afanador

“Everyone is over the moon about Martha,” said Sports Illustrated Swimsuit editor in chief MJ Day, who has helmed the magazine for 12 years. For Ms. Day, the Martha cover is a continuation of a project the magazine has been undertaking for several years now to highlight a wider range of ages. In 2022, one cover featured then-74-year-old Maye Musk, and in previous years the magazine has featured then-60-something Christie Brinkley and then-50-something Paulina Porizkova.

Ms. Day rejects the idea that the magazine is solely for men, arguing that women have always looked to it for swimwear trends. And recently, that female readership has grown. She said, “We’ve always had this unsung demographic of women that we weren’t really speaking directly to. And as we’ve done that over the past decade-plus, that reach and that conversation and that connectivity, those touchpoints have grown exponentially.”

Ms. Day, who is 48 and told me she wears a size 12, said that inclusivity was important to the brand. Part of her job, she said, is “continuing to have those important conversations for women that we can see ourselves outside of the very stringent parameters that we’re used to seeing ourselves represented in.”

Kim France, the former editor in chief of Lucky magazine and the podcaster and blogger behind “Girls of a Certain Age,” was not overwhelmed by the Sports Illustrated Swimsuit statement.  “It looks like a big risk, but I think it was a small risk,” she said, calling the annual issue a relic. Multiple covers may help the magazine project an inclusive image, she said, but it waters down the message of featuring an octogenarian: “I feel like if they put her on the only cover they had on newsstands, then I’d be impressed.”

As for Ms. Stewart, she looks forward to reading the comments on all the posts, and then getting on with her life. In the next 10 years, she said, “I care more about watching the evolution of my grandchildren than I care about watching my evolution.”


Do Dress Sneakers Belong in the Oval Office?


People felt strongly after spotting the hybrid shoe at a meeting with the president.

By guest author Guy Trebay from the New York Times Magazine.

From left, Senator Mitch McConnell, Speaker Kevin McCarthy, Vice President Kamala Harris, President Joe Biden, Senator Chuck Schumer and Representative Hakeem Jeffries in the Oval Office.Credit…via @WhiteHouse

May 19, 2023

Think of it as a rare instance of cross-aisle consensus or else a sartorial trend gone badly wrong. But it did not go unnoticed when, in a photograph from the Oval Office posted to President Joe Biden’s account this week, Speaker of the House Kevin McCarthy, Senator Mitch McConnell and Representative Hakeem Jeffries were all captured wearing some variant of the dreaded footwear hybrid: the sneaker shoe.

Weighing in on Twitter, cult men’s wear commentator Derek Guy (@dieworkwear) called out the footgear as a clear lapse in dignity, if not actual protocol. Why pay a visit to a sitting president dressed in shoes designed for power-walking at the mall?

“Awful,” Yang-Yi Goh, style director of GQ, pronounced the shoe that has become a style default among Capitol Hill staffers.

Yeezy on the sole and granddad on the uppers, the Cole Haan shoes (Mr. McConnell, for the record, was wearing the label’s ZeroGrand; Mr. McCarthy, the Osborn; and Mr. Jeffries, the Grand Crosscourt II) have neither the street cred nor the advantages of actual sneakers, like the Nike Dunk Low “Montreal Bagel” model that stoked debate when the “Ted Lasso’’ star Jason Sudeikis and his castmates wore them to the Oval Office in March — there to discuss mental health care in the United States.

“Call me old fashioned but no man should set foot in the Oval Office without dress shoes and especially not sneakers,” the political commentator Saagar Enjeti said at the time, unleashing further invective in a Twitter post: “4 guys. No ties, 3 pairs of sneakers in the Oval Office. This country is going to hell.”

But is wearing a squishy shoe that masquerades as a hard-soled one really all that terrible? “The hybrid is the worst possible choice,” said Mr. Goh of GQ, the footwear version of political bait-and-switch, akin to a novelty tie or a garish pocket square. It does not help matters much when, as in the cases of Mr. McCarthy and Mr. Jeffries, the soles of your shoes are glaring operating-room white and the accompanying socks are striped.

“You’re trying to pass this tech-y monstrosity off as a proper dress shoe,” Mr. Goh said, adding that a suit and necktie worn with a traditional hard-soled shoe symbolise respect for occasion, in this case a meeting with the most powerful man on earth.

For Jim Moore, the creative director of GQ and the stylist largely responsible for Roger Federer’s impeccable swagger, a hard-soled shoe serves as a “sign of courtesy and good manners” in most formal settings. A solid pair of lace-ups — many of which, it’s worth pointing out, are manufactured nowadays with comfortable rubber soles — provides the foundation for a suited wearer. “When you see a guy strutting through the city in a suit and your eye reaches the sneaker, the whole look collapses,” Mr. Moore said.

Like the stretchy mid-blue suits favored by many men, including Mr. McCarthy, the optics of the “dress sneaker” would seem to have the opposite of the desired effect. Rather than imparting to their wearer a vigorous, youthful look — as President John F. Kennedy’s forelock once did — they appear strenuous, over-considered, the more passé because young consumers have turned increasingly toward the foolproof formulas of classical tailoring.

“It’s literally putting your best foot forward,” Mr. Goh said of a pair of well-buffed Oxfords — or even the loafers that were once thought too schlumpy to be worn in business settings. The implicit formality of a hard-soled shoe evinces respect for the formality of an occasion destined to occur a limited number of times in any given life.

“Do one or the other,” Mr. Goh added. “Just commit.”


She Used to Assist Hollywood’s A-List. Now She’s the Boss


After working for Jennifer Lawrence and Madonna, Meghan Grimm is running her own business: a matchmaking service for celebrities and personal assistants

By guest author Lane Florsheim from the Wall Street Journal.

May 17, 2023

On a Tuesday in late April, Meghan Grimm and two of her college interns gathered around her dining-room table for an all-hands meeting. Improvising an office setup in her Greenwich Village one-bedroom, Grimm displayed a laptop on her kitchen island that featured a third intern on video and an elaborate, color-coded spreadsheet filled with the names of celebrities, executives and socialites.

“This is my second official day without Jen, so everything is a little crazy,” she said.

After almost five years as a personal assistant to Jennifer Lawrence, Grimm, 30, parted ways with the Oscar-winning actress to focus on her own company, Clyde Staffing Ventures, where she sets up entertainment-industry players with Meghans of their own. Her client list includes the actors Dakota Johnson, Anne Hathaway and Uma Thurman, and the model Kaia Gerber.

On the spreadsheet were 37 open positions she was working to fill for, among others, an A-list singer; a Gen-Z television heartthrob; both members of a divorced Hollywood couple; and a billionaire businessman in search of a “travel assistant.” Grimm calmly read through the list, noting whom she’d sent candidates to; who needed to see more résumés; and desirable qualities and qualifications for specific clients. She described one, a socialite and businesswoman, as “super polished and proper”—Grimm wanted to send her candidates who were, too.

“I think being an assistant is very much like dating—you have to be 100% compatible with your boss because it is such an intimate job,” she said.

Many stars have multiple assistants and a chief of staff whose job is to know and manage everything about their boss’s life. When a pairing is particularly compatible, the employer could one day become a best friend or business partner to an assistant. On the other extreme, assistants may find themselves at the whims of a tyrannical or abusive boss. Some examples veer into parody: Earlier this year, an executive-assistant job listing for a New York power couple went viral for its extensive list of responsibilities, including managing dog potty breaks and packing the couple’s bags ahead of travel.

Grimm said that for most assistants, a good work-life balance exists, “as long as you’re aligned on boundaries and expectations.”

Meghan Grimm and her French bulldog, Tate.Meghan Grimm and her French bulldog, Tate.

There are established entertainment-industry staffing agencies, including the Grapevine Agency, Career Group Companies and Hire Society. Grimm said that her experience as an assistant puts her in a position to ensure that talent will have the support they need and place assistants in roles that will be fulfilling.

“Years ago, many applicants were willing to work for much less money,” said Rachel Zaslansky Sheer of the Grapevine Agency, adding they were up for longer hours, too. More recently, she said, balance is a top requirement.

“When people heard that I’m an assistant, what would really offend me is when someone would say, ‘Oh, what do you do all day, dry cleaning and errands?’” Grimm said, whereas the job often entailed much more.

“You are their gatekeeper, you oversee projects, you deal with vendors, you are on set. You’re wearing one million hats, and you pretty much learn how to do everything, with contacts in every city,” she said.

“If your boss is getting married, helping them plan their wedding,” she went on. “If your boss is moving into a new home, overseeing that entire move with art and furniture and personal effects and household construction from the ground up. If your boss has a company, you are sitting in those meetings. You’re their right hand.”

Lawrence, Grimm’s former boss, echoed that sentiment. “Meghan played an integral role, really as the COO of my life,” she said. “She kept me organised, advocated for me, protected me and was always five steps ahead.”

Seeing herself as a mentor figure to the assistants she places, Grimm said she trains each one before they start their job and makes herself available to both them and their bosses whenever they need. “I’ll have a client who will say, ‘Could you please do a Zoom with my assistant tonight? She’s never been on a movie set, do you mind walking her through protocols and just giving her some advice?’” she said. If a placement doesn’t work out within 90 days, she refunds the client and works on finding another candidate for them. So far, this has happened once.

  All the good jobs are word-of-mouth,’ the former assistant says of her industry.


In addition to her staffing services, Grimm created a Slack workplace that Clyde assistants and other assistants in her network can join as long as they sign an NDA. She described it as a “little black book,” where members—who identify themselves with both their own name and their boss’s—can trade tips about private chefs, upscale jewelry-repair services and nannies in specific cities where their bosses are shooting or touring. “We have a person for everything,” she said.

Grimm said she wishes people understood that bad bosses are the exception, not the rule. “I think people have a really bad taste in their mouth about assistant jobs because of what you’ll read from one experience,” she said. “My number one goal is to have better fits all around to avoid that problem.” She said she has only turned down one client. If a business relationship goes south, she said, it’s usually because the two people weren’t a fit.

Grimm grew up in Manhasset, N.Y., and studied English at Georgetown University. After graduation, she worked her way up the assistant ranks at Ralph Lauren, ultimately assisting the vice president of communications. While helping to style celebrities at the fashion company, she realized she could bring her assisting talents to Hollywood. Before working with Lawrence, Grimm assisted Madonna, the actor Tim Blake Nelson and the producer Casey Patterson. She donates a percentage of her proceeds from Clyde to Madonna’s charity, Raising Malawi.

“She’s resourceful to a fault,” said Florinka Pesenti, Grimm’s former boss at Ralph Lauren. “Like she found me every babysitter I’ve hired—this was after she worked for me.”

Before starting Clyde, Grimm was doing the sort of matchmaking her company offers, setting up students from Georgetown and Manhasset looking to get into entertainment with assisting gigs. “All the good jobs are word-of-mouth,” she said.

In early March 2020, she flew to Los Angeles with Lawrence, contracted Covid and spent the first months of the pandemic isolating in a hotel room with her French bulldog, Tate. Work was slow, so she started drafting plans for Clyde.

On a call in her apartment, Grimm spoke to the agent of a model and businesswoman who was looking for her first personal assistant. The agent asked for a typical assistant salary. “If it’s an entry-level assistant right out of school, you’re looking at USD 50 to USD 60000,” said Grimm, “but you’re not getting someone who has done this job before.” Someone with two years of experience could expect to make USD 70000 to USD 80000; a seasoned assistant could take home a low six-figure salary; and a veteran, USD120000 to USD 150000 and up. Grimm’s clients pay her a fee equivalent to 20 % of first-year pay.

One of the Clyde interns put all of the open positions onto Clyde Staffing’s Instagram Stories and tagged the popular celebrity gossip account @deuxmoi with invisible ink. DeuxMoi reposts job listings from Clyde to its 1.9 million followers. Grimm is also developing relationships with colleges with film programs to recruit potential candidates.

“If a candidate writes me and reiterates how happy they are, then there’s this increase of people doing these jobs,” said Grimm. “They tell their friends, their friends tell their friends, and now people want to become an assistant. That’s what I’m trying to create.”