Dressing Michelle Obama, Then and Now

On Tuesday evening, when Michelle Obama appeared on stage at the United Center in Chicago for the beginning of her 10-city, 11-stadium rock concert — oops, sorry, book tour, in an off-the-shoulder white sequined shirt that echoed the shirt in her cover photograph, plus high-waist white pants (both by Sally LaPointe), the reaction was unfettered and instantaneous.

The crowd loved her! They loved her honesty about her marriage and President Trump! They loved her memoir, “Becoming.” And they really loved her new look.

Cringe if you want, but as surely as you can bet that she’ll go high, you can bet that for the next four weeks your social media feed will be dominated by analysis of her every appearance and a detailed itemization of what she wears. It has already begun, with a cover from Elle magazine featuring Mrs. Obama, laughing, in a crisp white shirt, pleated skirt and black leather corset by Dior.

Inside, the photos show a paper-bag-waist silver satin culottes and jacket (Ms. LaPointe again) and a sheer Ann Demeulemeester top over a bodysuit, both prompting kudos on social media parsing her edge, and experimentation.

Such scrutiny was practically a national obsession during Mrs. Obama’s White House years, as she notes in her memoir, writing: “It seemed that my clothes mattered more to people than anything I had to say,” and “Optics governed more or less everything in the political world, and I factored this into every outfit.”

That scrutiny has continued through her rare public forays since: at the unveiling of her official portrait at the National Gallery, in which she wore a much discussed geometric -print Milly gown; at the 2017 ESPY Awards, when she presented the Arthur Ashe Courage Award in an asymmetric black Cushnie dress. And it’s only going to get more pronounced as people parse her future intentions through her clothes.

There’s an appetite for the nuanced way Mrs. Obama used fashion both as a tool and a celebration (as opposed to, say, a defensive measure). All of which makes her every fashion choice even more freighted, and none of which has escaped the woman who, starting during Mrs. Obama’s second year in the White House, has helped her put it all together: Meredith Koop. (Ms. Koop styled the Elle shoot, so the clothes reflect Mrs. Obama’s idea of herself, not the magazine’s.)

“I met Meredith when she was a young sales associate about a decade ago, and ever since, I’ve been blessed to have her by my side,” Mrs. Obama wrote in an email. “Together, we’ve prepared for every sort of event — from afternoons in T-shirts and gloves in a garden with middle schoolers to evenings in formal ball gowns with heads of state. Over the years, I’ve come to depend on Meredith for far more than wardrobe. She’s ridden with us through eight hectic years. She’s been a friend and mentor to our daughters. And she’s given us all a sense of comfort and home, no matter where in the world we might be.”

For years, Ms. Koop, a 37-year-old from Missouri with the height, broad cheekbones and bright blue eyes of the Midwest, functioned largely behind the scenes, but since the end of the Obama administration she has slowly emerged from the shadows. But the book tour is about to carry her — or at least her work — to the edges of the spotlight.

It’s a role she is not entirely comfortable with, in part because her biggest calling card is the one she is most apprehensive about appearing to exploit. (She has given only one formal interview, in 2016, when she was leaving the White House.) The mission now: to define what the next stage looks like. Not just for the former first lady, but for herself.

Can the approach that continues to help make Mrs. Obama such a resonant figure — one that involves choosing clothes not just for how they look (cute!), but also for the values they represent — be applied to the lives of regular women?

Is there a place outside politics for a stylist with an agenda?

The Anti-Stylist

These days Ms. Koop spends most of her time in a bright second-floor walk-up apartment in Brooklyn Heights, furnished with a cream sofa and some green plants. She moved there in 2017 with her boyfriend, Tomas Pagan Motta, a musician she met during her time in Washington. (He was working in the archival department.)

She has a small office off the bedroom but works mostly on her computer at the dining room table while sitting on a balance ball chair. In her bedroom are rolling clothes racks that slide under the bed when not in use.

Ms. Koop spends more time surfing e-tail sites and runway slide shows than sitting in the front row at fashion week or going to store openings. “I’ve always been an outsider,” she said one afternoon this summer when she was starting to plan for the book tour. “I think it makes me more approachable for people who are intimidated by the idea of fashion coming in their door.”

Ms. Koop did not set out to be a stylist. Growing up in St. Louis, she wanted to be a dancer. She went to Vanderbilt University and ended up living with her older sister in Chicago. One day she saw an ad in a paper for a sales associate at a clothing boutique and decided to apply.

The boutique was Ikram, a Chicago store run by the charismatic Ikram Goldman, a retailer with an uncanny ability to match clothing and clients and deep personal relationships with the women whom she dresses. (Her fans include Mellody Hobson, the high-profile Chicago asset manager and philanthropist, and Desirée Rogers, the former White House social secretary and Johnson Publishing executive.) Ms. Koop spent some five years there, “exposed to so many different types of women, women that are out there in the world doing something.”

“It was extraordinary training,” she said, “although I did not realize it at the time.” One of those women was Michelle Obama.

When Barack Obama embarked on his first presidential campaign, Mrs. Obama had enlisted Ikram as her wardrobe adviser, and Ms. Goldman had become a key figure in defining what became the “Obama style” — that is, one focused on using the attention that came with the job to support independent and emerging American designers, bridge all price points and break the first lady pastel skirts-and-suits mold. (The J. Crew outfit Mrs. Obama wore on “The Tonight Show” with Jay Leno was Ms. Goldman’s idea.)

But Ms. Goldman was running a business and couldn’t move to D.C., so she was looking for a person to facilitate communications. Ms. Koop was young and didn’t have anything keeping her in Chicago. And she could recognize an opportunity.

She started as a general aide, and in 2010, after Ms. Goldman stepped away from her unofficial White House role to focus on her store, Ms. Koop became the first lady’s de facto stylist in the Ikram mode: exploring “the patchwork of America.” Which is when she learned what it really involved. Which is pretty much what all dressing involves, only with much higher stakes.

Dressing the First Lady

“You have to anticipate every avenue of attack and every possible outcome,” Ms. Koop said, remembering. Everyone has an opinion: This dress is too informal; that is too frilly; this is expensive; that is too conceptual.

“You have to celebrate fashion but also be aware of the message people are going to take away,” she said. “Fashion can bolster communications in the best-case scenario, or be a silent partner, or actually distract.” Every outfit involved gaming out every possible reaction, good or bad, that she could imagine.

She would go along to meetings with policy experts and the foreign relations team. She would research the countries where the first lady was traveling, target a look and finally show the first lady.

“I would try to make a case for things: This is why it makes sense, why this designer, this cut,” Ms. Koop said. “Then we’d ask, ‘Do you like it?’ And then we’d think about logistics: What surface are you walking on? How many events? Will you be sitting? Will you be standing?”

To get the clothes, she emailed designers directly. “Her (and Mrs. Obama’s) vision for how Mrs. O wants to look for each event is always crystal clear,” Tracy Reese said in an email (Ms. Reese made the pink and silver sleeveless dress Mrs. Obama wore to the Democratic convention in 2012, among other looks). “In spite of all the scheduling and logistics involved, she somehow also manages to keep the process light and collaborative.”

Narciso Rodriguez, whose marigold dress Mrs. Obama wore to her husband’s final State of the Union in 2016, said much the same: “She is matter-of-fact about what she needs and lets you do your thing.”

Mrs. Obama had the final O.K. but didn’t question her beforehand. “She just frickin’ believed in me,” Ms. Koop said. She didn’t want to say more, she said, because she “would cry.”

But then it was over (or mostly over), and she was left wondering what to do next.

“I talked to a lot of celebrity stylists but didn’t hear many positive things about their business,” she said, sipping water from a Mason jar. “I didn’t want to be in the rat race of seasons, or promote the idea of disposable clothing, or something worn on a red carpet only once, or be in a room with a publicist telling me what to do. I didn’t want to just show up on a set and style for an advertiser.”

But she didn’t want to leave fashion, either. She wanted to do what she was doing but for a wider variety of people. She wanted to focus on emerging designers or names outside the fashion establishment, and introduce them to shoppers who tend to gravitate to what they already know. Instead of always considering the diplomatic message, she thought it would be interesting to think about the humanist message. It just wasn’t clear exactly how to style that job.

From the White House to the Wing

One afternoon in October in the Flatiron branch of the Wing, the co-working space for women, some members were hovering in the entry to a small back room. Along one wall were racks filled with basic pieces from Cuyana, a line focused on local production and started in 2011 by two business school graduates with the mission statement “Fewer, better things.”

Ms. Koop had been enlisted by the Cuyana founders, Shilpa Shah and Karla Gallardo, to do some “guest styling appearances” and help women understand how to define their style.

Ms. Koop, wearing high-waist jeans, kitten heels and an “I’m a Voter” tee, was trying to speed-psychoanalyze each potential customer in 20-minute slots. “Are you a dress person?” she said to one young woman. “Sometimes a blazer or suit can feel like a costume, like you’re trying too hard to be a boss,” she said to another.

A young woman in a striped dress and sneakers appeared. “Are you really Michelle Obama’s stylist?” she asked. “That’s so cool.” Then she said: “I recently realized crop tops are not right anymore. But what’s next?”

Later Ms. Koop said: “It’s so complicated now to be a woman. You want to be yourself, and you want to look good, but you don’t want to be objectified, and you don’t want to wear a bag.”

Her time now is generally divided between projects like the one with Cuyana and another she is doing with the American Civil Liberties Union that will bring it together with the fashion community to brainstorm ways to use clothes beyond simply making a message T-shirt.

She also designed a raincoat for Everybody World, a label started by the onetime American Apparel designer Iris Alonzo as a sort of hub for like-minded creatives with an eco bent. It has an adjustable waistband to fit as inclusively as possible and will go on sale in February.

She is working on a TV series as well, with the production company Honto88 (it made the #MySentence P.S.A.s on prison reform) that will look at the way fashion reflects the culture of its day. And she still does personal styling.

She has about 10 clients (which include two men, as well as the first client), ranging in age from their 20s to their 60s, and in size from 4 to 20. She spends a lot of time talking to them about their lives and going through their wardrobes. She brings along a tailor, Christy Rilling, because she often reworks pieces they own to update them. She won’t buy fast fashion. And she is still not convinced she has found the right balance.

“I don’t want to be styling people in five years,” Ms. Koop said. “It’s not really a business you can scale, because in the end, I have to be there.” For now, she is focused on the book tour.

“I really want what she wears to reflect her in a genuine way and resonate with what is in the book,” she said of Mrs. Obama. “For a certain percentage of the country, these are depressing times, and there’s a fine line between acknowledging that and celebrating her for who she is as a woman. Plus, a lot of her message is about connecting to younger individuals. So what does all of that look like?”

She is thinking a mix of designers, including names Mrs. Obama has not worn before (just to make that umbrella even more inclusive), but she’s not thinking dresses because they have too many associations with Mrs. Obama’s time as first lady. And because they make her think of the word “relic” more than the words “powerful” and “chic,” which are those she thinks Mrs. Obama should be going with.

She’s thinking more pants.