Michelle Obama shares untold stories behind ‘The Look,’ including that iconic pants outfit in case something popped off

EXCLUSIVE: During a live taping of her “IMO” podcast in Washington, D.C., Mrs. Obama reflects on her most iconic looks as America’s historic Black First Lady.

Michelle Obama had a homecoming of sorts on Wednesday night while promoting her new book, “The Look,” in Washington, D.C., the city where she first moved in 2009, becoming forever etched in U.S. and Black history as America’s first Black First Lady.

“I’m home,” Mrs. Obama said to thunderous applause at a live taping of her “IMO” podcast attended by theGrio at the historic Sixth & I in D.C., just a mile away from the White House, where she lived and served for eight years as the matriarch of the Obama First Family.

Wearing a vintage black-and-white dress by Zac Posen and joined in conversation with film critic Wesley Morris, Michelle Obama shared behind-the-scenes stories of some of her most iconic looks — and the inclusive and intentional messages, as well as the people, behind them.

“The Look” takes readers through 300 pages of storytelling and photography that capture Obama’s style and beauty before, during, and after her historic tenure as First Lady.

As the first Black woman in the role, Michelle Obama told the D.C. audience she learned very early on into her husband Barack Obama’s presidency that what she wore held more weight than any fabric draped around her body or styling of her hair.

The weight of America’s first Black First Lady

Mrs. Obama recalled some of the criticism about her gown at President Obama’s first inagural ball–a now iconic one-shouldered white silk chiffon dress by then-newcomer Jason Wu that exposed her toned arms. Obama was notably introduced to Wu by the late André Leon Talley, the former Black editor-at-large at Vogue magazine.

“This wasn’t a DEI hire,” said Mrs. Obama, referring to, but not naming, the Trump administration and the Republican Party’s attempts to ban diversity, equity, and inclusion. “This was the prettiest dress. It was the best dress.”

“The fact that something, you know, anything, was made of me wearing, having my arms out, was just a small indication of the kind of crazy attention that— or standard of beauty or acceptability— that was at play. So we knew that everything was going to send a message,” she shared.

“The dress was beautiful, but we were beginning to realize that everything we did sent a message. Sometimes people would read the wrong thing into a fist bump,” added Obama, referring to the hand gesture she gave her husband, which was later depicted on the cover of The New Yorker with an infamous (and racist) cartoon cover depicting the Obamas as Muslim terrorists.

Reflecting on the hyper scrutiny she faced as a Black woman, the former First Lady clarified that sharing those experiences was not a “whining” about being in the public eye.

“I hope it doesn’t offend someone for me to tell you what happened in my life, because it is what happened to me, and it is the truth…if we don’t tell it, there will be other people who will try to pretend like it didn’t happen.”

Ultimately, Michelle Obama’s selection of Wu’s dress “changed his life,” she said. “That’s what we were trying to do with the choices that we made…change lives, to say something different about who belonged and who was good enough.”

Stylish but accessible

Though First Lady Michelle Obama is known for her extravagant gowns worn before foreign leaders and first ladies, and even the Queen of England, at most engagements with “The People” she made sure her fashion remained approachable and accessible.

“The thing about clothes I find is that they can welcome people in, or they can keep people away. And if you’re so put together and so precious that things are so crisp and the pin is so big, you know, it, can just tell people, ‘look, don’t touch me.’ Your clothes can make people push away,” said Obama.

“I always wanted to be able to, if a rope line was happening, if somebody was going to be in tears and need a hug, we’re not wearing white. We’re going to wear print if I have stuff to do…I’m not going to push somebody away when they need something from me, and I’m not going to let the clothes get in the way of that.”

While a First Lady’s style may be trivial to some, Obama knew as a woman, and a Black woman most especially, everything down to the heel mattered for a woman in politics.

“There had to be a lot of thought, and that stuff had to be done well in advance,” said Obama, who would have monthly fittings with her stylist Meredith Koop.

The accessibility and inclusiveneess of Michelle Obama’s style went beyond her clothes, but also in choosing her glam team, which was comprised of people of color, young people, women and men. The former first lady admitted her team didn’t get much recognition for their years-long work with her at the time.

“I always felt like fashion was the underlying story, so that meant that they had to kind of cut their shine,” she said. “We were also thinking about the times that we’re in. How are we going to talk about fashion when there’s a recession? How are we going to talk about, you know, a pair of shoes when, you know we need immigration reform?”

Messages behind “The Look”

Behind some of Mrs. Obama’s most beloved looks are stories once untold. The former First Lady jokingly shared with Wesley Morris that one of her most talked-about looks as First Lady — a shiny, rose-gold Versace gown that accentuated her curves — sent one simple message after serving many years under the public microscope: “Bye!”

“The Versace dress was the last state dinner [with former Italian Prime Minister Matteo Renzi and his wife, Mrs. Agnese Landini]. So that was a kind of, I don’t care,” said Obama. “I will tell you that one was like, because of the dresses that were available, that rose gold, I put that on. I was like, this is sexy. It’s the last one.”

Another iconic look from Michelle Obama came four years after she left the White House: her burgundy pants and overcoat fit by Sergio Hudson, worn at the U.S. Capitol for President Joe Biden’s inauguration on Jan. 20, 2021.

While the outfit was celebrated among fashion enthusiasts for its bold and powerful look, the former first lady said it was particularly chosen out of practicality—and, potentially, survival.

Just days before, the Capitol was violently attacked by angry rioters who had attended President Donald Trump’s “Stop the Steal” rally after he repeatedly lied about the 2020 election being “rigged” against him.

“I was really in practical mode. We didn’t know what was going to happen at this inauguration, because the sitting President was trying to convince us that January 6 was just a peaceful protest,” said Obama. “It wasn’t clear whether anybody was going to be safe.”

Normally, Mrs. Obama would travel with her entire glam team for “touch-ups” and staff assistants; however, given the safety concerns, she decided against it.

“I said, I don’t want anybody with me inside this perimeter, because if something pops off, I don’t want to put my team in jeopardy,” she recalled.

“I knew I wanted to wear pants because I was thinking, I have to run. I need to be comfortable…The boot that I wore was a lower heel. I wanted to be able to move. I wanted to be ready.”

Reflecting on the Sergio Hudson look itself, Mrs. Obama called him a “fabulous designer,” who was “known for his suits and his coats.”

“I put it on. I felt good in it. I felt warm,” she said. However, she admits, “I had no idea that was going to break the internet.”

Michelle Obama’s book, “The Look,” is now available from Penguin and can be found in all stores that sell books.