Michelle Obama's Best And Worst Looks As First Lady

Michelle Obama's eye for fashion and style has evolved over the years. Nowadays, the former FLOTUS has chosen a more daring approach and sometimes wears outfits that suggest she is desperate to stay on trend. She traded her touched-up bobs for braids and switched up her look to include striking, statement-making pieces, such as sequin thigh-high Balenciaga boots that broke the internet. Just as she makes headlines these days, Michelle's wardrobe was captivating to the public during her time as First Lady.

After Barack Obama was elected into office in November 2008, it didn't take long before the masses' obsession with Michelle's outfits showed itself in the stock market. According to a 2010 ABC News report, Michelle obviously worked with designers that made her some stunning ensembles, but her preference for off-the-rack clothing by apparel brands such as J.Crew and the Gap was the real game-changer: It propelled their revenue into the billions.

"Each single appearance of hers could move a stock price by $14 million," David Yermack, a professor of finance and business at New York University's Leonard N. Stern School of Business, revealed in an interview with Good Morning America. The former First Lady sported many eye-catching looks during her reign, but sometimes, she fell short of the mark. Here's a roundup of her hits and misses.

Following Barack Obama's inauguration in January 2009, he and Michelle Obama were honored with not one, but 10 official inaugural balls. The magical evening full of dance and music included a serenade by 35-time Grammy Award-winner Beyoncé Knowles, and as Barack looked put together in a sleek monochrome tuxedo with a white bow tie, Michelle was dolled up in a one-shoulder gown by designer Jason Wu.

The spectacular silk-chiffon number swept the floor and featured gathers at the waistline that gave it a flowing appearance. The cherry on top was a head-to-toe display of delicate organza flowers with crystal detail. Michelle accessorized the outfit with dangling silver earrings and a layered bracelet set, and crowned it with a pair of open-toe white heels.

Michelle's choice was not only a big fashion moment but also a statement on inclusivity. "Big-name designers tended to dress the First Lady for inauguration. I was pretty clear that I wanted to change that up," she explained in a chat with Vogue. "Jason Wu's story meant a lot in this moment — Canadian, Taiwanese, gifted, young — he must have been in his twenties at the time." The iconic number would eventually get displayed at the National Museum of American History, and the duo has since collaborated on other projects (details on this later).

As First Lady, Michelle Obama wore some amazing one-shoulder numbers that often turned heads. Case in point: When she attended the Congressional Black Caucus Foundation's 42nd Annual Phoenix Awards dinner in September 2012, she looked effortlessly gorgeous in a pleated black Michael Kors gown that accentuated her toned arms. She'd worn the dress twice in public, and both times, the former FLOTUS appeared to be at ease.

The same could not be said for when Michelle showed up to a May 2010 state dinner in honor of former Mexican President Felipe Calderón and his wife, Margarita Zavala. Michelle's dress, a one-shoulder shimmery purple gown by designer Peter Soronen, was attention-grabbing from a distance. The look featured head-to-toe pleats and a silver band, and Michelle accessorized it with teardrop-shaped earrings. 

When choosing clothes, Michelle often prioritized comfort. She told People that her outfits "had to be ready for the moment," whether she was gardening or doing jumping jacks with children. The entire ensemble came across as elegant to the untrained eye, but anyone with fashion-forward instinct could see that its neckline pressed hard against the former First Lady's skin. The look sacrificed Michelle's preference for comfort, since tight clothing can restrict movement.

Former President Barack Obama delivered his final State of the Union address in January 2016. Per usual, former First Lady Michelle Obama was in attendance, and her viewing box featured appearances by high-profile guests like Microsoft CEO Satya Nadella and former Connecticut governor Dannel P. Malloy, as well as honored small business owners. Michelle made headlines for standing in solidarity with victims of gun violence by leaving the seat next to her empty, and just as her stance was intriguing, her penchant for impeccable formal wear continued.

The previous year, Michelle had shown up for the State of the Union address in a textured zip-up Michael Kors skirt suit, and her 2016 look – a marigold dress by designer Narciso Rodriguez — had her trending online. The perfectly fitting number featured an elevated v-neck neckline and belt-like waistline threading, and, in many ways, its lack of sleeves was a reminder of Michelle's first official White House portrait (and it flaunted Michelle's most controversial asset, her bare arms).

Michelle's arms made for a heated topic when that first photo was published, but this time, the public was more gentle. One impressed fan wrote (via WFAA-TV), "Michelle Obama just brought fire with that DRESS!" In fact, David Yermack's research was vindicated in real time. The dress was sold by Dallas-based Neiman Marcus and originally retailed for $2,000. It was on sale for $628 when Michelle wore it, and by the time Barack had finished his speech, it had flown off the shelves.

The Asia-Pacific Economic Cooperation (APEC) summit was held in Hawaii in November 2011, and naturally, former President Barack Obama and Michelle Obama were in attendance as the hosts. Michelle put together a spouses luncheon at Kualoa Ranch, during which she reflected on her family's history with the island (Barack was born in Hawaii, and the then first family made a point to travel there at least once a year).

When it comes to fashion, Michelle looked effortlessly beautiful in a sleeveless midi dress with vibrant yellow tones and flower patterns, a true representation of the spirit of Hawaii. However, the look was a far cry from the outfit she had previously worn during the APEC leaders' dinner: a knee-length dress with rumpled fabric. The former First Lady's look lacked cohesion and featured a folding off-shoulder diagonal neckline in baby pink fabric that appeared to have been threaded in haste.

The bodice of the dress was just fine, but it was separated from the bottom half by a beaded band that suggested amateur workmanship. Overall, the ensemble violated the three-color rule since some tones were close in shade but not identical. Michelle's accessories also added to the chaos; she wore a pair of two-tone drop earrings with white accents and donned a broad bracelet with reflective hues.

Former French President Francois Hollande paid a state visit to the United States in February 2014, the first such visit by a French president in nearly 20 years. Hollande was honored with an arrival ceremony at the South Lawn of the White House, and as Barack made his exit when the ceremony came to an end, he was joined by former First Lady Michelle Obama, whose striking red coat-dress was hard to miss.

By all means, Michelle's look perfectly matched the winter season. The long-sleeved number featured a V-neckline with folded fabric, and its clearly visible stitch lines reflected meticulous craftsmanship. The lower half of the knee-length dress opened into a flare, giving it a sophisticated but chic effect. Michelle completed the look with a pair of leather gloves and a set of matching knee-high boots, all of which affirmed her refined taste.

That didn't mark the first time the former FLOTUS had pulled off such an elegant aesthetic. During Barack's second inauguration as president in 2013, Michelle looked stylish in a checkered coat-dress by award-winning menswear designer Thom Browne. That, too, had an A-line design that featured pleated detail, and Michelle topped off the ensemble with a pair of purple gloves and black velvet-leather boots.

In April 2009, former President Barack Obama embarked on a trip to Europe that saw him attend the NATO Summit in France. Upon arrival, the former first couple exchanged niceties with the then French President, Nicolas Sarkozy, and his wife, Carla Bruni-Sarkozy, and as usual, Michelle Obama's impeccable taste in fashion couldn't go unnoticed. The former FLOTUS donned a knee-length black and fuchsia coat by Thakoon, while Carla made a statement in a suede Christian Dior coat-dress with a bow.

Although Michelle's outfit made for a good choice in that moment, that was not the case when she joined the spouses of other NATO member state leaders on a tour of Rohan Palace and the Notre-Dame Cathedral the following day. Carla, for instance, rose up to the occasion and wore a black shirt and pants combo, which she paired with a well-tailored purple trench coat. She enhanced the ensemble with a timeless deep purple Chanel bag and low-heeled close-toe pumps.

Michelle, on the other hand, showed up in a low-effort, monochrome pants and blazer combo. The textured waist-length number featured a wide collar and had a chic feel, but Michelle's decision to wear doll shoes gave the outfit a laid-back touch. Coupled with a lack of jewelry (except for a pair of button earrings), it was as if Michelle was in a rush that morning and picked whatever was within reach.

The re-election of former President Barack Obama in 2012 called for a celebration at his official inaugural balls the following year, and the January 2013 night was as much a political affair as it was a night of fashion. Once again, Barack stuck to the basics and donned a tuxedo and a white bow tie (it wasn't so bad a move, as his 2009 outfit by Chicago-based clothier Hart Schaffner Marx was heavily in demand after the events).

Michelle made yet another stylish impression in a ruby-colored Jason Wu number. The long-length velvet gown featured glossy patches and crisscrossing straps reinforced with diamond-encrusted support. As the first couple was serenaded by EGOT winner Jennifer Hudson, it didn't take much fashion expertise to notice the gown's dramatic plunging V-back. When it comes to accessories, Michelle kept things simple by wearing a layered bracelet on her left arm, and, of course, her fringed and layered hairstyle did most of the talking.

The dress later earned its place at the National Museum of American History, putting a stamp on the Michelle-Wu duet as an outstanding creator-muse fashion collaboration. "I was like, 'Wow! She looks exactly like how I imagined she would look in that dress,'" Wu expressed in an interview with CGTN. "And that's the best feeling a designer could want...not to only create beautiful clothes, but somebody who can wear it to...the best of their ability."

As First Lady, Michelle Obama knew how to rock a ballgown, often characterized by its fitting upper part, a defined waistline, and a voluminous skirt. This was the case when Michelle and Barack Obama showed up to the Phoenix Awards Dinner at the Walter E. Washington Convention Center in September 2016 in a strapless Neem Khan gown with a sweetheart neckline. The golden dress featured carefully crafted stitches that created elegant gathers, highlighting excellent craftsmanship.

The opposite was true for a Carolina Herrera gown Michelle wore when she and Barack hosted a state dinner in honor of former French President Francois Hollande in February 2014. The long-length number featured a wide purple bottom, a black velvet waistline band, and a lacy upper half. Michelle wore her hair in a layered brown style and accessorized the look with a pair of large black drop earrings. 

The ballgown appeared stunning from various camera angles at first glance, but a closer look at the details revealed otherwise. It was decorated with stitches that traced the fabric to open into gathers, and although the designer's intention may have been to create a uniform spread, it ended up with pleats that had awkward protrusions. The general feel was that the fabric didn't complement the design as well as it could have.

Former President Barack Obama and his wife, Michelle Obama, paid a state visit to the United Kingdom in May 2011. Michelle looked stunning in various outfits, including a purple knee-length dress she wore on arrival and a mint-colored skater dress that she paired with a mini pink coat. But she truly turned heads in a floor-length Tom Ford number. The breathtaking white gown featured a crisscrossing halter neckline, a bow, and gatherers that hung in soft, flowing folds.

Michelle paired the gorgeous look with a set of white elbow-length gloves that stole the show, and at the time, the former First Lady's only concern was whether she needed to take them off during dinner. "Let me tell you, those were leather gloves that it took three people to put on," Michelle explained in her chat with Vogue. "Once they were on, I'm like, 'They're not coming off.'" Luckily, the late Queen Elizabeth, who always wore gloves during most royal engagements, advised her to keep them on.

That didn't mark the last time Michelle and Tom Ford collaborated on a stylish ensemble. During a 2018 appearance on "The Ellen DeGeneres Show," Michelle donned a pair of high-waisted black pants that she styled with a striking white top with an off-the-shoulder neckline. Michelle's off-the-shoulder looks can sometimes come across as flirty, but this post-White House number had a formal tone that she crowned with minimalist jewelry.

Michelle Obama has had her fair share of fashion blunders, but none caused as much of an uproar as the time she was pictured exiting Air Force One in a pair of Bermuda shorts. The former First Lady was in the company of her family at the Grand Canyon National Park Airport during a vacation. Michelle paired the shorts with a white tank top and a checkered pastel shirt, finishing off the look with sunglasses and a relaxed hairstyle. (Sadly, the real reason Michelle straightened her hair as First Lady was to avoid conflict.)

The rest of the Obamas' outfits were just as laid-back; Malia and Sasha Obama were both dressed in shorts and tank tops, while Barack wore a casual t-shirt and pants combo. The ensuing outrage sparked a debate over what constitutes an appropriate outfit for a First Lady while on holiday. Some critics suggested that a pair of linen pants would have suited the occasion better and shown more respect towards the presidency. At the time, Michelle stayed mum on the subject, but she later termed the moment as one of her greatest fashion missteps.

Although some of Michelle's inappropriate outfits have betrayed her relatable persona, she actually put much thought into what she would wear. The former FLOTUS had taken the hot temperatures into consideration, analyzed the fact that a dress wasn't a suitable choice, and made plans for an afterward engagement. "I eventually opted for the thing that felt mostly me, and it was the Bermuda shorts," Michelle recalled on the "IMO" podcast. "Because if we're going on a hike, this is how a normal person would go on a hike."