Unveiled in February, the official portrait of Michelle Obama is striking in its entirety, but there’s one element that undeniably dominates the life-size canvas: that dress.
The mostly white, halter-style piece is complicated and unexpected, and such a striking departure from the traditional gowns and pantsuits of the past that it immediately spawned think pieces on its symbolism. There’s much to dissect: the geometric pattern, at once traditional and modern, reminiscent of both Gee’s Bend quilts and a forward-thinking minimalism. With pockets and a sweeping skirt, it’s somehow both humble and regal, too, not unlike like the First Lady herself. Artist Amy Sherald’s creation “overemphasizes an element of couturial spectacle,” the New York Times wrote, “but also projects a rock-solid cool.”
So, yes, the dress was a scene-stealer. And the woman behind it, forever immortalized in the National Portrait Gallery (she had no idea that was going to happen, by the way) is Michelle Smith, founder of the New York City-based contemporary women’s brand Milly. In an appearance at Tootsies last week, Smith gushed over Obama, who the notably political designer confirmed is her favorite person to dress. Though it was a bespoke creation, the portrait gown was based on a design from Milly’s spring 2017 collection; Smith has since removed it, insisting “it’s for Mrs. Obama only.”
Obama’s closet contains more Milly than just the dress, though: she was photographed in a Milly blouse on her last day in the White House, and Smith revealed last week that she’s also a fan of the label’s much-loved Natalie pant. The $395 wide-leg, true-waist pant made from Italian Cady fabric is a top-seller, Smith told the crowd gathered at Tootsies for a private presentation of the bright, whimsical new collection. “It’s been photographed on J.Lo,” Smith said of the Natalie. “She actually bought it in the store, believe it or not. Michelle Obama and a lot of amazing and inspiring women have this pant.”
Beyoncé and Cindy Crawford are known Milly fans, too. But long before Smith was dressing luminaries, she was just a kid with a dream. At 11, she set her sights on New York’s Fashion Institute of Technology, much to her parents’ chagrin. “They wanted me to go to a traditional university and get a well-rounded education,” she said. “But I was really persistent, and I won the battle. Luckily it worked out for me.”
Once she made it to FIT, she folded sweaters at the Gap to help pay for it. Obsessed with the luxe Hermes bags she saw in magazines, she landed a part-time sales gig there and, at 18, became the youngest employee at the high-end French fashion house. Dreaming of Paris, she wrote to the president of the company requesting an internship. She got that, too, and was the first American employee sent to HQ.
Three months in Paris turned into three years, during which she worked for other legendary fashion houses like Louis Vuitton and Christian Dior Haute Couture. Smith’s experience with European luxury goods largely informed her own collection. With the launch of Milly in 2000, Smith was an early arrival to the contemporary landscape, blending athletic silhouettes with traditional ready-to-wear. The field is saturated now, but Smith stands out among the pioneers.
Her latest collection is “a reflection of [her] entire background,” Tootsies senior buyer Leah Little Hale remarked. “Your love for color, for design, for incredible fabrics, which is one of the reasons as a buyer that I continue to be in love with this brand.”
Milly’s fall collection is indeed rich with color, a veritable rainbow of shades: emerald green, vivid magenta, vibrant marigold, all drenching everything from suit jackets to cocktail dresses. “It’s all chromatic,” Smith said, “and it’s about head-to-toe dressing in the same color, or shades of the same color, and really harnessing the power of that color.”
Head-to-toe cream, she said, signifies purity and sends a powerful message—and forget that antiquated post-Labor Day “rule;” Smith is all about winter white. Red, of course, means passion; cobalt blue and navy convey honesty and trustworthiness; yellow emanates positivity and happiness, and pink—well, pink is mostly just fun, particularly in the form of one outrageously fabulous faux fur coat paired with a buffalo-check plaid mini skirt.
“The message in the show is that when all of these beautiful colors come together, they form a rainbow,” Smith said. “So there was a message of equality. Everyone’s welcome in the house of Milly.”
Hale has long kept Tootsies stocked with key Milly pieces, but her devotion to the brand goes beyond that—the buyer swears by the label in her personal life, too. She recently wore the red satin pant suit to a wedding and “felt great,” she declared.
“That’s what I want. I want people to feel great—amazing,” Smith said, noting “everything stretches; comfort is so key.” She tries everything on herself throughout the design process in her studio, too. “If I feel amazing in it, it gets in the collection. Not so amazing, we cut it. And I think because I’m a female designer, I’m sensitive,” she added. “Can I drive? Can I do these things in this dress? It’s really merging beauty and practicality.”
Smith’s mission of “merging beauty and practicality” is unchanged whether she’s dressing Beyoncé or a 9-to-5er. “I love what I do, and I love dressing women,” she said. “I really want women to feel beautiful and empowered and inspired every day—that’s my goal. I hope I’m doing a good job almost 20 years later. I’m trying every day.”