WW CEO Mindy Grossman's Getting Dressed Mantra Is all About Feeling Good

The power woman's approach to daily power dressing is methodical—but that doesn't mean boring.

what i wear to work

(Image credit: Mindy Grossman)

WW CEO Mindy Grossman has spent several decades in the fashion business. With successful turns at companies like Nike, Ralph Lauren, Tommy Hilfiger, and Home Shopping Network, she knows a thing or two about passionate consumers and explains that a string of bold risk-taking— dropping out of law school, breaking off an engagement, and blindly moving to New York City from Long Island at the age of 19— got her to where she is today.

Years later Grossman's risk-taking is still reaping rewards. Straight off of Oprah Winfrey’s ‘2020 Vision: Your Life in Focus Tour’ which ended in March 2020, Grossman began leading a global company through a pandemic. She was forced to make tough calls, impacting millions of people, in real time. One of those decisions was to take WW fully digital, which she and her team did across 12 different countries, in only six days.

While her schedule is jam-packed with Zoom calls, speaking engagements, and events, connecting with herself has also been a top priority for Grossman. That means sticking to rituals, participating in family time, and setting up an environment where she can thrive. Here’s what she wears to tackle the busy work day.

What I Wear to Work

Grossman and Oprah Winfrey.

(Image credit: Mindy Grossman)

Her Morning Routine

I’m a fairly structured person. Pre-Covid I traveled 40 percent of the time, but that suddenly changed and we were permanently at home in our weekend place in Millbrook, New York. At the time, I didn't even have a work desk set up there. My daughter, her husband, and my two granddaughters were also living with us. Given the intensity of everything, I really needed to stick to a ritual.

Generally I wake up at 5:30am, put on the coffee, and print out the New York Times' crossword puzzle. My husband and I have a contest to see who can finish it faster. Then, I consume a very broad cross section of media in the morning—everything from Forbes to fashion. I lay out my clothes very methodically based on my schedule, get dressed, and head downstairs for breakfast.

What I Wear to Work

Grossman at home in Upstate, New York.

(Image credit: Mindy Grossman)

On Getting Dressed:

There are a few things I think about when I’m getting dressed in the morning: What am I doing? Who am I meeting? What do I want to convey? Ultimately, though, I want to feel good about myself. You’ll never see me in sweats. Did I swap my heels for a fun Gucci sneaker and throw on some jeans while working from home? Yes.

My wardrobe is a combination of statement pieces and classics. I like to mix and match new and existing pieces to create outfits that are personal to me—I’ll never buy a look from the runway.

On Her Favorite Designers:

I love Alexander McQueen—my favorite piece is their leather peplum jacket. I can pair it with everything: a pencil skirt, black pants, boots. I just bought a new McQueen suit. The jacket has jeweled heart sleeves on them. I'm getting excited about shopping again.

In late November, I attended UNICEF’s Gala at Lincoln Center as a board member and bought a Dries Van Noten cocktail dress to wear along with “UNICEF blue” satin and bejeweled Balenciaga pumps. I love a statement accessory. I also happen to love a good leopard-anything.

what i wear to work

Grossman at the WW office in Manhattan.

(Image credit: Mindy Grossman)

On Family Time:

My daughter and I are both very passionate cooks. I would say I'm very good, but she's chef quality. Cooking together became our ritual. It’s a moment to relax. Even if I have to go back to work after dinner, it provides a nice break in the day. You have to find the moments that force you to disconnect or you'll never shut off your work-mode mentality.

On Her Style Evolution:

I’ve gotten more confident over time. I gravitate towards pieces that fit where I am at this point in my life and those are a lot different than when I started in this business.  I love to shop online at sites like Net-a-Porter, Farfetch, and Saks Fifth Avenue. My return rate is pretty low. The reality is that over time I've gotten a pretty good sense of myself and know what's going to work for me.

Shop Some of Mindy's Favorite Pieces:

Sara Holzman
Style Director

Sara Holzman is the Style Director for Marie Claire, where she's worked alongside the publication for eight years in various roles, ensuring the brand's fashion content continues to inform, inspire, and shape the conversation about fashion's ever-evolving landscape. With a degree from the Missouri School of Journalism, Sara is responsible for overseeing a diverse fashion content mix, from emerging and legacy designer profiles to reported features on the influence of social media on style and seasonal and micro trends across the world's fashion epicenters in New York, Milan, and Paris. Before joining Marie Claire, Sara held fashion roles at Conde Nast's Lucky Magazine and Self Magazine and was a style and travel contributor to Equinox's Furthermore website. Over her decade of experience in the fashion industry, Sara has helped guide each brand's style point of view, working alongside veteran photographers and stylists to bring editorial and celebrity photo shoots to fruition from start to finish. Sara currently lives in New York City. When she's not penning about fashion or travel, she’s at the farmer’s market, on a run, working to perfect her roasted chicken recipe, or spending time with her husband, dog, and cat. Follow her along at @sarajonewyork