Best Dressed Women 2011

Anyone who has ever been to a charity event with North Shore families knows that it’s easy to be stunned by all the gorgeous, stylish women living in our communities.

But what really makes some of these women beautiful is their generosity and commitment to supporting organizations that touch lives. For our Best Dressed issue this month, we asked five exceptional local women to open up their hearts as well as their closets.

Karen Gray
Lake Forest

A stylish blend of personality, looks, artistry and organizational skills put Karen Gray of Lake Forest at the top of modeling and advertising careers before she achieved philanthropic success as President of the Women’s Board of the Art Institute and the Boys and Girls Club of Chicago, Executive Committee member of Northwestern’s Women’s Board and Opening Night Gala Chairman of Lyric Opera’s Women’s Board. She is also a supporter of other worthy organizations including the Natural Resources Defense Council and Women In Need Growing Stronger (WINGS).

Her paid and volunteer work is as impeccable as her style.

Karen has raised great kids too. Her son, John, is a senior at Northwestern spending this semester in China and daughter, Allie, is a Dartmouth freshman.

Although Gray is now deeply embedded in Chicago’s civic life, she didn’t grow up here. She was an Ohio beauty who found her way to New York City’s famed Wilhelmina Models. Gray next worked in the Chicago advertising world, where she rose to be a vice president and creative director at Leo Burnett, winning awards for her work for McDonald’s and the Super Bowl, among other prestigious clients.

“I love Chicago!” Gray declares. “After 28 years, I am happy to call it home.”

Gray is youthful, well-rounded, big-hearted, classic. Her style is classic too. “Very tailored and simple, with often an addition of one special accent piece, for example a special shoe or piece of jewelry,” she explains.

“I’m old school with my favorite designers. Oscar and Valentino are difficult to beat.” She grins, “And I also love Chanel of course!”

Ann Waris

Ann Waris has been involved with Loyola Academy “forever.” That’s what happens when you’re a committed volunteer. She got involved when daughter Mary Cate, who’s now 25, started attending and continued through son, John, 21; daughter Eileen, 19; and the youngest, Clare, who graduated in May.

“It will be a change,” Ann admits with a laugh, as we talk about the family no longer having a student at Loyola. Among her many volunteer positions at the school, she’s worked on the Loyola Ramble, which is the big fundraiser, as well as girls lacrosse, which required a lot of parent involvement when it was a club sport.

Beyond her children’s high school, Ann is also involved at Misericordia, where her 51-year-old brother has lived for eight years. “It’s been incredible for him,” she says. “It has let him be as independent as he can be.”

She chaired the fashion show last April, which was a perfect match for her interest in style.

“I keep it pretty simple,” she says. “Since I’m petite, I shy away from big patterns.”

When talking about her style icons, she mentions Michelle Obama and Jacqueline Kennedy Onassis. She loves the classic style both women have taken and made their own. She admits that occasionally her daughters will talk her into a purchase: “I have to make sure the dress isn’t wearing me!”

Favorite designers include Kay Unger, Trina Turk, David Meister. “And I love Kate Spade!” she says. Her daughters saw her looking longingly at a particular Kate Spade bag and surprised her with it for Mother’s Day.

A fitting present for a mom who has been so devoted to her children, their school and her family.

Andrya Smith Pearson
Vernon Hills

Andrya Pearson, a mother of two teenagers and a marketing manager at Allstate, describes her style as “classic chic.”

“I love classic designs and colors, and highlighting my style with bold and fun accessories,” she says. “I try to have one accent point that really strikes—a shoe, a color, a purse … ”

She likes wearing black and white, or navy and white, and her favorite stores include White House Black Market, Nordstrom, Ann Taylor and Talbots.

When she’s not busy working and raising her two daughters, Andrya actively supports Midwest Young Artists, a full-curriculum, pre-college youth music school, with her husband, Patrick, who is the orchestra director at Oak Park and River Forest High School and a conductor for MYA.

“I’m an advocate,” Andrya says. She contributes by recruiting kids and attending events, among other activities.

The Pearsons, who have been involved with MYA for 16 years, also sponsor an underprivileged child through Young Music Scholars, a program that Patrick helped found, and they have been sponsoring a child in Kenya through the anti-poverty organization Compassion International.

Andrya, who gets some of her fashion sense from her daughters, is enjoying emerging from what she calls “the mom phase,” when all her clothes were just comfortable. She says, “They’re not spitting up on me anymore, so I’m rediscovering fashion, and my style.”

Theresa McCay Boutross

With her model-ish beauty and slender figure, you might think Theresa Boutross belongs on TV—and you wouldn’t be the first. In fact, Theresa was fired by Donald Trump on season five of the NBC’s “The Apprentice.”

“It was a joke,” the therapist and mother of two recalls of being on the show. The most exciting part was being selected, she says.

As for her personal style, Theresa aims for “classic simplicity, with an edge.” She prefers to shop on vacation in boutiques where she can find pieces that can’t be found anywhere else. At home, her favorite designers are Dolce & Gabbana, and Sergio Rossi and Giuseppe Zanotti for shoes.

Theresa practices marriage and family therapy at the Center for Intra-Spection, the private practice she founded, and, with her family, she supports no-kill animal shelters and adoption causes. She adopted both her son, 3, and her daughter, 1, after struggling with infertility for seven years. She’s currently working on a book about the experience, and looking for a publisher for a children’s book she wrote about adoption.

“I have the children I’m meant to have,” she says. “I wouldn’t change a thing.”

Deborah Jarol

Deborah Jarol serves on the Medical Research Institute Council of Children’s Memorial Hospital because, “every year you get to reinvent yourself.” She’s held numerous volunteer positions on the council, but what excites Deborah most is what might be next.

It’s a philosophy that also extends to her sense of style—interior design, gardening and fashion—she loves to discover the next thing.

“I consider my style up-to-date,” she says. “I was in Paris and saw a skirt from across the street. It only cost 30 Euros, but I knew it would be fabulous.” She’s wearing that skirt with a Chanel jacket and other couture pieces.

“If you have an eye for quality, you can mix and match, whether it’s flowers, cooking, or clothes,” she says.

Deborah has lived in Winnetka for about three years, having moved from nearby Glenview. Her children, Ashley and Bradley, have both launched their own careers. And Bradley is now on the Medical Research Junior Board Foundation of Children’s.

“The board is given phenomenal input,” she says talking about why she’s remained on the council for more than 12 years. “You listen to the doctors and decide who to fund based on what they want to do.”

Outside of her charity work, Deborah is a passionate baker who offsets her love of decadent carrot cake with an equal devotion to Zumba. Her other loves? Canyon Ranch Hotel and Spa in Miami and Neiman Marcus. “They offer a mix of designers. It’s so nice, they’ll help you put it all together,” she says.

She’s also devoted to Saks, and with the retailer, she hosted a Ralph Lauren Blue Label fashion show in her home for about 50 friends. “I don’t want retail to die,” she says. Because Deborah knows there’s an amazing skirt, hidden in a little shop, just waiting to be discovered.

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