Chatting with Our 2019 Women of Style

Meet this year’s women of style—five dynamic fashionistas who combine classic looks with forward-leaning flair.

Blouse and bow by Saint Laurent, pants by 16Arlington, earrings from Ikram and Maria Tash, shoes by Manolo Blahnik.

Ceta Walters
The fashion mix master showcases style through her blog, Clark and Stone.

After a few years as a stay-at-home mom, Ceta Walters made it her mission to find out who she was. “I started dating myself again,” she says. “I started working out and eating better... and when I began to feel good about myself is when I fell in love with fashion again.” Her passion reignited, the former model launched Clark and Stone, a lifestyle and fashion blog that, in less than three years, has garnered more than 50,000 followers on Instagram. Each post is an ode to her “classic, edgy and a little boho” style, showcased in labels like Chanel and Givenchy (all perfectly tailored by Boguslaw). Walters picks up pieces at local spots like Ikram and VMR, and has been known to purchase couture directly from high-end rental shop By:Fashionaholic when she just can’t give it back. Her looks are curated down to the accessories: She prefers fine jewelry and never leaves home without an earful of Maria Tash studs. This season, she sprung for a metallic Chanel boy bag from Karl Lagerfeld’s last collection for the brand—and last season, it was all about a pair of knee-high Isabel Marant Denzy cowboy boots. “I couldn’t get those boots out of my mind the month they launched—and I’m a size 41, so I have to pull the trigger right away,” Walters says. “I always say, nothing haunts you like the things you didn’t buy.”

Styling by Henri Trinh with Option 1 Artists; on-set Hair & makeup by Ashley Rike with Option 1 Artists; walters’ makeup by Delisa Lee; artwork: Untitled, William McLure (2019, oil and charcoal)

Painted dress by Sarah Raskey Fine Art, earrings by Chanel, vintage bracelet and ring.

Sarah Raskey
This artist and licensed psychotherapist combined two disparate fields into a passionate career.

“I like the idea that fashion is an extension of who we are, what we feel and how we communicate with others,” says Sarah Raskey, an artist who loves to create in many mediums, including clothes. “I like to be an out-of-the-box thinker when it comes to my attire.” Indeed, Raskey came to our photo shoot with some gorgeous pieces, but by far the most stunning were two dresses that she had created and painted. “When I make my pieces now, I try to create something that has a relentless allure,” she says. “That’s where I try to take things in my work as an artist, and I hope to expand on that more.” For inspiration, Raskey likes the British house Alexander McQueen, which is now headed by Sarah Burton, and Dutch fashion designer Iris van Herpen, who has dressed the likes of Lady Gaga and Tilda Swinton. “I have name brand and designer items in my collection, but all that really matters is that I think it’s cool,” Raskey says. “I try not to pay too much attention to what people think is trendy.” In her private therapy practice, Raskey has found her artistic abilities to be a boon to her clients. “I work with a lot of creatives: artists, musicians, people who benefit from creative outlets,” she says. “I find, when we don’t have words to say, we can use imagery.”

Artwork (in mirror): “Crescent Panel Diptych” by IMG (2019, acrylic on canvas)

Dress by Diane von Furstenberg, shoes by Brian Atwood.

Gabrielle Martinez
Color and culture are the inspiration behind this brand marketing exec’s global style.

Gabrielle Martinez’s Mexican heritage inspires nearly everything she does—and getting dressed in the morning is no exception. “When I was young, it was impressed on me how we present to the community,” she says. “Even though we had very little means, we were always polished when we walked out that door; that was important to my parents.” Now, in her role as co-founder and managing partner at Agency EA—a brand experience firm that has worked with clients from the Obamas to Oprah—creativity is key. Her style is a conglomeration of cultures and colors—she’s been obsessed with the ornamentation of mariachi musicians since she was young—and usually anchored by sneakers (she has more than 60 pairs, including a handful of custom creations from Leah Kirsch). “I’m always trying to buck convention and get something off the beaten track,” Martinez says. She finds RSVP Gallery an easy place to do that in Chicago, but mostly looks beyond the city limits: Kith and Bergdorf Goodman in New York, Forty Five Ten in her hometown of Dallas and the new Faena Bazaar in Miami Beach. She follows up-and-comers like Melody Ehsani, a streetwear designer out of L.A., and opts for artisan-made accessories to pepper into her wardrobe of staples from Diane von Furstenberg and Oscar de la Renta. “And I’m obsessed with Rosie Assoulin,” Martinez adds. “She’s on another level in terms of drama and flair.” Seems like a match made in fashion heaven.

Makeup by Shannon O’Brien

Dress by Zara, shoes by Giampaolo Viozzi, vintage earrings.

Roopa Weber
As the newly appointed chief marketing officer of Ariel Investments, this executive uses fashion to project her confidence and professionalism.

Although she sits in a C-suite office at one of the city’s top investment firms, Roopa Weber dresses with flair that’s seldom associated with finance. “We’re a culture of independent thinkers, which comes out in how we dress, how we invest and how we put ourselves together,” says Weber, who credits Ariel Investments co-CEO and president Mellody Hobson with establishing that culture. “As a woman who is as smart as she is beautiful and put together, Mellody sets the tone from the top, and she lets people’s individuality come out.” For Weber, that means a look she describes as professional chic. “I try to throw in something interesting and funky, usually through accessories or shoes,” she says. Weber’s favorite Chicago boutiques include P.45 and Intermix. And she adds, “Ikram is great for finding up-and-coming designers. Plus, they have amazing alterations.” Weber supplements her core wardrobe with unique vintage pieces she finds at the Randolph Street Market and when traveling. It’s just one of the ways she has fun with her look. “Fashion has given me so many opportunities to connect with people,” she says. She serves on the School of the Art Institute’s Fashion Council, and was selected to be a member of the Vogue 120, which recognizes style leaders. “It introduces you to people from different walks of life who share your interests.”

Dress by Mira Couture, necklace and earrings by Harry Winston.

Caylei Vogelzang
The businesswoman and editor brings a fashion-forward attitude into the workplace.

Beginning with her days staging fashion shows of thrift store finds as a kid in southern Oregon, Caylei Vogelzang has had a passion for fashion for as long as she can remember. Now the director of business strategy at Vogelzang Law and the editor-in-chief of Cancer Wellness magazine, she has seen her style shift toward conservative yet ubertailored suiting and well-made dress shirts. “My style has certainly changed throughout the years,” she says. “I am less flamboyant in some ways—and more flamboyant in others.” Case in point: her affinity for fabulous lingerie and love of hats. (“I don’t know why more people don’t wear them.”) Fashion is more than just clothes for Vogelzang, though: “It’s armor to empower you even on the trickiest days... and empowerment is much easier to attain in beautiful pumps.” She’s a Neiman Marcus junkie, but also frequents a host of “usual suspects,” like Ferragamo (for wear-all-day work shoes), Hermès (for always-vibrant scarves), Prada, Max Mara and Chanel. She accessorizes with custom pieces from jeweler Jamie Erlien (like the white-and-yellow diamond sparkler that was a 10th anniversary gift from her husband) and Harry Winston. On her jewelry wish list: “A fabulous zipper necklace from Van Cleef & Arpels and a bejeweled Serpenti watch from Bvlgari.” She’ll surely acquire them soon, but don’t call them splurges. “I really do not use that word,” she says. “I prefer ‘self-care through adornment.’”

Vogelzang’s Hair by Emilio Rivera at Salon Duo; makeup by Reyes Almanza using Hourglass Cosmetics; artwork: ”Swirl in Grey” by IMG (2019, acrylic on canvas)