Are These Stylists the Secret to Leveling Up Your Career?

A 26-year-old woman moving to Silicon Valley for a tech job “can’t figure out what the hell to do with her style." The chief of staff to a Very Important Person in the Bay Area needs “a wardrobe that aligns with who she is professionally." A chief marketing officer at a $7.5 billion-valued company needs “a complete image revamp to give her more of an edge at work." These are some of the many client emails that arrive in Victoria Hitchcock’s inbox from women looking for help with simply getting dressed.

Hitchcock is not a regular image consultant for hire. The founder of Victoria Hitchcock Style specializes in helping high-powered women find what works for them, sartorially speaking. "I remember sitting in boardrooms and watching presentations from people at companies like Bank of America, Charles Schwab, and Sprint and thinking, 'God, these people are so brilliant, but they look horrible,’" she explains. "They're uncomfortable with this personal, holistic aspect of who they are, and don’t know how to dress themselves because of it.”

Offered quarterly or year-long with a minimum spend of $2,000, a membership with Hitchcock is essentially a boot camp on the old adage of “dressing for the job you want.” Clients leave with a wardrobe refresh designed to supercharge their confidence, and in turn, their career. Case in point: Peggy Alford, who climbed the ranks at PayPal to become EVP of global sales and currently sits on the board at Meta. Hitchcock helped Alford realize she “actually likes some flash and bling;” that gives her a boost in the boardroom even.

Hitchcock is part of an in-demand cohort of stylists treating a woman’s quest to find her professional style as serious business. Services offered—according to Jenny Corona, head of Moda Operandi’s executive styling program, Moda Private—include answering a client’s calls in the middle of the night when she’s speaking on a panel in Japan. Memorizing a CEO’s calendar and cataloging looks on a Chanel runway for a summit six months away. It means sourcing one-of-a-kind vintage Hermès Birkin bags and coordinating with fashion houses for the right haute couture gown for a fundraising gala.

The need for corporate image stylists has surged since the pandemic, which complicated the already challenging problem of what’s considered “work-appropriate.” Remote and hybrid work models blurred the boundaries between the office and home, the professional and the personal. As a result, countless women feel at a loss with their work wardrobe and need guidance from a pro when getting dressed.

In corporate speak, they’re looking for “a personal brand.” Establishing one can be the path towards a pay bump, explains Cassandra Sethi, founder of the New York City-based bespoke styling company Next Level Wardrobe. “Once you get to higher corporate and executive levels, it’s not just your work being promoted; it’s the holistic package of who you are,” says Sethi, whose styling services ring in at $6,500 for a virtual session and $15,000 for in-person. The sooner you start, says Hitchcock, the better your odds at playing the long game with your career: "A 26-year-old client recently came to me and said, 'I already foresee that how I build my presence now is going to take me to where I want to go,'" adds the stylist.

Clothing has long been a core tenet of professional identity. Steve Jobs had his black Issey Miyake turtlenecks. Elizabeth Holmes wore similar sweaters to emulate the late Apple CEO. Mark Zuckerberg’s gray hoodies and schlubby T-shirts from Facebook’s early days spawned a fashion archetype for male tech-bros. (Today, however, the Meta CEO is primarily in quiet luxury labels, cashmere tees without coffee stains, and Cuban link chains—likely a rebrand orchestrated by a covert corporate stylist to align with his entry into the Broligarchy.) Other industry bigwigs straddle the C-suite and high-fashion sector: During Marissa Mayer’s stint as Yahoo CEO, Vogue called the tech exec “an unusually stylish geek,” citing her penchant for Yves Saint Laurent stilettos, Oscar de la Renta knits, and Carolina Herrera cocktail dresses.

But starting from scratch to build a professional-slash-personal brand isn’t easy in a post-pandemic landscape, where office dress codes have stretched to allow for elastic-waist soft pants and Allbirds sneakers. Dressing for the workplace has never been easy, full stop: Women working in male-dominated fields have long been told to follow a formula that makes them fade into the background. No bright colors. No distracting jewelry. Nothing that will make them stand out—the fact that they're women already makes them too different.

But the winds of change have impacted workwear. With women increasingly rising to leadership roles and fashion trends becoming more fluid en masse, gone are the days of souped-up-shoulder pads to mimic the men in the C-suite; gone are cookie-cutter pantsuits; gone, for the most part, is a prescriptive idea of professionalism in general. It’s no longer about blending in. It’s not about “borrowing from the boys.” “In 2025, it’s about 'stealing it from the boys, making it your own, and finding whatever you feel comfortable in,’” says stylist Danielle Cafiero, who pivoted to professional fashion consulting post-pandemic to help her clientele navigate the new normal of business dressing.

And along the way, power starts to look different. A VP’s presentation pops even more because her Cartier watch makes her feel like a powerhouse. A fintech founder is more at ease in loose trousers and a silk blouse than the tightly-tailored girlboss power suit she thought she needed. A CMO finds that reasonable kitten heels boost her self-esteem more than six-inch stilettos ever did.

“My job is being a confidence pusher,” says Evonya Easley, an Atlanta-based stylist for executive professionals, including biomedicine billionaires, entertainment titans, and too many Fortune 500 founders to count. “I'm not performing the heart surgery—but I'm dressing the heart surgeon. And just maybe she does better work because she feels confident about what she wears when she takes off her lab coat and scrubs."

Because getting dressed for work has always been about so much more than just clothes. “Deep down, the women I work with truly don't feel like they deserve their position and think someone will realize they shouldn't be there,” says certified image consultant and neuro-coach Melanie Lippman. “They’re approaching their wardrobe the same way: they’re fearful and scared of making a mistake, so they don’t take any risks.” On the other side of their imposter syndrome is what they’ve wanted all along: a professional style that amplifies their power and purpose.

Take Rebecca Yang, a tech leader and former U.S. diplomat. “Throughout my career, I've often been the only woman, the youngest, or the only person of color on my team or organization, and more often than not, all three,” she explains. “I've often had to justify my existence and prove myself, often to my own detriment.” After hiring Hitchcock, the two worked on accessorizing, developing custom outfit lookbooks, and curating a closet that reflects Yang’s courage. Now, she says, “my personal brand reflects the authentic leader I have been all along.”