Advisors Drop The Wall Street Attire for a More Alternative Approach

The stereotypical advisor wears tailored suits, drives a luxury car and spends weekends working on their golf swing. Not anymore. 

While the traditional Wall Street persona still works for some, just like portfolio management, it isn’t one size fits all. For many advisors, the buttoned-up, country-club professional script can feel inauthentic, and authenticity is increasingly what clients want. “There’s a huge opportunity for planners and advisors to show up in a more raw, unpolished, slightly messy way,” said Philip Olson, co-founder of Solstice Wealth and host of the Two Cents PBS show. “So many clients are just starving for that.”

Heart on Your Sleeve Tattoo

Olson has arm sleeve tattoos, long hair, painted nails and he often wears cut-off t-shirts at the office. A self-described theater nerd who plays in a ’90s cover band, he’s open about his political and social views and is unapologetically casual with clients. “It becomes less professional and more personal,” he told Advisor Upside. “I’ve attended clients’ weddings and funerals. I consider that a huge honor and the way it should be, frankly.”

That approach isn’t for everyone, and that’s the point. His clientele skews more toward people with non-traditional gender, sexual expression and relationship models. “It’s people who generally feel disenfranchised by the mono culture that most ‘big finance’ gives,” he said.

The business itself has evolved, too. What was once largely investment management is now deeply rooted in financial planning. As retail and DIY investing platforms proliferate, clients need more than portfolio construction; they want connection. A 2025 report from advisor directory Wealthtender found that:

• Nearly 90% of clients’ reviews of their advisors centered on relationship quality, planning advice and emotional factors.
• Clients are nearly 25 times more likely to mention their advisor by name than the firm, highlighting just how important personal connection is in client-advisor relationships.

“We actually had a prospective client breathe a sigh of relief when he saw that my teammate sported purple dyed hair,” said Sam Mockford, a CFP with Citrine Capital. He admitted that he’d been putting off finding a financial advisor for some time because he loathed the idea of working with “a bunch of f****** suits.”

Make ‘Em Laugh. Humor can also help bridge that gap. Sean Williams, founder of Cadence Wealth Partners, sends prospective clients a welcome video parodying The Office and fills his team’s website bios with self-deprecating humor. His own bio describes him as a Marine, bald, moderately intelligent and a hater of closed-toed shoes. He even crafts welcome gifts in his woodshop for new clients.

“Ultimately, when we are representing our authentic selves, it builds trust with clients more quickly and lowers barriers to conversation,” Williams told Advisor Upside. “They see us as real people.”