How Financial Adviser Phil Serra Dresses Like a Million Bucks

Phil Serra, a financial adviser with Merrill Lynch, talks his fashion sense and what he loves about Detroit.
Serra wears a look purchased, head-to-toe, from Cicchini Custom Clothier in Birmingham — including a sports coat that he calls his “Frank Sinatra jacket.” // Photograph by Sal Rodriguez

The year is 1989. Phil Serra, who is in his mid-20s at the time, has just taken on a new role as an account executive at Merrill Lynch, the wealth and investment management division of Bank of America. Naturally looking to dress for success at his brand-new job, the Detroit native decides to use one of his first paychecks to buy a single-breasted blue suit from Cicchini Custom Clothier in Birmingham.

Thirty-four years later, the 59-year-old West Bloomfield Township resident is still going strong at Merrill, where he has risen to become a wealth management adviser, as well as managing director of his own team of advisers under The Serra Group.

In this position, he helps clients set and meet goals, “whether it’s securing a mortgage on a new house, getting a line of credit for business, or helping the next generation get started with budgeting and financial planning,” he says. Serra also serves as an ambassador for Better Money Habits, a free finan- cial education platform from Bank of America, through which he promotes financial literacy at local schools.

To this day, Serra buys all his dress clothes from Cicchini, crediting the late founder, Paul Cicchini, and the shop’s team for keeping him sharp over the past four decades.
Here, Serra talks about all things suits and more.

My personal style is …

Business chic. [My style] has gotten a little less formal, but I still wear a tie. I’m rarely without a vest; with all my suits I wear to work and to client dinners, I usually include a customized vest.

What’s your all-time favorite look?

I call it the “Frank Sinatra jacket” — I’m 100-percent Italian and absolutely obsessed with Frank Sinatra music. It’s a red sports coat with a subtle, black checker print that I got about 10 years ago. I wear it a lot. I like to pair it with a nice pair of black slacks and a coordinating red vest.

I can’t leave the house without …

A pocket square in my sports coat. And a great attitude to start the day!

On experimenting with colors and prints:

I left public accounting to pursue a career on Wall Street, and I wanted to have conservative colors. I started with a lot of blues and grays. And only in the last 10-15 years, have I ventured out to more fashion- able styles and colors, if you will. I think just getting more involved with dinners, charities, and entertain- ing, I wanted to broaden the selection of fashions and colors in my wardrobe. I’ve got a green-ish outfit I wear during the spring, especially on St. Patrick’s Day, and then some houndstooth sports coats.

My favorite decade of men’s fashion:

It would be the 1950s-’60s, during the Rat Pack [era] … Frank Sinatra, Dean Martin, and Sammy Davis Jr. I go to the annual Cars & Cigars Smoke Detroit charity event every year, and I wear my favorite “Rat Pack outfit” with a fedora.

Where I like to wine and dine:

Nonna Maria’s, a very quaint, small Italian restaurant in West Bloomfield. Nonna Maria’s is owned by my friend John Gallagher. His family opened it back in the mid-’70s, and he’s [since] taken over and rebranded it. It is a great place to have a drink, a fabulous place to eat and entertain or take someone out.

Where I go to enjoy the arts:

The Detroit Institute of Arts is a godsend. I know I’m preaching to the choir, but it’s such a treasured institution. I went there twice to see the Van Gogh in America exhibit, [which ended in early January]. I try to go to the DIA at least once or twice a year.

My favorite music genre is …

Probably soft rock. Being born and raised here in Detroit, I’m a diehard Bob Seger fan. Yes, I love Frank Sinatra, but near and dear to my heart is Bob Seger.

How financial advising has impacted me:

It’s humbled me, it’s energized me, and it’s created in me a new level of passion that drives me to give back way more than I’ve gotten out of it.

Learn more about Serra’s financial services at

This story is from the February 2023 issue of Hour Detroit magazine. Read more in our digital edition. Check out even more fashion tips from stylish metro Detroiters at