From Mobile to Manhattan: A Sartorial Journey

By Scott Rye

Joining Loyal American Life Insurance Co. as a clerk in 1955, the year the company was formed, 24-year-old Matt Metcalfe rose quickly through the ranks, becoming secretary and a director just three years later, and executive vice president two years after that. At the beginning of 1960, the company listed assets of $3.5 million. When American Annuity Group acquired Loyal American Life in 1995 as part of its buyout of Canadian holding company Laurentian Capital Corp., Loyal was valued at $312 million.

In the intervening years, Metcalfe proved to be a visionary leader as he took on the role of Chairman of Loyal American and, later, became CEO of Montreal-based Laurentian Capital, which owned Loyal American. Metcalfe habitually wore Brooks Brothers suits and ties, whether he was shuttling between corporate headquarters in Mobile, Alabama, and his office on Fifth Avenue, attending various board meetings in Montreal, London, or Geneva, or relaxing at the Metropolitan Club, where he served as a Governor and is now the longest-standing member.

When we sit down to talk, Metcalfe is wearing a button-down blue pinstripe shirt, a navy cashmere V-neck sweater, and chinos.

IVY STYLE:  Matt, you were named to several “Best Dressed” lists over the years. How did your sense of style develop?

MM: I was always interested in clothes, particularly shirts. Suits and trousers were all right, but for me, the shirt was the thing. I ordered my first made-to-measure shirt when I was 12.

IVY STYLE: Twelve years old?

MM: The Packard Shirt company sold made-to-measure shirts through the mail. I had my measurements taken and picked out the details for the shirt. 

IVY STYLE: What was the shirt like?

MM: Oxford cloth. Packard sent me a letter saying that they had no representatives in the Mobile area and asked if I would like to become their representative.

IVY STYLE: They had no idea you were only 12.

MM: They offered a 50 percent discount for any shirts that I purchased as their representative. (laughs) I think I sold one shirt.

IVY STYLE: Did you make any other style investments at age 12?

MM: No, but I had my eye on a watch at a jeweler’s shop on Dauphin Street. I finally saved up enough money to make a down payment on it when I was 14. I think I paid five dollars a week on it after that.

IVY STYLE: What was the watch?

MM: A Jaeger-LeCoultre. I still wear it today.

IVY STYLE: You have the same watch you bought when you were 14? For the record, how old are you now?

MM: Ninety-one.

IVY STYLE: So, you’ve worn the same watch for 74 years.

MM: It’s been back to Switzerland a couple of times for repairs.

IVY STYLE: That’s value. You started wearing Brooks Brothers early on. How did that come about?

MM: We had several board members at Loyal who were from New York. I liked the way they looked, so, I started wearing Brooks in the 50’s.  I remember walking into the store for the first time. The thing I remember most is tables and tables stacked high with trousers…

IVY STYLE: And you always wore suits?

MM: I traveled a lot, especially when we began acquiring smaller insurance companies across the country. I like to travel light, and wearing a suit is the easiest way to do that.

IVY STYLE: And you wanted to project a certain image.

MM: (shrugs to concede the point)

IVY STYLE: Who was your biggest influence?

MM: One of my earliest influences was Mr. Ben May, president of Gulf Lumber [and founder of the Ben May Institute for Cancer Research at the University of Chicago]. He had a vast fortune, and, of course, I was attracted to that. I used to see him often at his summer place on the bay. (laughs) I would stand around, hoping he would say something to me. I knew him well in later years. I worked with some great people during my career. Loyal American’s first president, Jimmy Faulkner, became a life-long friend. Mark McKee was on our board. He’d been on the Pan Am Board for years by then and was a great old gentleman, but it was Malcom McLean who had the greatest influence on me.

IVY STYLE: Malcom McLean purchased Pan Atlantic Steamship [later Sea-Land] and the Waterman Steamship companies in Mobile the same year Loyal American started. He originated the idea of containerized shipping.

MM: An innovator and true visionary.

IVY STYLE: How did you meet?

MM: In 1970, a group out of Texas was trying to buy Loyal American. They had a history of buying companies and raiding their assets. I couldn’t let that happen. I filed a complaint with the state insurance commissioner, who put them on notice, and then I got on the horn and called Mr. McLean to see if he would buy a controlling interest.

IVY STYLE: You placed a cold call to Malcom McLean?

MM: I started telling him why he should invest in the company. He stopped me and said he’d see me at 9 o’clock the following morning in his office in New York. I hopped on a plane and met him the next morning. We met for two and a half days. It was intense. Mr. McLean didn’t suffer fools. He also didn’t engage in small talk.

IVY STYLE: What was the result?

MM: He agreed to purchase 70 percent of the company. His $5 million investment grew to more than $20 million by the time he sold. I sat on several boards with him. When he spoke, he was sharing his wisdom with us younger board members. He didn’t need our advice. He was imparting his knowledge. Working with him was better than getting an MBA from Harvard.

IVY STYLE: How would you describe McLean’s sartorial style?

MM: Mr. McLean always dressed in a suit and tie. 

IVY STYLE: I’ve seen a number of photos of him wearing a fedora.

MM: He did. He often wore a hat. He famously—and I use that word intentionally—wore gold cufflinks. Most men didn’t wear French cuffs then, except with a tuxedo. The cufflinks were square, as I recall, and they must have meant something special to him because he always wore them.

IVY STYLE: Thank you, Matt.

Metcalfe retired as CEO of Laurentian Capital in 1988, then joined AFLAC as a lobbyist in D.C., working the halls of Congress and the cocktail circuit, all the while impeccably dressed in Brooks Brothers suits and ties and bespoke shirts. He also collaborated on numerous deals with Anthony “Ben” Walsh, one of author Hilary Rosenberg’s so-called “vulture investors” from New York, scooping up distressed businesses across the country. But that, as they say, is a story for another time. Most days now find Metcalfe dressed in an open collar shirt, V-neck sweater and chinos, or perhaps a tweed jacket and flannels as the weather dictates.


  1. Matt Metcalfe, wearing Brooks Brothers in 1965.
  2. Metcalfe’s Jaeger-LeCoultre watch, which he purchased in 1945.
  3. A recent photo of Metcalfe, still well-dressed in his 90s.

7 Comments on "From Mobile to Manhattan: A Sartorial Journey"

  1. Great story! Given the rate at which a twelve-year-old boy grows, I’d bet that made-to-measure shirt didn’t fit for long.

    The collar points under the lapels look great. It looks like a broadcloth button down, an excellent, all-business look.

  2. Charlottesville | December 27, 2022 at 1:17 pm |

    Thank you, Mr. Rye and Mr. Metcalfe for the very interesting interview and great pictures. A very accomplished and well-dressed man indeed.

  3. Wonderful piece! Also, a great reminder that quality overrides quantity – an especially important point in today’s temporary mindset.

  4. Debbie Amsbaugh | December 27, 2022 at 1:37 pm |

    Great piece. I was most impressed with the watch purchase. Quality and style are timeless. I feel that this piece highlighted that.

  5. I want/hope to look that good when I grow up!

    Seasons Greetings,


  6. A man with style and class – more than comes through in Mr Rye’s writing.

  7. Poison Ivy Leaguer | December 29, 2022 at 7:15 pm |

    The Packard Shirt Company, Wow that’s a blast from the past! In about 1966-67 one of my fraternity brothers was a Packard rep. They had a tremendous assortment of fabrics, collars, cuffs, fullness options and pleat options. Since they were made to measure, size was never a problem. The quality was good, and the price was approximately equivalent to Arrow. Monograms were available for about a dollar. One of the guys, whose initials were W A S, was wearing a Packard with a W R S monogram. I asked, “What happened< Waly? Did Dave screw up your order?" "No" he replied, "I just thought a shirt that says WAS would look stupid." OK, Walt whatever. Thanks for a fun memory.

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