A guy walks into a conference room:

He’s wearing a custom-tailored suit and a shirt with monogrammed cuffs. His pocket square matches his silk tie. His cufflinks are diamond-studded, and the watch is a Rolex. How do you react?

Choice one: “My goodness, this fellow is stylish and obviously rich. He must be a great lawyer.”

Choice two: “All hat; no cowboy. If this clown were any good, he wouldn’t have to worry so much about appearances. Who does this fop think he’s fooling?”

I know that the conventional wisdom instructs people to dress for success; I’m only partly convinced . . .

When I was in private practice, I had a New York-based partner who was notorious for dressing like a slob. He looked as though he intentionally wrinkled shirts before he put them on in the morning. He didn’t bother with that “tucking in your shirttails” thing. Weeks-old coffee stains didn’t bother him a whit.

We were representing a U.K.-based bank in a massive securities litigation. The two in-house lawyers who had flown in from London were classic Brits, dressed to a tee. During a break, my partner left the conference room, perhaps to pour more coffee on his shirt. The junior of the two in-house lawyers turned to his colleague: “We’re not actually going to let this fellow represent us in court, are we?”

The senior guy looked back: “This man is a senior partner at a leading international law firm. And do you see how he dresses? Do you know how good he must be to get away with that? Of course we’re using him.”

Dressing well can cut both ways.

I’ve already staked out my public stance on the “dress for success” issue. Chapter Eight of The Curmudgeon’s Guide to Practicing Law — “Dress for Success” — reads, in its entirety:

“I don’t give a damn what you wear.

Just make sure the brief is good.”

Before the book went to press (in 2006), both of my editors at ABA Publishing told me to revise that chapter: Start with those two sentences, but then go on to explain that lawyers can’t wear torn jeans to the office. Or leave those two sentences as the text of the chapter, but then drop a footnote explaining that the text overstates its point.

Torn with conflict, I naturally asked the hero of my Inside Straight columns — my 15-year-old son, Jeremy — for advice: “You could change it, Dad. But then it wouldn’t be funny anymore.”

I thought Jeremy was far more convincing than the two professional editors, so I left the chapter on fashion as it was. And two things happened: First, many reviewers of the book quoted that chapter (in its entirety) in book reviews. This outraged Jeremy: “Dad, they’re stealing your joke. Now no one will buy the book.” But this suggested that at least a few people thought the idea was funny.

Second, several reviewers (and other readers who sent me personal notes) took issue with that chapter of the book alone. From one of my female partners: “Mark, you were probably just kidding, but that’s really bad advice. Women, in particular, can’t wear provocative clothes to work or drench themselves in perfume; that can kill a legal career.” Or, from a well-respected senior partner at a Philadelphia-based firm: “The only advice that is flatly wrong is the chapter on dressing for success. I’ve actually gone out for a stroll at lunchtime, run into an acquaintance, and been retained before I returned to my office. That would never have happened if I hadn’t always dressed professionally.”

In my heart, I’ve always been a substance over style kind of guy. But I concede that my critics are not entirely wrong.

When you’re starting your career, be careful about letting your dress become a distraction. As you become better established, you’re likely to have more flexibility.

But no matter how you dress, I’m sure I was right about one thing: “Just make sure the brief is good.”


Mark Herrmann is the Chief Counsel – Litigation and Global Chief Compliance Officer at Aon, the world’s leading provider of risk management services, insurance and reinsurance brokerage, and human capital and management consulting. He is the author of The Curmudgeon’s Guide to Practicing Law (affiliate link) and Inside Straight: Advice About Lawyering, In-House And Out, That Only The Internet Could Provide. You can reach him by email at inhouse@abovethelaw.com.


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