08/06/2012 09:09 am ET Updated Oct 11, 2012

My Blouse Almost Got Me Thrown Out Of Prison (And Other Adventures In Lawyer Style)

A few years ago, a friend circulated a picture taken during our first year of law school. We all looked young, bright-eyed and optimistic. However, rather than revel in our collective youthful glow, I could only fixate on one thing: The headband I was wearing.

This being the late '90s, there were other alarming elements of my ensemble -- dark lipstick that was ill-suited to my skin tone, a corduroy mini-skirt, clogs (clogs!) -- but I kept returning to the headband. More troubling was my realization that, if this younger version of myself could not reach the obvious conclusion that a headband should never, ever sit atop my large noggin, where else had I gone wrong? This person had been running around (in clogs, no less) making crucial life decisions: choosing classes, accepting or declining dates and applying for potential jobs. How could anyone trust a girl who could make such a simple, but crucial, sartorial error?

My first job out of law school was at a big, well-respected, vaguely scary law firm. The law firm represented important clients in matters that, as they liked to say, appeared on the front page of the Wall Street Journal. People went into the office in the morning and did not emerge until the wee hours of the following morning, if at all.

Perhaps perplexed as to why this venerable institution had selected me to join its ranks in the first place, my strategy when it came to attire was to try to blend in. To at least look purposeful, smart and competent, until I became these things. In order to accomplish this, I marched into Brooks Brothers and Ann Taylor, expecting to be issued an inoffensive uniform suitable for a serious officer of the law.

Sure, I chose a few colors (navy, tan, brown), but I did not think outside the box. As a result, I looked like a box (on good days, a rectangle). Most of my suits were, well, boxy. Even my low-heels were vaguely square. Under these suits I wore either shapeless button downs or sleeveless tops with high necklines.

After a few years of practicing law, I moved to a smaller firm that frequently represented clients facing criminal charges. The stakes felt even higher and I was often just as busy as I had been in my first job. The demanding job prevented me from "blossoming" personally, so I hoped the professional clothes I wore everyday could do so for me.

I would make quick jaunts to the overpriced boutique around the corner to experience the collective fawning of the sales staff when I would trot out of the dressing room in a suit with a belted red jacket and fishtail skirt. When things got busier and I got out less and less, the suits got more aggressive, until one day when I found myself walking into my office wearing a powder blue plaid pant suit. Stylish? Yes. Appropriate for an officer of the law? Debatable.

One day during this "stylish" phase, I had to go to federal prison to participate in a meeting between my client and a probation officer. This was not my first trip to prison to visit a client. The senior associate supervising me asked me to "Please just wear something conservative - like trousers." I dutifully wore one of my "trouser" suits nonetheless (looking much like a pre-Secretary of State Hillary Clinton). The dress code posted at the prison security desk specifically prohibited "see-through tops" and "backless shirts." The messages from both the prison (this was a serious place) and my colleague (we are serious professionals) were clear: Do not cause a riot.

After many riot-free visits to incarcerated clients, I felt fairly secure in my selection of a drab brown pantsuit on that fateful day of the probation meeting. As was my wont at the time, I included a subtle nod to my recent clothing renaissance -- a silky brown top that buttoned above my cleavage, but also had a tie at the neckline. In retrospect, not the best look, but I did not think a controversial one.

When I arrived at the prison, I checked in downstairs and uneventfully passed through security under the watchful eyes of several guards. I was next escorted to the elevator to go to the visiting room. The female guard escorting me leaned back against the elevator wall, raised her eyebrows and looked me up and down with a mysterious look that could've conveyed anything from indigestion to revulsion. Without taking her side-eyed glare off me, she pulled her radio in front of her mouth and mumbled something. I mentally reviewed my outfit to figure out what could be causing such obvious offense.

When I arrived at the visiting rooms, it quickly became apparent that the guard giving me the stink eye had alerted the guard in the visiting room to my presence. This guard immediately and loudly declared that I had to leave due to my inappropriate shirt. In that instant, I was whisked from the ranks of respected officers of the law and into those of the tube-topped titilators the state prison dress code had warned me about all those years ago.

However, even if I was standing before someone who viewed me only as a two-bit hussy, I knew that I was also a lawyer who had to see my client. I proceeded to try to explain the nuances of my blouse in a low voice. To the extent there was a peek-a-boo effect, it was only with regard to skin that would have been revealed by one of my Brooks Brothers button downs from my early days.

As is probably the case any time one finds oneself arguing that they are not, in fact, dressed like a floozy, it was a tricky situation. The guard's obvious disdain caused her eyes to roll in a manner that suggested an impending seizure. Ultimately, I proved that I had developed some lawyerly skills as I negotiated my way into the meeting.

The prison run-in taught me that nothing -- neither my desire to "blossom," nor any amount of cooing from saleswomen --could overshadow the fact that I was in a serious profession with little room for sartorial risks.

Here, the characters whose sartorial skills in the courtroom have entertained us for years.

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