This week, we visit with Leo and his partner Jordan in a typical day at their law practice.
I was in the office last Friday putting the final touches on a complaint for a law suit we were filing the next week. I was so engrossed in my work that I didn’t hear Jordan walk into the office from court.
“Hey, loser.” His standard greeting.
I looked up, and what I saw made me topple over in my office chair from fright.
Now normally, I’m not terribly afraid of Jordan. I am sure he could take me in a fight, but he’s got sort of this angry teddy-bear aura around him. No, it wasn’t Jordan himself that spooked me. It was his outfit. I was gobsmacked.
Picking myself up of the ground, and brushing myself off, I indignantly demanded “what the hell are you wearing? You call yourself a lawyer? You don’t look like any professional that I’d ever hire. In fact, you look like a slob.”
Jordan pouted for a moment, then rebounded. “Well, you look like a loser.”
I sighed. “Haven’t you ever heard the term ‘dress for success?’ You’re dressed like a used car salesman, not a lawyer.”
“I do excellent legal work. I don’t care how I look.”
“Well, I do, and your clients probably do too. Seriously, do me a favor—take the few minutes that you’re going to waste tweeting at your internet lawyer friends Brian Tannebaum and Scott Greenfield this morning to acquaint yourself with my friend, Mr. Iron. And are those … are those coffee stains on your shirt?”
“Maybe. I don’t know. Could also be wing sauce”.
“Well get a Tide pen. And that suit — is it black? Are we the Undertaker Law Group, now?”
Jordan shooed me off with a dismissive wave as I followed him into his office. But I had just laid my talons into him and wouldn’t be deterred by a simple hand gesture.
“And your tie? Listen, I know Jerry Garcia was a great jam band frontman and all, but he’s a much better musician than a tie designer. Also, he did a lot of drugs, and his tie designs don’t lend themselves well to a professional image. You should have ceremonially burned it with some incense at his memorial.”
“I should have ceremonially burned you at the stake,” he retorted, as he took off his backpack and sat behind his desk. I cringed.
“Finally … are you wearing a backpack … with a suit?”
Crestfallen, I shook my head in silent defeat and retreated back to my office. I was shaken — unable to focus on my complaint — and wondering how my partner had been led so far astray.
So instead of wasting my time silently mourning the loss of men’s sense of proper professional dress, I channelled my energy and put pen to paper. Or fingertips to keyboard.
Your Image Matters
If you’re anything like most professionals out there, you might not give a second thought to how you dress in the morning. You may approach it as a simple checklist —
- Shirt? Check.
- Suit? Check.
- Tie? Check.
- Shoes? Check.
- Underwear? Check.
— without giving a second thought to the overall ensemble and image you’re projecting.
Well, listen, pal, you’ve got a lot of learning to do. So while you’re wasting your billable hours reading this article, you might as well learn something useful about professional men’s dress.
“Professional Men’s Dress”? What the Hell Does that Mean?
We work in one of the few professions where wearing a suit is still mandatory for most. The suit is a sign to others that “Why yes, I am a lawyer”. Now that dressing for dinner and black tie parties are largely a vestige of the past, the suit represents the realistic pinnacle of formality in today’s increasingly informal world.
My aim in this series is to provide you with the building blocks for a professional wardrobe. Granted, if you follow my tips, you’re not going to demand attention like Gordon Gekko at a shareholder’s meeting, but you’ll be able to assemble a reasonably conservative, professional wardrobe without having to give it too much thought.
“Suit” — the term itself can be used as a pejorative, named for the authority figures who wear them.
Though if you take a minute to think about it, there are a few reasons that we’re expected to dress professionally. Many clients know lawyers only from TV and Movies. And with the notable exception of My Cousin Vinny, most of the time lawyers are portrayed in film, they’re wearing suits. Despite the sweltering Alabama heat, did Atticus Finch wimp out and wear a polo shirt and jeans while defending Tom Robinson? Or how about Jack McCoy—you ever see him prosecuting bad guys in a t-shirt and cargo shorts? You have expectations to live up to!
There’s a more important reason for this expectation too: we’re fiduciaries who are trusted to zealously advocate for our clients and represent their best interests. Not only is this a huge responsibility, it’s a high honor.
Is a suit going to turn you into the next Clarence Darrow? Probably not. But shouldn’t your appearance reflect the respect that this responsibility is due?
I suppose a proper introduction is in order, so today I’m going to tell the story of how I grew to give a damn about how I look.
There’s a Method to My Madness. Also, I Used to Wear Really Ugly Stuff.
I wasn’t always this way. I didn’t alway care about the way I looked. Well, to put it another way – I did, though this was in middle school during the 90s, when ironic product t-shirts, JNCOs, and intentionally ugly and garish button-up shirts filled my wardrobe. Look here:
Yes, this is me. I was featured as #15 on Buzzfeed’s 18 Things You Wish You Could Forget About Middle School. Sometimes, I still miss this shirt.
But I eventually grew up (sort of) and decided that the time had come for me to start dressing like a grown up. This happened sometime in my early 20s, when I bought my first “real” suit—a navy, 3 button, Hugo BOSS suit I purchased from our local retailer. I felt like a million bucks wearing that suit, and thus began my foray into professional menswear.
Like many who find a new hobby, I dove right in, scouring the racks at my local menswear stores for the sharpest clothes I could find. And like many new devotee to anything, I suffered from a certain degree of hubris when it came to my appearance and talent for dressing. Armed with my GQ and Esquire, I started building up an arsenal of suits, shirts, ties, and shoes.
When I started representing clients in court during my 3rd year of law school I donned slim-cut, fashion forward suits. Hell, I even entered a contest for a walk-on role on Mad Men. I amassed a collection of 60s era vintage slim ties. My shirts were slim and cut slightly shorter than traditional. The shoes? Ugly beyond words, and mostly unsuitable for court. My rule with socks was “the brighter the better”. While in school, I wrote an insufferable blog about menswear, much to the chagrin (amusement?) of my classmates.
Yup, that’s me in 2007. With a red shirt. And that navy Hugo Boss suit. And an ugly paisley tie. And Joshua Chamberlain facial hair.
But let’s take a moment to ponder this photo. You might now be asking yourself, “why the hell did the Lawyerist let this guy anywhere near a style column”? I wasn’t all bad back then – I had my good days too. Here’s a picture of me singing Karaoke. To Vanilla Ice’s Ice, Ice, Baby.
Not too shabby for karaoke, eh?
The Turning Point – Whereupon my Face Matches the Color of my Socks.
Since my red-shirted Chamberlain-facial-hair era, I’ve realized the error of my ways and repented for my sartorial sins. Today, as I think back upon what I was wore to court back then – only two years ago now – I can only shudder.
I can remember one day in particular that really began to define my new approach. I was at police district for preliminary hearings, and thought myself dressed to kill: a grey glen-plaid suit, black tie, black shoes. And Bright. Pink. Socks. With Navy Polka dots. Standard go-to-hell socks with an otherwise sedate outfit. And I was champing at the bit to try my case.
After sitting for a few hours waiting for my case to be called, the judge looks up and calls out: “Hey, socks, looks like you’re up”.
I’m pretty sure my face matched after the judge called me out like that. I consider that my low point.
When I got out of court, I thought a long while about both my wardrobe and my judgment. Shortly thereafter, I committed myself to a relentless dedication to dress as professionally soporific as possible – that is, within the boundaries of classical men’s dress enough that I always look put together, but never so ostentatious that I find myself called out by a judge. Never again.
So where does that put me in the scope of this column?
I’m striving to help you learn the most essential, basic elements toward building a professional wardrobe. My goal is to give you the guidelines so simply that you can blindfold yourself, pick out a suit, shirt, and tie, throw them on, and still look great.
What About My Personal style?
To give you a hint about how I’m going to approach this ongoing series, I guess I’d be helpful to gauge my own approach to style. I like to think of myself as a mid-century classicist. Some on the internet might call my personal style “trad”, “ivy”, or even “preppy”. You can call me whatever you want. (Yes even that. I’ve heard worse, I’m sure, from my law partner). If you care to follow me on instagram, you can see some occasional self-indulgent and narcissistic shots of my shirt/tie/coat combinations via my handle @ivy_thrasher. (There are also many dog pics, as I have three. Deal with it).
What Do I Hate?
I hate black suits and notched lapel tuxedos. Square toed shoes and corrected grain leathers make me upset. If your shirt is darker than your suit, you’re doing it wrong (court isn’t a nightclub). Lapel pins of US flags are pandering and silly. Wearing “athletic” or “slim cut” suits is overrated. If your double breasted suit is from between 1980 and 1995, and you’re not Patrick Bateman, you should stop wearing it.
It Seems Like I Hate a Lot of Things. What Do I Like?
I profess a love of sack-suits and longwings. My shirts are generally a boring blue or white (or a combination of the two). My ties are generally sedate, though I might throw in a bow-tie now and again. Sometimes, I look like a Kennedy-Johnson-Nixon era mid-level bureaucrat (read: Don Draper, but far less attractive and stylish).
In case you haven’t learned by now, I’m opinionated and occasionally insufferable.
What’s My Angle?
Understand that my tastes trend toward the boring and traditional, and my goal is to provide the sartorial equivalent of teaching you how to fish. Whatever reels or bait you prefer after I’ve laid out the fundamentals is wholly up to you.
I’d also enjoy taking whatever questions you might have to ask in a future Q&A column. Note, however, that I reserve the right to answer with snark (It’s the lingua franca at my firm). By reading this column, you waive the right to be upset by my posts or answers.
In my next post, I’ll address the two species of the “that guy” genus – Thatguyus Schlubbius and Thatguyus Dandius – and how you can avoid the trappings of either. In the meantime, send your questions, suggestions for future topics, and hatemail to Leo@Lawyerist.com.
Until next time, govern yourselves accordingly.
(photo: Sleazy car salesman image from Shutterstock)
Read the next post in this series: "Men’s Suit Colors for the Clueless."