Dressing the Part of a Young Lawyer

By Evan Loeffler


When I first entered the legal workforce as an associate, my boss’s wife made it a mission to do something about my persistent bachelorhood. To this end, she set me up on several dates. In evaluating these dates, it is interesting to note two facts: first, they were short-lived, rarely lasting as long as three hours; and second, they were all with different people.

To Penny’s credit, she was persistent. After some time, however, she changed her strategy. She walked into my office one afternoon, and dispensing with all chit-chat, made a statement that struck fear and trepidation into my heart:

“I’m going to help you pick out a new wardrobe.”

I am one of first to admit that I am not a spiffy dresser. I do own suits, and am known to wear them when the occasion requires. I am happy, however, to wear khaki trousers and a sports jacket. This, I reasoned, was more cost-effective, since I would not have to pay for professional dry cleaning.

“What’s wrong with what I’m wearing?” I asked, trying not to sound defensive.

“When was the last time you ironed that shirt?” she asked.

“What are talking about? This isn’t a golf shirt.”

“Not that kind of iron! A clothes iron.”

“The label says ‘permanent press.’”

Penny shook her head incredulously and changed the subject.

“Bow ties are out, Evan.”

“Straight ties make me look short,” I explained.

“You are short! Look, for four or five thousand dollars, we can get you a new wardrobe and you’ll look great.”

“Thousand’?” I echoed. I did not feel that complaining to my boss’s wife about my salary would be fruitful. “How much better can you make me look for fifty bucks?”

“Look, Evan, I’ve already discussed this with my husband, and he agrees you need to dress better. You want to make a good impression on people professionally as well as socially, and you’re not helping yourself by looking like an extra from Invasion of the Unmade Bed People. You should dress up when you take people out.”

“Penny,” I said, “I don’t need to dress up just to take my date to McDonald’s.”

“You’ve been taking your dates to McDonald’s because no decent restaurant would let you in the way you dress.”

This was true. It is amazing how often upscale restaurants lose reservations. I played my ace. I figured if I could whether the storm she would forget the whole thing in a day or two. “Fine,” I said. “Let me check my calendar to see when I have time to go shopping with you.”

“I already got you the rest of the day off,” she said. “Let’s go.”

In addition to my general indifference to expensive clothing, I hate shopping. An afternoon spent shouldering my way through crowds of shoppers for the privilege of spending money I don’t have on stuff I don’t want is not how I like to spend my leisure time. Given the choice of going clothes shopping and being bitten in half by a shark, I’d have to think about it.

Penny took to me to a men’s clothing store where she announced that she would be doing all the talking and that I would buy what she recommended. She then collared a salesman and, indicating me, stated that her husband needed a new suit. Both the salesman and I were shocked.

“A new suit?” I said.

“Your husband?” said the salesman, looking me over.

“That’s right,” said Penny. What’s your suit size, honey?”

I stated I had no idea since all my suits were hand-me-downs from my father. The salesman whipped out a tape measure and, with it, started prodding me. Eventually he came back with a garment whose most distinguishing feature was the length of its price tag. At Penny’s insistence I tried it on and happily pointed out that it did not fit correctly.

“The pants don’t fit,” I stated, gesticulating at the trousers whose legs trailed two feet behind me.

“We can fix that, sir,” said the salesman as he started drawing on me a piece of chalk.

“Don’t you have anything here that fits me out of the box?” I asked indignantly. “What sort of store is this?”

The salesman looked over at Penny for help. Penny commanded me back into silence, where I remained while the salesman nipped and tucked at me. In the meantime, Penny and another salesperson put together a collection of matching shirts, ties, socks and other suit paraphernalia. My car keys were then held for ransom until I purchased the whole ensemble.

A few days later, I arrived in the office wearing my new suit. The other lawyers took note and commented on what a fine figure I cut in a suit that fit correctly. My boss then called me into his office where he began by agreeing that the suit was a step in the right direction.

“The reason I wanted to speak to you, though, is about something different. I ran into my tailor yesterday and he said how sorry he was to learn that Penny and I were no longer married. I told him we were still married and demanded to know what the hell he was talking about. He said my wife was in the store a few days earlier with a short, unkempt individual buying a suit. She kept on referring to this individual as her husband. Do you know anything about this?”

“Ummm. Nope.”

“Hmmm. Strange,” he pondered. “Well, let me know if you learn anything.”

Despite his ongoing inquiries, my boss was never able to learn anything further about the mysterious individual seen with his wife. My desire to not appear as a “short, unkempt individual” increased markedly. I learned to iron my own shirts, scrapped my collection of clip-on ties, and found a dry-cleaner. To this day, however, I have not found anything to help me look less short. Elevator shoes do not come in wingtips, and stilts would clash with the suit unless they were painted basic black. Any suggestions would be greatly appreciated.

Evan Loeffler, is now of counsel with the law firm of Harrison, Benis & Spence, LLP, in Seattle, Washington, where Penny’s husband is still a partner and will remain nameless for the sake of continued office harmony.

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