Watching the sixth season of the West Wing on DVD last week, I was struck by a scene in which White House Deputy Chief of Staff Josh Lyman heads over to the office of Republican Senator Arnold Vinick, to find the Senator enrapt in shining his shoes.

“Mr. Chairman.”
“Shine your own shoes, Josh?”
“No. I can’t say that I do.”
“My father used to say, you can’t trust a man who doesn’t shine his own shoes.” Looks down at Josh’s feet “Does anyone shine those things?”
“Not really. No.”

At this bit of dialogue, I flashed on my own shoe rack – brown boots and black oxfords slowly descending towards the same scuffed blur of grey. And I thought, perhaps it’s time to start shining.

So, earlier this afternoon, I picked up a brush and a stack of polishes at the local Duane Reade. And, in between chipping away at the huge stack of emails in my inbox (Oh in Ohio, T-minus five days), I set about shining my shoes.

Thus far, I’m hugely pleased, both by the finished shoes – which look surprisingly good considering my rookie shiner status – and by how I feel. Perhaps it’s just the inhaled polish fumes talking, but, in a line of work that seems always a nebulous, swirling mess, there’s something remarkably gratifying about getting something finite, real, noticeable and concrete accomplished, just within the space of a single afternoon.

Do any of you guy readers wear tank-top undershirts? And, if so, can you explain what the hell that’s about?

So far as I’ve always understood them, undershirts are meant to keep you from sweating through into the outer shirt. But I – and I think I’m not the only one on this – mainly sweat from the armpits; that’s why we put deodorant there.

So, if a tank undershirt specifically doesn’t cover your armpits, than what, exactly, is the point?

For the past four or five years, I haven’t bought a pair of jeans. Instead, I’ve shopped in my younger brother’s closet. Unable to resist buying new pairs, my brother David has happily passed along his ‘hand-me-ups’ as they’ve been displaced by newer editions.

The problem: my brother’s waist is about an inch and half larger than mine. And while I’ve taken to simply cinching down the excess with belts, a slew of female friends have recently pointed out that, in short, it looks retarded.

So, I set out to buy a pair or two of new jeans. And, in the process, I discovered I’m no longer really a 30-30, and closer to a 29-30 instead.

After extensive searching, I made a second discovery: while 30-30 jeans are easy to find, 29-30’s don’t seem to exist. Drop to a 29 inch waist and everything comes solely in 32 inch length. So, realizing I’d already spent embarrassingly long on the jean search, I quit while I was ahead and picked up two 29-32 boot cut pairs from Banana Republic.

Which sent me, after washing each pair twice to counter initial shrinkage, off to have the jeans tailored.

Previously, I’d simply taken any about-right length as good enough. Now, faced with the chance to trim to perfect size, I could angst about a whole brave new world of jean fitting concerns.

Shorten them to fit with a pair of oxfords, and a set of flat-bottomed sneakers drags the back of the jeans an inch and a half underfoot with each step. Flip things around to fit the sneakers, and the jeans look like high-waters with anything else.

So, after a week or two of serious consideration, I simply gave up, had them tailored at some arbitrary length mid-way between the sneaker and soled-shoe ideal, and set about re-convincing myself that the whole thing isn’t even vaguely important in the broader scheme of my life

For borderline obsessives, too much choice is a dangerous thing.

After shaving off my beard for the Homecoming ’96 photos, I went for about a week clean-shaven. During that week, I was carded more than I had been over the rest of the last two years. Which, together with interested looks from middle school girls, convinced me that, in an effort to look old and wise and vaguely capable of running a company, perhaps it was time to regrow.

So, last Sunday, I put away the razor and let my facial follicles follow their course. As I hadn’t grown a beard in from scratch for quite some time, I was surprised to rediscover that – likely due to my fast metabolism – I can go from zero to past seriously scruffy in well under a week. Normally, at the one week point, I’ll then start whipping out the beard trimmer every few days, evening things out and keeping purposefully at the at-least-sort-of-indie-hip short length. This time through, however, my beard trimmer is boxed away amidst plates and CDs and spring sweaters, stored somewhere out in the far reaches of Brooklyn by the crazy Israeli moving company that won’t be delivering my things back to me until I move into the new apartment on the fifteenth.

Which, basically, leaves me with two solid weeks of unchecked growing ahead. By which point, I’m fairly certain, I’ll have passed well past ‘scruffy’, through ‘full’, and into the early reaches of ‘polar expedition’. Santa Claus, look out.

Over my pre-film years of running companies, I managed to accumulate thousands of dollars of dress clothing, most of which now hangs full-time in the back reaches of my closet. Every so often, however, I have occasion to whip some of it back out, to don suit, tie and cufflinks for a serious meeting or three.

Usually, it’s for meetings with corporate lawyers or investment bankers – people who don’t trust a CEO without a power tie. But, while I suit up intending to have the world view me differently, I find it leaves me viewing the rest of the world slightly differently as well. In pinstripes, I can spout legalese, discuss exit strategies and negotiate sticky deal points. But I can’t, for the life of me, brainstorm new, exciting, outside-the-box ideas. The tie around my neck, it seems, strangles blood-flow to the right half of my brain, letting the left take over completely.

Judging by the attire at companies I admire most, I don’t think my be-suited experiences are unusual. All the world-changing, gee-why-didn’t-I-think-of-that? ideas of the last decade or two have all sprung from a jeans-wearing crowd. Even at stodgier companies with standing dress-to-the-nines policies, the real thinking happens once people toss of their jackets, roll up their sleeves, loosen their ties, and get down to work.

I know that runs counter to today’s trend, where companies that once went ‘business casual’ during the go-go nineties are ramping back up to stricter dress codes. But I can’t help think those companies are making a mistake. Sure, take the foosball table out of the conference room. Confiscate the Nerf toys. And, for god’s sake, repaint the pipes to normal, non-primary colors. But don’t make people get dressed up. Or, maybe, do. It leaves all the more room for those corduroys-clad innovators to start taking over the world once again.

Combining my penchant for bucking tradition, and my closet full of excellent, rarely worn suits (a vestige of my finance days), I’ve officially decided to implement ‘anti-casual Friday’, in which I’ll be donning suit and tie weekly, for no reason other than that I can.

Though, also, because it looks damn good.

Yesterday evening, with my brother in town for one final night, I signed us both up last-minute for a wine tasting class at the Institute of Culinary Education. Getting ready to head out the door to the class, I grabbed my trusty beard trimmer from the bathroom cabinet for a bi-weekly touch up. Passing the trimmer over my chin, I seemed to be shearing off more than usual. “Odd,” I thought. “Perhaps my beard grows faster in the spring.” Looking at the trimmer more closely, however, I realized the longer cuttings weren’t a result of speedy growth; instead, the trimmer was apparently set at the very closest setting.

“Oh,” said my brother from the other room at the sound of the trimmer. “I was playing with that this morning. You might want to adjust it back to the normal setting before you use it.” A little late for that. I now had a mangy looking beardless patch below the left side of my mouth.

“It probably isn’t even noticeable,” my brother said from down the hallway, before turning into the bathroom, getting a closer look, and dissolving into hysterical laughter on the floor. Apparently 95% of a beard doesn’t quite cut it. So, already slightly late to leave for the wine tasting, I quickly checked the trimmer was still on setting one (a.k.a. ‘fragrance model perpetual five-o’clock shadow’), and sheared away.

As a result, I’m back to beardless. Or, at least, nearly so. And while I’m almost certainly growing it back, I can’t say I entirely minded the chance to compare, in close succession, the bearded versus unbearded versions of my face. Change can be good. Albeit, occasionally, rather unexpected.

While up at the Toronto Film Festival, due to popular demand, I decided to regrow my beard. And, for the first week or two, it looked great. Then, increasingly, people began to mistake me for a member of a lost polar expedition. It was at that point I remembered exactly why I had previously purchased a beard trimmer.

So, diving through the depths of my medicine cabinet, I brought forth the trusty Remington Precision MB-30. Clicking the dial to #5 (the setting I had always used), I shore away.

Sure, it looked immensely better than it had moments before. But the next morning, while brushing my teeth in front of the mirror, it occurred to me that I could perhaps even trim down more closely, for a scruffily indie hip sort of look. Whipping out the Remington again, I clicked to setting four and buzzed.

The results were an immense improvement, and, emboldened by that success, I began to contemplate going all the way to setting three.

Of course, beard trimming is a dicey business. Just one perilous step too far and you take on the perpetually five o’clock shadowed look so favored by fragrance and hair product models. So it was with great trepidation that I clicked that one further setting, and took a first trimming pass.

I am exceedingly relieved to say that setting three turned out to be at least as good as setting four, and possibly even better. The resulting look says, without a doubt, “I am an effortlessly cool indie hipster.” Or, more accurately “I am as much of an effortlessly cool indie hipster as I can be, considering I don’t live in Williamsburg, don’t own a trucker hat, and am actually still pretty much just a neurotic little quasi-yuppie Ivy League tech dork.”

Still, I’ll take what I can get.