Dressed for success
It’s tricky interviewing people for jobs these days, just as it’s tricky being interviewed. In an age where moving up too often means moving companies, it can be tough for Boomers to understand the continuity behind a resume that shows eight jobs in ten years, or a series of very different roles as if the applicant is looking for the right peg to fight the right hole.
The critical differentiator is being able to tell a convincing story about your career journey. So long as you’re able to explain the decisions and trajectory, you should be in good shape (should be—lots of oldies still can’t work out why you’re not with a company for life, as if companies still view employees that way anyway). Here’s my problem: I’m coming to realize my narrative is actually less around a logical career trajectory than it is about fashion.
Bear with me here. Living in the Brisbane suburbs in the late 1980s, fashion began to seep into my consciousness. Country Road Australia was everywhere in my senior year—how I wish I still had those catalogs, all desert boots and shorts and the company’s legendary chambray shirt—and there was really only one choice when I needed dressier clothes for my first job (in the toy department at David Jones in the Queen Street Mall, just before Christmas 1989). I went to Country Road with my parents and emerged with a pair of bang-on tan chinos, but they drew a smidge of ridicule from my manager when she wondered aloud how low the crutch was.
Still, I was evolving. My job at David Jones lasted only two weeks as I was hired by The Courier Mail newspaper, and that required fashion on a new plane (not that anyone in the newsroom would have really cared). There were several months of conversations with colleagues about getting my first real suit, and for that there was also only one choice: hitting Brisbane’s Mitchell Ogilvie for a double-breasted Zegna Soft number, following hard on the fashion heels of then Prime Minister Paul Keating. Man, I loved that suit. Soft shoulders, great texture, able to be worn as separates … legendary. It was also, for me at the time, quite the investment—but on a cost per wear basis, I got my money’s worth.
On the side, I was hitting David Jones as a customer for the latest casual gear from Polo Ralph Lauren, notably a fantastic navy and white striped rugby top with a red Polo logo, which I even continued wearing after a big mud stain defaced half of the back. I guess it was an early effort at wabi-sabi. And I was devouring issues of American GQ edited by the legendary Art Cooper. I accumulated years of them, which took pride of place on my black leaning Allen-key-assembled apartment shelves. GQ transformed my sense of what it meant to be a man, and the liberal smattering of astonishing women didn’t hurt either (Exhibit 1: the Heidi “Boom-Boom” Klum cover in January 1999). My memory of those issues throughout the 1990s is so vivid I can remember their distinct smell from all the fragrance ads with sample strips.
When I turned 21 and went backpacking, my priorities were a little different. I wore a heather gray cashmere crewneck sweater with shorts in Manhattan and heard a lady loudly snort “shorts with a sweater?” as I passed. As it happened, I was walking from the youth hostel to see Ralph Lauren’s Rhinelander mansion flagship store on the corner of Madison and 72nd. And no one at the store batted an eyelid. My big scoop from the city was a Barneys balmacaan (it was in my closet for 25 years), which joined a ridiculously oversized linen button-down I’d picked up at Banana Republic in San Francisco.
A couple of weeks later, I won about 400 Deutsche marks at a Berlin casino and promptly hit the Zegna store and bought a pair of pants. As I said, I wasn’t a typical backpacker but, in my defense, I wore those pants 17 years later in Venice and felt pretty darn good. Then, after spending my entire six months of travel scouring the globe for a pair of specific Polo Ralph Lauren tweed pants, I wound up buying them where I’d first seen them: at the very same David Jones store where I was briefly a toy salesman.
So, fashion and I go way back. But here’s my slightly weird realization. Lots of people buy some clothes when they get a new job—that’s pretty standard. But I tend to factor in what the fashion options are before I take a new job. And the idea that I can look a certain way has definitely tilted a few decisions.
I mean, I went a little nuts at John Varvatos’ SoHo store (relatively speaking—it was modest but felt like a lot to me) when was largely unsuccessfully freelancing in the mid-aughts. The fact I had a crush on one of the salespeople (Ashley, and I never summoned the nerve to ask her out) played into that, but I was definitely attempting a cool-dude-freelance-writer vibe. I mean, a denim jacket with chocolate velvet lining? Come on!
After joining McKinsey in 2007, Dunhill got a workout. Beautiful suits, to match the crazy-expensive dopp kit I’d picked up at its Sydney store back in 1997 or so. When I left McKinsey for roles requiring regular international travel, thoughts immediately turned to potential in-flight options: Boglioli drawstring pants, Common Projects sneakers, James Perse tees, Rimowa carry-on. And the chance to leave the corporate world behind for a much smaller company appealed because it pushed me deep into the elevated casual zone.
Is this a terrible north star for a career? Maybe. But things have worked out OK, and I’m thinking picking jobs based on what you get to wear isn’t necessarily the worst strategy. After a slightly meandering path often filled with learning what I don’t want to wear, I’ve ended up able to dress in a way that’s the truest reflection of who I am. It’s surely no coincidence that aligns with the role I now have at the company I work for. Now, if I could only find a treasure trove of 1990s Country Road and Ermenegildo Zegna catalogs …