Solving the Millennial Work Shirt Problem

TL;DR — If you’re a millennial who is unsure what they should wear to work, you should try wearing a banded collar shirt. Below is an explanation (perhaps an over-analyzed explanation) of why.

This Seems Like a Lot of Thought To Put Into A Shirt

I’m not naturally someone who thinks a lot about the clothing I wear. I have clothes that I have worn since middle school and repaired multiple times, and I don’t match my socks because it is the most time consuming part of doing laundry and provides very little benefit. Outside of a particular pair of overalls and a particular jacket I love, I generally have treated most of my clothing as interchangeable. Last year something happened that changed this.

Which is why I’m writing a 1000 word thought piece on a shirt.

(The shirt that launched a thousand words)
I noticed that I wore a specific shirt as often as I could and I wanted to buy more of them. It was a chambray banded collar shirt (also known as a mandarin collar or a Nehru collar) that I don’t even remember buying.

I went to go buy more of them and the company that produced it no longer made the same shirt so I bought some comparable shirts from different brands and whether fit or fabric, they invariably sucked in some way. I went to the point of buying fabric and having my friend who’s a costume designer take it apart to make more.

But this sparked the question: why did I want to wear that shirt all the time?

For context, I work in fintech. I speak at conferences, I pitch investors, I work with engineers, I have casual drinks with potential partners, meetings with bankers in suits etc. I also do performance poetry, play Magic the Gathering obsessively, and like to hike and do trailwork. There is no dress code for me.

I am not alone in this. In the co-working space I used to work out of there was a pretty jarring mish-mash of more and less “business like” clothing — gym shorts at hot-desks next to business casual, pantsuits filling up coffee next to yoga pants. I imagine a lot of the people there face the same problem. If I wore a T-Shirt and people showed up to a meeting in suits I would feel like my underdress was a problem (even if for no other reason than making them feel overdressed), and if I wore a business casual collared shirt and pants I would feel stodgy and lame when having a meeting with a crew of hoodied tech folks.

As a general pragmatist I was attached to the idea that I didn’t care how I looked, but now that I was thinking about it — there’s a reason I didn’t spend all my time wearing grey dystopian-utilitarian jumpsuits. Part of the utility of clothing comes from the semiotics of your outfit: what is communicated by your clothing is of real, practical concern.

Semiotics and Clothing

Semiotics is basically the study of things that communicate meaning (literally the study of “signs”). It can be understood in terms of language, but also can apply to almost anything — for example, the construction of an image conveys a lot through symbolism and signalling.

To give an example, why do news anchors sit at desks and wear suits? Why does the text at the bottom of the screen scroll by, creating urgency? This entire image is constructed to convey authority, trustworthiness, and immediacy. In day to day life we also use our clothing to imply group membership, signal status, etc.

Source: Here

These semiotic signals coalesce groups into creating uniforms like the tech bro zip up hoodie ensemble, which derives from Silicon Valley's hero worship of the "drop-out kid genius" archetype.Source: Here

When you look for it, there are plenty examples of this: the seasonal liberal arts wealthy female yuppie uniform that changes year to year (Canada Goose and Uggs, or Burberry coats and Frieze boots, etc.), the frat-bro gym shorts and pinnie, the Brooklyn barista flannel buttoned to the top with beard and heavy rimmed glasses, what-have-you.

Your clothing conveys a message, whether you craft that message or not. So what’s so tricky about work clothing for my generation?

Understanding the Millennial Workwear Problem

The problem that the chambray banded collar shirt solved for me was a semiotic problem faced by a lot of millennials. Our work lives are entirely unlike those of previous generations. It feels out of place to wear collared shirts and pants because we are semiotically attaching ourselves to a group that experienced a totally different form of career. We are not spending our lives building up 401ks in single institution corporate careers. We are the most likely generation to switch jobs, tend to take early career risk in startups that provide low salaries in exchange for the option like exposure to potential payouts from future exits and we work side hustles to augment income based on the ease of creating small scale businesses with the growth of ecommerce (Etsy, Shopify, etc.) and the availability of flexible hours through the gig economy (Uber, Lyft, etc.). We often work remote, engage in multiple projects simultaneously, and have a much higher degree of self-direction in our careers.

In exchange for this freedom (and the possibility of a greater degree of self actualization versus the corporate existence we eschew as cog-like), we trade out access to benefits and ensured financial security. Given that we strive toward different goals and face different challenges than a 1980s lawyer, the semiotic burden of an unrelatable history of professional identity makes collared shirts unfit for our professional lives. At least it does for me (which includes the “new corporate” patagonia vest, chinos, and button down). It would signal inaccurate group identity.Source: Here

Even if you take the other extreme of Silicon Valley’s boy-genius hero worship costume — it still carries a semiotic burden of unprofessionalism to show up to meetings with banks (or, honestly, anyone) looking like you just stopped by after rolling out of your dorm room bed on the way to a class. And I think that the cult of the college drop-out will sour as people realize that one-offs of individuals uniquely early to the coding game from the early nineties through happenstance in youth does not a replicable investment model make (the ability to write code is commoditized), and the new generation of companies exported to public markets from the privately overvalued VC/Silicon valley fugazzi wilt in the light of public reporting obligations when they IPO (in two years you should probably take that early buyout offer from Google because your future IPO is not going to make what you think it will, and in 6 years when Google early buyout offers get less generous because everyone knows you can’t cut it in public markets you should still take it — I could write another article on private market valuations, and I likely one day will). Needless to say, I’m not trying to signal group identity with those guys either.Source: Here

The Solution

The banded collar chambray shirt threaded that needle for me. It carried different, nuanced, semiotics that didn’t push me into either category. It was professional without being reminiscent of an 80s lawyer. It was different and casual without being sloppy. I could wear it to meet banks, billionaires, coders, or friends. It was as suitable in a boardroom as a dive bar, like me, and I wore it all the time because it accurately mirrored that counter-intuitive combination in myself and my lifestyle.

I even spoke to friends with similar careers, and many of them also had that one banded collar shirt that they wore all the time and didn’t know why. I think there is something here about a forming group identity of new professionals that value self-direction over certainty, pragmatism over prestige, and creativity over obedience.

Maybe, if some of this resonates with you, try one out.

Find the shirt:


(Disclaimer: I’m entirely focused on men’s clothing in this. This is in part because it obviously relates more directly to my experience, but is also because I think the semiotic challenges women face in the workplace — especially in our generation — are significantly more complex.)

Further Reading:

Silicon Bro Example

Gallup on Millennials and Job-Hopping

Hacker Noon on Dress Codes

Vogue Article on Women’s Workwear

Millennials and Side Hustles

Semiotics and News Example