Lessons of a CEO #2 :Fashion Foreword

By Alex, Last updated: 2022-11-01 (originally published on 2016-09-30)

Fashion Foreword

Today’s missives are about startup fashion. The great thing about working in a startup/for yourself/at home/[insert any non-corporate setting] is that you get to decide how to dress. The problem about working in a startup/for yourself/at home/[insert any non-corporate setting] is that you have to decide how to dress.

Now, I went to school in the dark ages when uniforms, in grammar schools at least, were pretty much de rigeur, and my school cursed blessed us with thick woolen uniforms that were a symphony of grey from cap to socks. Uniforms are great because everyone looks awful.

I’m not going to go into what I wore at university so let’s skip forward a few years.


Exit university. Buy 70’s three piece suit from charity shop for first job in city. This was a relic at the time and gave me three years of finger pointing fun.

(No don’t be ridiculous, this isn’t me).

Ignoring the fact that I’m now old enough to have suits that show how old I am (and one day will no doubt be worn as fancy dress with no appreciation for their cutting edge-at-the-time fashion sense), it’s actually difficult to really go too far wrong in a suit. All the better if you can be bothered wearing a tie.

The worst that the corporate world can throw at you is ‘smart casual’ – which for those of you young enough to be CEO of a startup  – is approximately defined as ‘wear your work suit but take off your tie before you arrive for drinks, as opposed to after you have started drinking when you will want to put it on your head’.

How millions of men imagine they look at corporate drinks

And then suddenly you work for a startup. You’re responsible for:

  • Business development (that’s a fancy way of saying your startup needs to sell something – see my future post on how this differs enormously from ‘collaboration’ which is startup for, we won’t buy what you sell but you can buy us coffee),
  • Going to cool startuppy events like RISE,
  • Working with coders and engineers,
  • Working with salespeople, and
  • Presenting to VCs… the list goes on.

And the reason this is on my mind this week, switching job roles, as we do every day at a startup –  means changing clothes – and each change is a constant reminder of how totally cool it actually is to be living in this world of startups. So my rundown this week so far:


Sunday (I wasn’t working – it was my first daughter’s birthday party. She’s 7, not 3. Keep up or see my previous post on the importance of attending your children’s birthday parties). I am the one dressed in a space suit slash cardboard robot:

Monday – I meet Chris (our Head of Legal) in the hallway. Like a pair of startup henchmen we are both dressed in the Zegal-important meetings-to go to-uniform. This is to the startup world, what the pin stripe and bowler hat was to 80s London. Startup men readers out there, be sure you have your jacket and jeans outfit picked out before you incorporate your company.

(A model more handsome than Chris or I)

Tuesday – As I’m working with the coding team today, I decide to wear flipflops and a hoodie. The cliché is not lost on our CTO who looks more sad for me than amused.

Wednesday – We are pitching a mega law firm today so I make some small effort.

(A startup CEO yesterday preparing his sales pitch)

Thursday – And today we are hitting a startup event so of course it is the obligatory jeans, Zegal t-shirt and jacket. All startups jobs should come with the warning that the employee will be expected to wear a black t-shirt with their company’s logo blazoned across it soon after they start and often. Men like me should also have been warned that it is imperative to look good in it.

Well I can’t be good at everything.

Also read: Lessons of a CEO: Nr.1 – Lessons I’ve learnt

Daniel Walker
CEO of Zegal


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