March 10th, 2026
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A snappy answer when asked about dressing casually at IBM

I noted in the past that Microsoft engineers had trouble fitting into the IBM corporate culture when on temporary assignment at IBM offices in Boca Raton, Florida. In particular, they struggled with so-called “security violations“. I noted that one such category of security violation was “wearing shorts to work.”

Bearing this in mind, you may appreciate this brief incident.

One of the Microsoft developers beeped his badge to enter the building while wearing his usual shorts and sneakers.

An IBM employee sarcastically asked, “Dressed a bit casually today, huh?”

The Microsoft employee replied, “Oh no. I dress like this every day.”

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Raymond has been involved in the evolution of Windows for more than 30 years. In 2003, he began a Web site known as The Old New Thing which has grown in popularity far beyond his wildest imagination, a development which still gives him the heebie-jeebies. The Web site spawned a book, coincidentally also titled The Old New Thing (Addison Wesley 2007). He occasionally appears on the Windows Dev Docs Twitter account to tell stories which convey no useful information.

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  • Daniel SchallMicrosoft employee · Edited

    Reminds me when I did an internship at IBM Germany (Böblingen) in Software Engineering, around 2008.
    My boss was working all around the globe, mostly meeting customers, rarely in the office.
    When I asked him prior to my first day, what to wear, he was kinda confused and told me "umm, business.. I guess..?".

    So, first day, I show up in a suit and tie, some other fresh interns already in the lobby, of course dressed in jeans and shirt.
    Everyone was eyeing me.
    I introduce myself to the front desk and say shyly: "Hi, I'm starting an internship today..".
    The...

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  • Rob PavezaMicrosoft employee

    My second job out of college, I wore shorts to work. I was a dev at a marketing agency in Arizona and it was the summer.

    One of the founders asked me: “Rob, you want to work at Microsoft one day. Do you think they wear shorts to work there?”

    Admittedly, when I’m at the mothership now, I generally wear pants instead of shorts, but that’s because it’s cold in Redmond most of the year….

  • John McCormick

    I remember back in the time I worked at Microsoft (11/93-03/97) you were always in a suit. Did that ever change?