Cowdog? Methinks you mean the beloved Dogcow, Clarus (TN31). (And yes, I have that shirt…)

The best T shirt ever worn by Apple engineers is this one:
http://www.flickr.com/photos/zisa/449899852/

Naturally, there is a saga to go with it.

It seems that a LONG time before System 7.5, the engineer for the Sound Manager wrote a technical note, or gave a talk, and in the process proclaimed, “The Sound Manager sucks. I am sorry. I’m fixing it.”

Rich Siegel, proprietor of BBEdit, took this to heart, and later announced that “BBEdit. It doesn’t suck.” He eventually registered that as a trademark, and still uses it today.

So when System 7.5 was wrapping up, one of the senior engineers, known for his cranky, abrasive nature, came up with the “Sucks Less” slogan. Being a brash Apple engineer, he called a local T shirt place, and was wearing a shirt in a day or two, and passing out copies to the other engineers he thought were most deserving — people who really did make the Mac OS “suck less.” Soon, he had to run a second batch, and a cranky tester suggested the slogan on the back — “We’ve upped our standards. Up yours.”

Well, naturally, this shirt went over VERY poorly with the marketing team, who were aghast that the engineers of the company would not thing that System 7.5 was “Insanely Great” or something like that. I myself got hassled a bunch of times. I’d patiently explain the idea to the marketers, and eventually point them at the originator, who quite enjoyed defending himself.

One of the marketing guys really took it to heart, so when we did System 7.6, the theme was to make the Mac OS suck less. In marketing terms, though, that translated to “Security, Speed, and Stability.” It was, actually, a surprisingly well-selling and well-loved release, even though it meant the end of the road for some older machines. (Snow Leopard reminds me of that release a lot.)

The interesting thing is that the slogan always went over well with the True Believers at MacWorld Expo, who all seemed to assume that we were referring to Windows, and in that respect, it was quite an understatement. Windows 95 had really captivated the world, because it was the first time Microsoft had produced a coherent, top-to-bottom, operating system PRODUCT, but it was riddled with trillions of bugs, billions of compatibility problems, and, most importantly to the Mac crowd, it looked like utter crap. Jaggy fonts, garish colors, and ridiculous error messages.

And, of course, the Registry, which really should have killed Microsoft. It’s a testament to their engineers that they managed to improve it to the point where it’s almost not a problem any more.

No, sorry, there are no more “Sucks Less” shirts available. They were all gone within a month of the printing. I have mine, carefully preserved, and wear it on special hacker occasions, such as Macworld Expo and WWDC.

I myself designed a dozen or so engineer shirts, but none of them has the power of “SUCKS LESS.”

I bought one for myself, my son and my daughter: http://www.insanelygreattees.com/shirt/imamac

“System 7.5 sucks less, we’ve upgraded our standards – up yours” is one of my all time favorites too. Occasionally I just have to wear it at work – and you’d be surprised how often I hear “what’s System 7.5?” when wearing it.
None of the other old skool (or newer) shirts have the same effect.

Other shirts that would have the high coolness factor… well – WWDC staff shirt no doubt. (What would be more appropriate to wear for Windows 7 launch event? Or just any occasion…)

Or perhaps G4 – National Security Risk, or a long sleeved Newton developer shirt, or the Jaguar release shirt.. (took me nearly 7 years to get one:) or the classic Apple Staff shirts.

Some shirts in my huge Apple shirt pile were so used they were falling apart. The Moof shirt listed on that top 10 was among them
http://www.flickr.com/photos/zisa/538876050/