In its effort to make itself cool again, Microsoft and ad agency Crispin Porter & Bogusky have launched a

Microsoft clothing line

called ‘Softwear by Microsoft.’

The line of geek t-shirts has a 1980s retro flavor and includes MS-DOS t-shirts as well as a Bill Gates mugshot t-shirt, seen above.

Microsoft says the line “taps the nostalgia of when PCs were just starting to change our lives” and will “showcase the DOS days of the software company that now connects over a billion people.

To give the line of clothing some ‘street cred‘, Microsoft has teamed up with rapper Common, himself a child of the 80s, to promote its new softwear wares.

So will it work?

I’m not so sure. Crispin Porter & Bogusky has a hard task in trying to make Microsoft ‘cool‘ and the agency’s Seinfeld ads were, on the whole, not received very well.

While I understand that Microsoft needs to maintain its brand and try to make it more relevant and respected, I personally get the feeling that Microsoft is trying too hard.

Getting into fashion and throwing an extravagant launch party seems odd given the company’s stated plans to cut back on marketing, as Joseph Tartakoff of the Seattle Post-Intelligencer points out.

In my opinion, Microsoft has things in reverse. It has to create a brand that people want to associate with before they’ll wear a Microsoft shirt; the shirts aren’t going to drive a desire to associate with the Microsoft brand.

As much as I have fond memories of writing my first BASIC program on a 286 powered by MS-DOS as a young kid, I have no intention of wearing a MS-DOS tee.

Do you?