The Design Week Awards 2007 (an event by Design Week Magazine) honors the iPod shuffle for best consumer product design. The result (PDF) was presented by Sebastian Conran of Conran & Partners. He notes that "the Shuffle is a simple, beautifully executed concept...".
There are two things i noticed about the clip that could actually make the Shuffle grip better. First, the spring could be stronger to make the clip attach tighter. Second, the shape of the hooks could be as shown in the image below, interlocking. That way the Shuffle would maybe hold better (that doesn't mean it does not hold ok. It does).

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Apr 07, 07 23:21 CET
About that clip idea: wouldn't thees grips have problems with more unflexible fabric (denim)?
Apr 09, 07 21:05 CET
I guess the grips are happy. But if denim has any issues with the kind of attachement that a shuffle has to offer, then denim should rethink its fabric.