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I'm using Wordpress.SE a lot in the moment and every time I visit the site I ask myself where I'm actually at.

Sure, this is very subjective but in my opinion the design of the site does not reflect the modern software which Wordpress really is. Sure, the design with the book press should represent the main intention of the software: blogging, writing and publishing articles.
But in the last years Wordpress developed from a simple blog engine to a multifunctional CMS that powers not just blogs but also portfolios, business showcases and much more that in fact has nothing to do with writing.
In my opinion the design would rather fit for Writers but not for a modern web software.

My suggestion would be a clear and modern redesign. Maybe a little bit like the Webmasters site but without these squeaky colours.
Other examples for modern design: Apple, User Experience or Android Enthusiasts

Edit: this is not a duplicate of New Profile Design as this topic addresses the profile design while I'm speaking of the overall design of the site. But maybe it could be linked together as it seems that both topics rely on basic CSS updates.

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    I - pretty much - couldn't care less about the design, but there are a lot of functionality possibilities that could be attacked and would come in very handy. So functionality, before design! But that is - of course - only my personal opinion. – Nicolai Jul 30 '15 at 13:29
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As a personal opinion the newspaper aesthetics are a underwhelming fit not just now, but were even back when it was just made.

Unfortunately design isn't something that is (or can be) part of community driven SE processes. In the end there needs to be a professional designer, doing this work, getting paid for it by SE, and balancing it against all of the other work needed in the network.

Business decisions. I wouldn't hold my breath.

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