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.