10. Windows 8

Year original logo introduced: 1995

Year logo re-designed: 2012

The Microsoft Windows brand has always carried a lot of weight in its recognition, even through the carious iterations of the operating system and their representative insignia. So when the logo for their new OS arrived-by way of hackers dumping a leak, no less-macro designers and Microsoft devotees were ready for another step toward innovation. What they got was a lopsided, simple, jarringly bright logo that failed to inspire.