In 2018, Microsoft first showed off the “ugly sweater” in the style of Windows 95. Many users liked it then, but the company sent such sweaters to only a small number of fans. 2019 saw the introduction of a Windows XP-style sweater, but it was also available in limited numbers. In 2020, a Microsoft Paint sweater was added to the collection, but the main thing is that everyone can buy sweaters in the company online store.

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