Cannes Lions

Windows Ugly Sweater


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Case Film
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To grab audience attention during the distracting and demanding holiday season, Microsoft Windows needed a break-through approach that felt true-to-brand and tested the bounds of what social media could do. To set us apart from other brands, we asked ourselves: how can we give to our fans rather than demand more of them—and do it in a way that generates brand love and gets people talking?

We needed an approach that fired up our fans while appealing to a broader base—leveraging a culturally relevant approach that would pick up serious traction on social. Our objectives were to reward our fans for the holidays and drive brand affinity within and beyond the immediate Windows community. We briefed our team and challenged ourselves to utilize the brand’s social network to connect with fans in a tangible way.


The answer: double down on nostalgia while being culturally relevant. We designed our very own custom “ugly holiday sweater,” with an iconic Windows twist to surprise and delight social audiences. In designing the sweater, we brought the brand’s rich heritage to life—breaking out the Windows 95 logo, which resonates with long-time users who know it well—for what would be a spectacularly ugly fashion statement. To properly showcase the sweater on social channels, we then captured visually-stunning, original photography of it being modeled in a contemporary and gorgeous environment. After this, the creative would need to soar via user-generated content. We planned to get it in the hands of our most passionate and vocal fans across both channels, as well as select PR influencers with solid ties to Microsoft—and so who were proven advocates of the brand, to show off our creative in their own way.


During the 2016 holiday season, an Instagram post featuring a digital lineup of ugly sweaters branded with iconic versions of Windows logos became a top-performer, generating +309% higher engagement than our 3-month average and a total of 491 comments--the most in channel-history at the time. The positive response to the Windows 95 logo among our social fanbase of techies and PC gamers, who share a personal connection to this OS version having grown up using it, included several inquiries around whether there was a physical version available.

This past year, we were then noticing a trend amongst tech companies trying to present themselves as more humanized through branding, visual language, or their approach to product design. Inspired by this more comforting and approachable way of presenting technology, we created our own wearable tech to remind fans of a significant time in their life in which Windows had taken part.


We started by teasing the sweater with a #throwback post on Instagram and Twitter, featuring a close-up shot of the design and alluding to a “major ‘softwear’ announcement” within 24 hours. The next day, we dropped the sweater with an epic glamour shot and encouraged people to check their DMs for a message from Microsoft. We quickly rewarded our biggest fans, shipping sweaters out to a select few. The UGC came flooding in—and for those who didn’t get a physical sweater, we created an IG story that allowed them to receive a “virtual” version. We partnered with 10 influencers—getting sweaters into the hands of Austin Evans, Jenna Ezarik, Linus Tech Tips, Krystal Lora, and Sam Sheffer, to name a few.

We then selected reputable influencers to receive a sweater, such as stakeholders within the company and influential members within the Windows Insider program.


- Our rollout strategy and partnership with influencers to promote the sweater resulted in a combined total of 242K engagements across brand and influencer channels, including the most engaged-with posts in Windows channel history.

- With 0 paid media spend, we generated a total of 5.6M impressions, 3M of which came from the first two days of the campaign in the middle of December where we’re competing for mindshare among last-minute offers and promotions leading up to Christmas.

- The activation was also picked up by several PR sources, including Mashable, Business Insider, Q13 News, and Geekwire. We even made it to the 1st page of sub-Reddit called ATBGE (“Awful Taste But Great Execution”) where the sweater was praised for its fashionable design.

- 13.4K hashtag mentions of #WindowsUglySweater, the majority coming from fans or press sources talking about the activation on social as opposed to sweater recipients.

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