Windows 95 Holiday Campaign

To reconnect with longtime fans — and introduce Windows to a new generation — we turned one of the most iconic interfaces in tech history into an unapologetically nostalgic holiday sweater.

The idea tapped directly into peak ’90s internet culture, transforming the Windows 95 UI into a wearable inside joke for the internet. What started as a limited-edition drop quickly became a community moment — landing on Reddit’s front page and earning coverage across Mashable, Business Insider, PC Gamer, and regional broadcast.

More than a novelty, the campaign demonstrated how legacy equity can be reinterpreted for contemporary audiences — converting nostalgia into relevance and establishing an annual holiday tradition for the brand.

Creative Director: Tanner Teale
Art Director: Matt Goldberg
Copywriter: Paul McNamara
Social Media Manager: Gabby Cohen

Client: Microsoft
Services: Art Director (Concept Development)

Case Study Film:

How a single, culturally fluent idea converted nostalgia into relevance — and scaled from limited drop to annual brand tradition.