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https://www.fastcodesign.com/3066599/the-worst-design-of-2016-was-also-the-most-effective
Ballant reiterates that Obama and Hillary's campaigns were rooted in corporate identity design and points out that corporations aren't very popular right now. "Hillary’s branding felt too corporate," she says. "But that also reflected an entrenched reputation she had to push against. And the design, while very good, unfortunately only served to reinstate that fact, especially when you think of how big of a deal it was when the logo was unveiled. It was treated like a Mastercard, Airbnb, or Uber reveal."
While Trump's sloppy branding and (suggestive) logo were written off by the design community as a sign that his campaign didn't know what they were doing, in hindsight it was likely more deliberate than originally thought.
""Like any good confidence man, Trump was highly aware of his audience’s desires," Ipcar says. "Take a look at trumphotels.com. His people understand clean and sophisticated branding; they just chose not to use it for his campaign. There was a clear decision by Trump or someone on his team to make the campaign look like something completely different. It was easy for me, as a Brooklyn-born creative director, to describe the hat as bad design. But the hat was worn. It was simple, unisex, familiar, and practical during a summer of hot crowded rallies throughout the South. Design-wise, it was lazy and loud, but also deceptively brand-aware and unmistakably Trump—a brash and calculated brand extension for a house whose luxury properties are awash in Gotham, understated bling, and lots of white space."