Leaving aside the mountains of analysis one could produce on the differing styles of these two men, let’s focus for a moment solely on the pants. Trump doesn’t often do business casual, and when he does, his go-to choice is khakis (always topped with a navy blazer), but never, ever jeans.
Obama certainly wasn’t the first POTUS to sport the all-American denim look. Jimmy Carter and Ronald Reagan both favored dungarees during their off-duty hours. Bill Clinton often sported jeans, sometimes for work weekends. George W. Bush might have famously sought to bring back formality to the White House after the rowdier tone of the Clinton years (“There will be no blue jeans in the Oval Office,” a Bush aide “sniffed,” according to a 2001 Time magazine story) but he, too, sometimes wore the casual look, even for public appearances with world leaders.
According to the available photographic evidence, Trump might have a had a brief and unserious fling with denim in the late 1990s — he’s seen wearing them in a scant few shots from the era. But we can’t find proof that Trump has worn jeans in the past two decades. His longtime butler (hey, who doesn’t have one of those?) recalled that Trump once owned a pair that he wore exclusively for ski trips “out West.”
“When the skiing stopped, the jeans disappeared,” Anthony Senecal told BuzzFeed. “You’ll never just see him in a T-shirt and jeans, he’s going to be in a suit.”
And first lady Melania Trump underscored Team Trump’s formal branding in a 2013 interview with ABC News, in which she called her then-7-year-old son, Barron, “a mini-Donald.” Like his dad, he favors suits and ties, she said. “He’s not a sweatpants child.”
Such jeans rejection puts Trump out of step with the average American: Statistics are hard to come by, but some data suggests that 96 percent of Americans wear them.
Lauren Rothman, a Washington-based stylist and author of “Style Bible: What to Wear to Work” notes that an Everyman look isn’t exactly the image that Trump seems interested in projecting. “The rest of the world might be adopting more casual workwear,” she says. “But that doesn’t play into his narrative.” And, she says, Trump has found looks he feels comfortable with — and those clearly don’t involve experimenting with denims cuts. (Remember the mocking of Obama’s “dad jeans”?) “We have seen a more guarded style profile from him — it’s versions of the same thing, every day,” she notes. “There’s a confidence that comes from a uniform.”