Though you may not have guessed it from his glitzy upbringing and suit-and-tie uniform as co-head of the Trump Organization, Donald Trump Jr. is a rugged, game-hunting, flannel-loving lumberjack at heart—an anti-elitist elitist who, like his father, has convinced many middle-class Americans that he’s more like them than not.
Sure, he’s a real estate heir whose public speaking fee is an estimated $50,000, but his rough-and-tough personal hobbies (shooting endangered animals in Zimbabwe and riding A.T.V.s in the Catskills) and L.L. Bean weekend wardrobe reveal the real Don Jr.: an uber-masculine bro who would retreat into the woods and stay there, surviving on a strict paleo diet, if he didn’t have to uphold the family name.
This is certainly the image Don Jr. telegraphed in a recent New York Times profile, headlined by a photo of the president’s eldest son—dressed in a plaid orange shirt, faded dad jeans, and mountaineering boots—sitting awkwardly on a large tree stump and doing his best “pensive in nature” expression (evidently, he does not share his sister’s modeling skills).
While the image is consistent with what we know about Don’s out-of-office lifestyle from old photos (here he is during a 2011 hunting trip in Africa, knife in one hand and bloody elephant trunk in the other) and old interviews (he has spoken publicly about preferring fishing to golf, his father’s favorite sport, as far back as 2004), it’s also beneficial from a political standpoint.
Don Jr. is not as close to the political spotlight as his sister, but as the president’s son— one who appealed to heartland conservatives during his father’s campaign— he is seemingly pushing a man-of-the-people image, in the same way politicians like Mitt Romney, Jeb Bush, and John McCain have done in the past.
Casual dress can make a political candidate appear more approachable and personable—particularly when worn in traditionally formal settings, like at a campaign rally.
Romney wore dad jeans and white sneakers so often during his 2012 campaign that he became a normcore meme. During the 2016 campaign, GOP candidates Jeb Bush, Marco Rubio, Ted Cruz, and John Kasich all wore cuddly zip-collar pullovers—the official “Off Duty” Pol look—on the stump. John McCain developed a reputation for dressing like Mr. Rogers, as the Washington Post put it, during his 2008 presidential campaign. Rick Santorum’s sweater vests telegraphed a similarly warm-and-fuzzy, regular-guy image during his 2012 run.
Don Jr.’s off-duty look is more Outdoor Bro than Cuddly Dad, but it makes him seem equally approachable to his target audience. It’s not an easy look for a Trump to pull off: his father looks doughy in the Presidential leather flying jacket.
Don Jr.’s brave sortie in flannel sends a message to the hypermasculine, old patriarchal guard that they are not, in fact, a dying breed. On social media, he may have been mocked for looking ridiculous, but Donny wants the Trump diehards to know he is their tree trunk-straddling, shotgun-wielding ambassador, eager to fight for their interests and make sure they remain relevant. One down-home, flannel-wearin’ shirt at a time.