TMZ.com: President Donald Trump Wears $10K Cowboy Hat in Oval Office - DONALD TRUMP THE GOOD, THE BAD AND THE EXPENSIVE ... Wears $10K Cowboy Hat In Oval Office - TRUMP'S WILD WEST MOMENT - Donald Trump went full "City Slickers" in the Oval Office ... when he slipped on a super pricey cowboy hat in front of some rodeo pros.