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The Sisterhood of the Traveling Khakis
Dockers gets the biggest name in Khakis to be their new Brand Ambassador. I asked for analysis and reactions about the campaign from Tara Lawall, a Chief Creative Officer and Emmy-nominated writer, and then I also asked my dad, who is squarely in the target audience for this.
Jack Westerkamp
September 21, 2026
“Target audience” this, “conversion rate” that, “brand truth” this blah blah blah. Give Jim Harbaugh the keys to the brand and get the hell out of the way. There is legitimately one person on planet Earth associated with khakis, and it’s current Los Angeles Chargers Head Coach, Jim Harbaugh. So, Dockers is making Jim Harbaugh their Official Khaki Ambassador.
This was created by OBB Media and their content studio, bolded. This crew has been really crushing it. Look them up. They won a bunch of Cannes Lions this year.
Anyways onto the Harbaugh lore with khakis, making this make a lot of sense.
He famously stopped on the side of the road to buy $8 khakis at walmart back in the day after his wife threw away one of his pairs. This guy has been wearing khakis for decades and he’s kinda unintentionally hilarious so as a result you get a massive “inside joke” between adult males that spend their weekends watching football.
Although the “Jim Harbaugh like khakis” thing has been a thing for about a decade, I think it’s been rarely leveraged by brands. At one point, Jim donned a Lululemon pair of khakis he received as a gift. Jim, like many others, appears to have moved on from the Lululemon uprising that dominated finance offices from 2017-2024.
So, Jim hasn’t had an official khaki. Until now. (subscribe to see the rest, it’s $0)