Red Cowboy Boots

Robin: Really, red cowboy boots?
Ted: I pull those off.
Marshall: Hey, Lil, if I said, "Ted cannot pull these off" what would I be talking about?
Lily: His red cowboy boots.

—The gang on Ted's Red Cowboy Boots, Everything Must Go

Ted's Red Cowboy Boots, as the name suggests, were a pair of red colored cowboy boots. Ted is under the impression that he can "pull them off", but everyone else thinks otherwise. However, a gay couple (dubbed the "G-CWOK" for "gay couple without kids") believed Ted can pull them off after he asked them because of their "impeccable taste and style"; as Ted brags to his friends, the boots are "G-CWOK approved." He also states that they are "more of a burgundy" in The Wedding Bride.

Ted bought the boots while dating Robin, at the same store she met Nick, after a woman told Ted that he would look hot in them right after he mocked anyone willing to wear them.

Ted enjoys wearing colorful footwear; in Disaster Averted he wears pink rain boots, claiming that "pink is easier to spot from the rescue chopper."

The Red Boots were finally destroyed at Weekend at Barney's when Jeanette burns them. Because this action led to Ted being ready to finally settle down, the Red Boots represent a life that he was finally ready to leave behind.

The destruction of the Red Boots coincided with the destruction of Barney's Playbook, an item that represented Barney's old life.

Ted is similarly stubborn on other fashion choices that his friends mock, such as the frosted tips he insists he is "pulling ... off" in Doppelgangers.