Spoiler warning for those who haven't completed the main story.
Yesterday I've unlocked the legend of the east Outfit whitout completing the 90 challenges, i was missing the last 2 herbalist but still got it after completing the last bandit challenge.
I looked on reddit and apparently it's not the first time such thing happens under similar circumstances.
Also in the very bottom of the page about the legend of the east Outfit there is a mention about reports of people getting the Outfit by robbing a female npc on a train for the last bandit challenge at Wallace Station.
I completed the challenge at emerald ranch after buying a train ticket at valentine, robbed a single female npc then ran away.
No clue if the npc has to be female for this bug to happen, but the location it's certainly not a requirement.
In my opinion it's not random as the wiki page suggests but an exploitable glitch.
Here are some photos
Sorry for any mistake I could have made but im new to this and also thanks for reading.