The Dryleaf Dane quest is one you should carefully follow while going through the Shadow Realm in Elden Ring. While he isn’t outright crucial to the main story at hand, his quest shouldn’t be missed as he’ll be of possible use to you for assistance and his drops.
How to complete the Dryleaf Dane quest in Elden Ring
To start this quest, you must first beat Rellana. Upon defeating her, progress further until you reach the Highroad Cross Site of Grace. Here, you’ll run into Leda and Hornsent. An item can be acquired around them called the Monk’s Missive.
This message is basically an invitation for a duel against Dryleaf Dane. From here, make your way eastward until you come across the Moorth Ruins Site of Grace. Here, Dane will be awaiting your response. Talking to him won’t do anything. You have to perform the “May the Best Win” Gesture.
You’ll then be transported to an area where you fight him. Upon defeating him, he’ll drop his Hand-to-Hand weapon, the Dryleaf Arts, and his hat. You won’t hear from him again until you progress significantly through the story.
Once you have beaten Messmer, the Impaler, and progressed through the Ancient Ruins of Rauh, you’re going to have to fight Romina, Saint of the Bud. You’ll see a golden summon sign just before the fight where you can invoke Dane for the fight. You don’t have to do this, but he’s there if you need him.
After beating Romina, your next step is to burn the Sealing Tree. This is an irreversible action that acts as the point of no return, so make sure to progress as far as you can with all other NPCs at this point.
At Enir-Ilim, you’ll encounter Dryleaf Dane once more alongside Leda. Once they are all done and dealt with, you can then retrieve the rest of his set, which includes his headgear, chest piece, gloves, and pants.