That doesn't sound really difficult. My way to go will need three persons:
1.: model with the Shirt (model)
2.: the drone pilot (pilot)
3.: the drone "holder" (holder)
I would start with the holder holding the drone for the start shot, the drone already powered up and clear for takeoff. The holder walks very gently with the drone back and lift it up. The pilot takes the control and flies the drone like you want it. In the same time, the holder has to run away from the model (and the drone) to be out of the image. If there are other people around, he could just behave like them as soon as he has a certain distance. If not, try to find a way to hide him. Maybe it's a bit easier, if the model only moves very slowly (if he/she should be moving at all) and you speed up the video afterwards.
It may take a few time until the transition from holding to flying is smooth and you should turn off all sensors. It may help to not actually hold the drone, but having it just resting on your palm.
Greetings
Jürgen