Lea would dress up as a dullahan, or at least have the same striped pattern around his next that his legs do.
Static would be wrapped in bandages heavily and would be a mummy! Well, except for his face. He need to eat food and stuff.
Andri would just go as himself. He’d wear one of the cute outfits that he likes to wear sometimes.
Gerrick would probably dress up as one of his friends. Something like… yellow sweater, glasses, and blue shorts.
Nall would want to go as some sort of blue/red combination from Tron.
And Vaiyu would be his programmer! A basic relaxed office outfit I suppose.
Makoto would dress up in a jinbei with an ocean pattern on it!
Esther would like to go as Primrose from Octopath Traveler or Throné from Octopath 2.
Chal would dress up in some kind of steampunk suit, especially if it would have a charming little cap with it!
And Jasper? Jasper would dress up like some sort of yakuza boss. He’s into the relaxed but intimidating sort of style!

Lea and Makoto would be in a race to compete with each other for first place, but Lea would manage to slide out of the door. A smug grin on his face no less, immediately followed by Makoto with a disgruntled scowl.
Static would then follow suit, leaving only the tricksters in the plane.
Vaiyu and Nall would start making their way to the open door of the plane, but Gerrick would already be there with Andri following behind him. Being devious, Gerrick would let one rip and say “well, I guess you two need to jump now.” Before jumping out of the plane. Andri would follow immediately after him because he was directly in the way of the cloud Gerrick let out.
Leaving only Vaiyu and Nall, who at this point, are just going to jump out together and take their time. Vaiyu had to do a lot of convincing to get Nall to go skydiving.

Gerrick is a handyman.
Nall is a college student, but he helps around his campus with menial tasks.
Vaiyu works at a club as a bartender, it’s a pretty relaxed job because of the reputable nature of the patrons.
Static is a wrestler, but he also helps Lea with his job by taking photos.
Lea’s job is something like a middle-man for instrument collectors. He’s like the door dash guy for the instruments. Although he does have his own personal collection he tends to on his own time.
Andri is at the same campus as Nall, but Andri is one of the more reliable models for any of the students in need of a model for the clothing they make for their course.
Makoto is a professional surfer, he’s always loved the ocean, so it was a dream come true for him.