I ' d go with crowderhigher floor and probably ceiling with Hilton ' s situation <| sep |> Disguise Self only requires an Int check if they ' re investigating the outfit to decide if you ' re really what you appear to be . Otherwise it works for casual observation . However , the illusion is rather static so I wouldn ' t give advantage or disadvantage for it , maybe just a X to hiding . The Cloak of Elvenkind does disadvantage because it ' s active camouflage , constantly changing colors kinda like Predator . Flying with excess cargo whether items or another person is not going to pan out well . You ' d follow the rules for carrying capacity and encumbrance . In most cases you ' d probably be reduced to 5 feet of movement , barely hovering along . That ' s why the spell lets you cast higher and make other people fly too .