I couldn’t do a collection of travel movie costume ideas without at least one Wes Anderson film! It’s hard to pick a favorite, but The Darjeeling Limited feeds my train travel obsession (and that luggage!), as well as some featuring seriously wanderlust-inducing backdrops.
Whichever brother you’d like to be, start with a suit and accessorize from there:
Vintage wood box (you’ll have to stencil on your own skull and crossbones, but no one will touch your candy)