On a door or swinging window the loose edge of the weatherstrip should be closer to, but not touching, the window or door stop. Or, In other words, on an inswinging door, the loose or moving edge should be closer to the outside of the building.
On a double hung window, the locations for weatherstripping include the jambs, the head and sill, and the meeting rail.
On the window jamb, always locate the "seal" or the loose edge of the weatherstrip as close to the parting bead as possible. This will reduce the air infiltration at the meeting rail. (The parting bead is the vertical strip of wood that separates the upper and lower sash.)
When weatherstripping at the head, sill and meeting rail of a double hung window, attention must be paid to whether there is enough room for the weatherstrip. If the weatherstrip prevents the window from closing all the way, it could actually increase air infiltration. Also, the spring bronze weatherstrip used at the head, sill and meeting rail of a double hung window will tend to fight against the sash lock. It may be necessary to trim the bottom of the lower sash and/or the top of the upper sash to make room for the weatherstrip. In addition, it may be necessary to make space in the meeting rail if you wish to install spring bronze weatherstrip there. Position any spring bronze weatherstrip installed in the meeting rail so it does not catch dirt. It is possible that it is better to weatherstrip only the jambs with spring bronze weatherstrip.