There are Keisei Skyliner trains which leave NRT T1 at 21:49 and 22:30 (3 minutes later from T2) and arrive in Nippori at 22:28 and 23:09.

From Nippori take the Yamanote or Keihin-Tohoku Line to Hamamatsucho (17-18 minutes). Then the monorail (timetable) to HND International Terminal. It will be quicker than the Keikyu Line via Shinagawa.

Make sure to buy a Suica or Pasmo at NRT so you don't have to buy separate tickets at interim stations.

I don't know how busy immigration will be at that time of the evening but you should be able to make the 22:30 from NRT unless your incoming flight from North America is very late.