OK - lovely list of names, sometimes it is so hard to narrow it down as there are so many gorgeous ones to pick from!
Lennox Reuben Olivier - Like Lennox but not Len, love Reuben but getting popular, love Olivier but only as a middle name
Asher James Nicholas - Love love love Asher, James is a bit meh IMO, likewise Nicholas
Miles Gideon Silas - Not too keen on Miles, love Gideon and think Silas is ok.
Girls
Tallulah Georgina Bo - love Tallulah but not brave enough to use it, Georgina is ok, likewise Bo
Emilia Gabriella Quinn - not keen on any really
Stephanie Juliet Coco - love Juliet and Coco, Stephanie is ok
Nickname wise - you could have Lex for Lennox (thus avoiding Len!), Ash for Asher, Milo for Miles or Miley, Tally or Lula for Tallulah, Emmy or Mila for Emilia and Steph, Effie or Nie for Stephanie.
I would also suggest having Juliet as a first name with the nickname Ettie.
If it was me, and to go with Chester, I would have:
Asher Reuben Olivier or Asher Reuben Gideon
and
Juliet Stephanie Coco