If we're talking MAC lipsticks and glosses, I have these recommendations:
O l/s w/Ornamental l/g (lined with Mahogany or Chestnut)
Honeyflower l/s w/Beaux or Revealing l/g (lined with Cushy)
Coconutty l/s w/Instant Gold l/g (lined with Cushy)
Viva Glam I l/s w/Russian Red l/g (I haven't found a good liner for this, so I don't wear it often)
Desire l/s w/Desire l/g (lined with Chestnut)
Also, I have a partially non-MAC combination that I love for everyday nude:
L'Oreal HIP Charming l/s w/Beaux or Revealing l/g (I line with Cushy)
I know that many people do great combinations of darker lipsticks with lighter glosses, but I tend to keep them close because I'm picky and don't like dark colors getting into my glosses and also don't want to have to keep on hand extra lip brushes for getting the gloss out of the tube. (Lazy me.)