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A headphone amp IS an amp, so you should be able to plug your looper pedal directly into it. You should think about getting a small amp anyway, like a Mustang or Spark.
If you want a good looper, get the Donner Circle Looper. Its actually two pedals in one - a Looper and a Drum Machine. Its easy to use, and built like a tank. Runs about $100.
Yes! Plug it into the output of the last pedal. It will be same as plugging into front of amp, so any modulation/time effects will be colored by any gain stage in the headphone amp.