Even with 256 kbps AAC or other lossy formats, it's still worth considering an external DAC. I also have a lot of music in lossy format and listening to them on my desktop (Oppos HA-1 and Audioquest Nighthawk) brings much more enjoyment than listening on the iPod Touch (using the same headphones). For me, it was worth it going from iPod Touch ($300) to Oppo HA-1 ($1200) using the same headphones.
As a previous post mentioned, you may not get the full benefits of a higher end system, but you do get noticeable and positive improvements. I often listen to these same lossy files on my speaker system, and it is even better (Aurender X100L, Bryston BDA-2, Octave V70SE, Dynaudio S3.4, Nordost Heimdall 2 interconnects and speaker cables, Wireworld Eclipse 7 power cords, Running Springs Audio Elgar power conditioner).
EDIT: Also note that it's not always the format that determines the quality of the music. There are a lot of music in lossless (FLAC, AIFF) format that sounds awful. If your music is good, even lossy format can sound good; it just wouldn't allow you to get the most out of the music. One strategy is to pick out some of your favorite music that sounds good, and buy the CD or download it in lossless format (or high resolution format).