sony walkmans.. whats the difference??

thinking about purchasing a sony walkman NW A55 for a hunned fiddy..

im told its not worth it unless you have the ability to really sit down and listen, which i do lol..

i own over ear xm4s and a samsung s25,

will plugging the headphones into the jack of the walkman be a day and night difference?? orrr am i better saving for something else??

i do understand codecs aswell just curious about the advantages of one of these bad boys..

thanks