I've done the same blind test with decent but not amazing headphones (HD590) and I could tell the difference all the time as long as the music was slightly comp

I've done the same blind test with decent but not amazing headphones (HD590) and I could tell the difference all the time as long as the music was slightly complex. If loudness was artificially boosted, I had a harder time but could still often tell. I think the sound engineering of the music played a big role and a lot of modern music isn't mixed with complexity in mind. I also go for lossless ;-).