This requires you to customise your character with the correct module. Press triangle on a song in the song selection screen to enter the customisation for that song. Go into modules, and the recommended module will have a star with the word "recommended" inside.
For the first song, "Weekender Girl", the recommended module will be called "Pansy". For the second song, "1/6 -out of the gravity-", the recommended module will be called "Out of the Gravity". Both outfits will cost 750 VP each to purchase; easily obtainable considering you'll need 3939 for another trophy anyway.
Once you have the module, go into accessories and purchase any accessory for the trophy. The cheapest item is in the "Face" section, costing 100VP for Silver Rimless Glasses. The trophy will pop as soon as you have the module and an accessory equipped.