Classic vs. Funky

I often have trouble deciding if I want to take the classic (the safe route of choosing a classic style) versus choosing a funky style I'm momentarily in love with. Knowing myself, I probably will get bored of the funky style; however, I can't stop thinking how great this bag would brighten up my look. But for practical reasons, perhaps classic will always win.



vs.




Or a happy medium…



What do you usually go for? The classic style or the bold, colourful, pattern of the moment?