I think the small one is more then enough, I had a a deep pink with purple hues one with purple leather trimming, but I ended up selling it, it just wasn't worth it, and it was too easy to scratch for me to deal with. I don't think they have a design currently worth it, but thats just my opinion. I did order teh pocket calendar during the PCE because that would fit my needs while I am thinking of getting a similar paul smith one next year if I like that size. Maybe get a cheap one in the outlet and see if you like the size? It all depends on you, if you love the design and it fits your needs. For work and school and life the small one fit okay, and it fit into my smaller bags which was a plus.