They´re cool, but they´re in most of your fits. Some new footwear would do you well imo.
Definitely. I've got Jack Purcells, but it's winter and they're canvas. They are also all-white, like the CPs. I've got my Momas too, but they don't really work with a lot of what I wear right now since many of my fits consist mostly of black and grey.
Not really sure what exactly to get. However, it's also pretty important to remind myself that I probably shouldn't spend any more money on clothes for a while. I've been really fortunate to find and afford several really great items (e.g. ToJ, CPs, sweaters, S2A jacket+pants) at really great prices over the past 5 months; that's not a pace I could reasonably continue at this moment.
I'm keeping my eyes open for things I might eventually want to buy, but it's doubtful I'll actually purchase anything for a bit.