Maya has the matchstick jeans, so I'll let her comment on the those.
Thanks for the update on the floral shirt. My J. Crew doesn't have it--you must have a flagship store near you, Lucky! :) I have been looking for a solid shirt that is the same cut and short sleeves, but it has been difficult to find. All the short sleeve dress shirts I have found have puffy cap sleeves instead of a true short sleeve. Or else they're just plain white or black, which isn't really my thing either. I think I'll take a pass on the flowered shirt then and keep searching for something else more suitable to my style.
I bought the clamdiggers the other day as well and I LOVE them. I'm definitely planning on duplicating these. I've tried on the Caterina top and I thought it was okay. I just ordered the solid geranium colored one, but we'll see when I get it, I'll post pics and ask for opinions for sure.
Looking forward to the pics of you in the clamdiggers--do you roll them or leave them unrolled?