Suggestion for 1st bag ?

Yes, that is the medium. Depending on how big your wallet, sunnies and cosmetic case are, you might want the large Carly instead. I carry all the things you have listed, minus the 2nd cell and SO's stuff, and it fits perfectly, but my wallet and sunnies case are fairly compact. Any more than what I carry and it tends to look a little stuffed.
If you don't like the Carly maybe the Ali? It seems like it would fit everything you have listed comfortably. Since it is last year's, there are only a few left in black or white & you would have to order it from JAX, but I just love that style.
 
I really think you need to go to a boutique and try them on. The Carly is beautiful and very stylish looking, but for some people it can also be a sinkhole. It can be more difficult to locate things in a Carly than in a more structured bag, and you cannot dig around it in while it is on your shoulder very easily.

So it very much depends on what you are used to in a bag and what will feel best for you. A Legacy shoulder bag is more structured but also has a shorter drop. A Bleecker Large Flap has a longer drop and is more comfortable for some people, too.
 
example...


Sunnies(missing) are juicy rather bulky case.



Yes, that is the medium. Depending on how big your wallet, sunnies and cosmetic case are, you might want the large Carly instead. I carry all the things you have listed, minus the 2nd cell and SO's stuff, and it fits perfectly, but my wallet and sunnies case are fairly compact. Any more than what I carry and it tends to look a little stuffed.
If you don't like the Carly maybe the Ali? It seems like it would fit everything you have listed comfortably. Since it is last year's, there are only a few left in black or white & you would have to order it from JAX, but I just love that style.
 
Used to .. denim baggy (lv) speedy (lv) BH (lv)

as you can see i'm used to digging (LOL)

I think i'm looking for something that will fit over the shoulder.
I really think you need to go to a boutique and try them on. The Carly is beautiful and very stylish looking, but for some people it can also be a sinkhole. It can be more difficult to locate things in a Carly than in a more structured bag, and you cannot dig around it in while it is on your shoulder very easily.

So it very much depends on what you are used to in a bag and what will feel best for you. A Legacy shoulder bag is more structured but also has a shorter drop. A Bleecker Large Flap has a longer drop and is more comfortable for some people, too.