Well I'm put it this way *warning about to break the cardinal rule of women* , but I'm about a size 16-18 and I have a belly and my arms are kind of on the larger size. I have one of the older East/West duffles which I think is around the size of the first one you picked out and I carry it proudly, but sometimes I do feel a little funny walking around with it. It fits right under my shoulder and is comfy, but I sometimes wonder if I look funny to others carrying it.
But in the end my love of Coach over powers any voices of doubt in my head and I wear it because I love the bag so much.
So if you really love the first one and are worried, I wouldn't be.
I like the carly better especially because the size is more practical for me, I always go for bigger bags. I think the carly is a great design and I just think it's a better looking bag overall.
I love the carly, but the first might be more versatile with the khaki/black combo. Depends on the rest of your collection, but my official vote is for the Carly
I'd definitely go with #2 the Carly.
When the legacy stuff first came out I RAN to the store to buy ... wound up going home empty handed .. just didn't like the color combo in person.
I also think the Carly would be great as far as everyday worry free enjoyment!!