I haven't been able to use it much yet. The lining is alcantra, I believe, like my Viva Cite. I use that bag (VC) all of the time for several years and have never had trouble with the lining. I change out my bags all of the time, but they never get dirty inside. The Hampstead, while technically an open tote, does have a clasp closure and it cinches up at the top with two snaps. While it's under your arm, you shouldn't have any difficulty. As I said in my first post, it needs some breaking in time, because the leather is very stiff. I think it will be fine for my needs. What kind of lining does the Damier Speedy have? I thought it looked the same as the Hamstead.
The bag was so stiff when I brought it home (because it was stored folded) that I filled it with books and hung it on a clothes rack for about 24 hours and it straightened out.
--Judy