i have both and i think i've used the pst more than the timeless tote. it's easier to get things in and out with the pst cause it's open top. i've actually bought a LV pochette to attach to the D-ring inside the pst and put more valuable/smaller items in the pochette.
i actually like the shape of the timeless tote more, but the practicality of the pst makes me use it more often.
I like the style of the PST better than the timeless. My mom has the PST and I've borrowed it a couple of times... I think it's an awesome bag. Very functional, and is comfortable on the shoulder. My vote is for the PST!