I'm a long time fan of Toms, but I've only ever worn Toms Classics. I purchased these because I needed a nicer pair of sneaker style shoes for travel. I'm a very consistent 8.5 size wise, that's what I wear in Classics so that's what I ordered these in. A few reviews commented that the Del Rays don't stretch like the Classics do, which so far seems accurate (I've had these for five days).They seem to be made out of slightly thicker canvas so I don't think they'll stretch as much as Classics do, but I'd be surprised if they don't stretch at least a little over time. Most fabric shoes do with enough time in my experience. I still went with the 8.5 despite this though because my Classics stretched (over the course of a year or so) to a point where they're quite lose (though not uncomfortably so). I figured even without the stretch I should be fine with my usual size.That being said, the 8.5 Del Reys fit well for me. They are a tad snug, but not uncomfortable. I haven't done any long term walking in them yet, but they wore comfortably through the grocery store yesterday. Length wise they're exactly perfect and I appreciate the slight arch support they have as my left arch tends to fall. I don't have wide or narrow feet so the width is good for me also. I'd say if don't have wide feet and you own Classics that are still fairly snug after a good amount of wear, you'll probably need to go a half size up in the Del Reys. I'm very happy with this purchase and will definitely be buying this style in the future.