Best rear basket configuration?
 

The ones that hang off the side or the ones that sit on the rack?

Would it be better to have two smaller baskets on either side or one larger one on the rack? Or just one on one side?

I've been looking at these Basil ones: one and two, mostly because I can get them at my LBS and don't have to buy them online. Feel free to suggest others that you really like though.

On a regular day I'll usually be carrying a medium-sized purse, a u-lock, and probably a rain jacket and some shopping along the way. When class starts up again I might end up bringing a backpack with a laptop, books, etc, as well.

Suggestions?

Do you have a step-through frame or a diamond frame? I ask because if you have a diamond frame and are fairly short, it can be hard to swing your leg over a basket mounted on top of the rack. I used to use a milk crate zip tied to my rack, but I had to step over the top tube to make that work. If you have a step-through frame, then that's not so much of a concern.

These folding baskets from Wald might serve your purposes nicely: 582 Rear Folding Basket - Waldsports. They fold flat against the bike when not in use.

I have a diamond-frame. I'm not too short but I can see myself thwacking my ankle a rear basket...

I've heard of those. I'm not sure if I want folding ones though... they just seem like they would be heavy if not in use. Otherwise they look quite nice though.

Keeping weight located with a lower center of gravity is the way to go for most IMO. But if your only carrying light loads such as bread or a book or two, the rear basket may be ok

OP, if you like those side-mounting Basil Bottle baskets and you can get them at the LBS, ask if you can mount them on your bike+rack and ride around the parking lot first to make sure your heels aren't going to hit them while you pedal.

For a diamond frame bike I would strongly suggest the side mounted ones. It can be tough enough to keep the bike upright when the weight is lower, trying to dismount and move the bike around loaded up with stuff in a "trunk" basket would make me think it would be even tougher, but I've never had a basket there, so it could be just fine.

I like the Wald 582's because I like being able to fold them up when not in use (it at least gives me the psychological feeling that my bike might be spry). But if you are pretty committed to the basket/utility cycle setup then sure, go for whatever is lighter.

I will say though that it's nice not having to clear the basket when mounting the bike when it's not in use.

Best? Like German made stuff?

Klick fix Rixen & Kaul, KLICKfix Adaptersysteme Fahrradzubehör, Solingen, Taschen, Körbe, Werkzeug

and Ortlieb make rack top QR mounts to use.adapt as suits you. the wire mesh basket you linked to should be fine ,

the QR feature would let that mesh Basket pop off easily , to bring in and fill with your shopping.