Basically, I am creating a lookbook for a client that will look similar to this link text. I am looking for a CMS where the client can upload images, update copy, and it generates a new lookbook for them.
Joomla is perfect for this type of website... www.joomla.org
Well, almost any CMS would facilitate that, although a lot of template work would be required. But I would consider the problem to be one for a gallery system rather than a CMS. Something like gallery.menalto.com could do it if you added a number of custom fields and built a completely custom theme.
I would actually like to point you to ExpressionEngine (www.expressionengine.com) as it is rather a robust Content Management Tool.
However, in my honest opinion I would highly suggest you use an MVC framework that will allow you to create a custom solution without having necessarily repeat all the common things such as authentication, templating, etc. This day in age, I believe it would actually be more beneficial in the long run to create a custom solution as a CMS will take you as far as it will allow you unless you can extend the system with plugins/modules or you extend it yourself.