You might want to look at #4115, which adds a thumbnail filter:
http://code.djangoproject.com/ticket/4115
Using this, instead of making multiple copies of the image when you
upload it, you simply upload the original highest-quality image. When
the thumbnail filter is used in a template, it checks if an image
exists with the requested dimensions, and creates the image if it does
not already exist. It can also generate the image tag automatically
for you and avoid any distortion.
The patch places the files in "django.contrib.thumbnails", but you can
actually put the thumbnails directory anywhere. Just add it your
INSTALLED_APPS (that would be "myproject.thumbnails" if you placed it
in "myproject/thumbnails/") and {% load thumbnails %} will load the
filters. Do read the docs (the docs are the last file in the patch).
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