一些想法：

class Model(model.Model):
    _image=models.ImageField(upload_to='folder')
    thumb=models.ImageField(upload_to='folder')
    description=models.CharField()

    def set_image(self, val):
        self._image = val
        self._image_changed = True

        # Or put whole logic in here
        small = rescale_image(self.image,width=100,height=100)
        self.image_small=SimpleUploadedFile(name,small_pic)

    def get_image(self):
        return self._image

    image = property(get_image, set_image)

    # this is not needed if small_image is created at set_image
    def save(self, *args, **kwargs):
        if getattr(self, '_image_changed', True):
            small=rescale_image(self.image,width=100,height=100)
            self.image_small=SimpleUploadedFile(name,small_pic)
        super(Model, self).save(*args, **kwargs)

不确定它是否能与所有伪自动 django 工具（例如：ModelForm、contrib.admin 等）配合使用。