I´m using django-photologue (with 1pinax) and want to scale images to a box (100px x 100px). Portrait images should be scaled to height 100px and the width should be filled with a color.
django-photologue: How to scale image to box and fill background
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You can use PIL with a transformation matrix. For example, the following function resize and crop in a single operation. Personally I prefer to crop rather than fill it with a color, but you can adjust it to your needs.