Dressing for the transition between seasons is always fun but rarely easy. There’s the matter of choosing between shorts or pants, light colors or dark, jackets or no jackets – and then there’s footwear. Choosing a pair of shoes ain’t easy because if it’s too cold for flip flops and too warm for boots, what are you supposed to do? The answer: Invest in a pair of these stylish transitional shoes to take you from summer to fall in serious style.