We've already discussed classics like Top-Siders and white bucks. This week, we're presenting the season's best shoes, all for under $100.

• All of Keep's products are cruelty free.

Somewhere between a boot, a sneaker and a proper dress shoe resides this cotton canvas chukka. Lightweight and nimble, they're incredibly comfortable yet durable enough to last you well into the fall. But you'll appreciate them most when the mercury's pushing 90 and the last thing you want are bulky, padded leather shoes. Crafted by Keep shoes, the California company started out by selling streetwear shoes to the ladies who weren't looking for pink shoes. Their simple, monochromatic styling led to so many men asking for some, that the company now makes nearly all their shoes in unisex styles and sizes. $64, by Keep