What: Tretorn Skerry boots

Where: Plenty (various locations)

Price Tag: $75

Why: The Tretorn name is synonymous with both courtside and dockside activities, but has recently made the transition to streetside adventure with a splash. Robson, Granville, and West Broadway are suddenly teeming with bold splashes of canary yellow; pant cuffs are no longer getting soaked; and puddle jumping isn’t just for kids anymore—and it’s about time! There’s nothing more annoying than new spring shoes getting trashed before the season even hits. These rubber boots are comfy, classic, practical, and hip. The shorter style means easy on, easy off, and they’re perfect for tucking pants into. No matter what you pair them with, they’ll be the predominant accessory, so streamline the rest of your look to avoid looking silly. They come in black too, if your style is more subdued. Spring showers are still in the forecast; at least these cute boots will keep you singing in the rain.