The winter months can be problematic when it comes to footwear, especially if you live in a wet or snowy climate. Here at the DT offices in the Pacific Northwest, it certainly feels like half the year is ‘rain season,’ which can make dressing for the elements rather difficult. Enter the Tretorn Strala Boot ($60), which is waterproof and will let you traverse the streets without looking like an idiot in full-on galoshes. These low cut boots have all the stay-dry qualities of a classic rain boot disguised in a much more stylish modern silhouette. The boots are a slip-on style and have a rubber traction sole and a fuzzy sock lining to keep your feet warm. Slip them on under your jeans for an incognito way to keep your feet from having to endure the wet and cold weather. Available in black, brown, and olive.