With all the laid-back attitude of the originals, the Converse All Star Rain Boots ($80) are the first we'd actually consider wearing in inclement weather. Staying true to their roots with a simple lace-up design and Chuck Taylor insignias, these rain boots feature a green rubber upper, attached tongue to prevent water from seeping in, corded laces, a reinforced toe, and a durable, grippy sole.
If you're on the job or simply looking to add some outdoorsman chic to your wardrobe, take a gander at the Tretorn Klipporone Boot ($145). This high-top boot features nine eye laces, a combination smooth and textured leather upper, textured, grooved rubber sole, two-tone laces, and a reinforced rubber midsole and toe cap. While they might look good at a country cookout or impromptu fishing session, don't expect to roll around midtown without drawing some strange looks.
Add some simple style to your winter wardrobe with Clarks Originals Wallabee ($130). Based on Lance Clark's original comfort shoe from 1965, the Wallabee is a hand-sewn moccasin featuring a suede upper in one of three shades, plantation sole construction, and a mid-height cut. Their simplicity isn't likely to wear well with dressier attire, but they should go great with plenty of other garb, from jeans to pajamas.