Caught between Canada's lukewarm autumn and paralyzing winter, November is the period of time when we receive cold, overcast days and heavy downpours. It calls for a special type of footwear—something not as heavy-duty as winter boots, yet more appropriate than the cheap pleather booties you keep convincing yourself are waterproof. Stylish yet practical waterproof gear is hard to find. Cue the new Hunter.

Hunter Original Fall/Winter 2014. Clockwise from left: Womens’ nylon down jacket, $625; clear shopper in burgundy, $365; high heel Chelsea neon sole boots, $325, all available at ca.hunterboots.com.

Ever since Kate Moss trudged through the mud-soaked grounds at Glastonbury in 2005, Hunter merchandise has been seen on everyone, from your next-door neighbor to the likes of Sarah Jessica Parker and Angelina Jolie in Mr. & Mrs. Smith. The iconic British label, founded in 1856, is known for its trusty, high-quality wellies originally made for troops in the flooded trenches of World War I. Hunter has been in the process of reinventing itself from a quiet heritage brand into a dynamic fashion-minded one since 2009, when the company added leather boots, fashionable rubber boots and handbags to their roster of products and partnered with Jimmy Choo for a line of designer rain boots. Now, with Alasdhair Willis at the design helm, they are well on their way. Willis, founder of two creative agencies and a trendy furniture company, as well as a former publisher—not to mention the husband of powerhouse designer Stella McCartney—was appointed creative director in 2013 and since has injected the brand with a dose of youth and modernism through his interpretation of functional performance wear. Ambitiously going after a spot in the industry as a top fashion retailer, Hunter launched its ‘Hunter Original’ sub-brand at London Fashion Week for Fall/Winter 2014, implying their permanent tenure at LFW by showing again this past September during the Spring/Summer 2015 presentations . Under Willis and his vision for Hunter’s reinvention, product categories have expanded to include more innovative designs in apparel, footwear, knits, and accessories. Classic trench coats have received rubberized and glossy coating upgrades, trendy Chelsea boots are elevated with high heels and neon-cleated soles, and basic shopper tote bags now have not-so-basic in vinyl and leather finishes.  And yes, the original Wellington rain boots with its notable moustache detailing are still in the mix, their ubiquitous design left untouched. Forget waiting for rainy day. You'll be looking for an excuse to sport these new duds as much as possible. For more fashion news, visit our Style Desk blog.