Material: Leather, UggPlush Recycled Wool & Lyocell Blend, Foam, Elastic Gore, Textile, Molded Shell  | Sizes available: 7-14 | Fit: Wide | Colors available: 2

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5. Best Budget: Sorel Cheyanne Metro Lace Boot

Think of these boots by Sorel as the lightweight, nimble, nifty, and streamlined version of men’s duck boots. What stands out here are the spacious eyelets and the hiking-boot laces that thread them tight, supporting your ankle with each step. The eyelets bring a simplistic and relaxed aesthetic to the shoe. And the molded footbed brings reverse angle grippy tread and bold branding.

While they would do well in a rainy city (Seattle, looking at you), the tread means they’ll handle little outdoor pursuits if pushed to it. They come with 100g of interior insulation, giving softness and warmth aplenty. 

By merging the everyday comforts of a sneaker with some of the capabilities of a boot, these make for a nimble winter city ally.

Material: Leather, EVA Rubber, Insulation | Sizes available: 7-10.5 | Colors available: 2

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6. Best Season-Transition Sneaker: Studio Nicholson 

If you’ve ever taken an impromptu showering from a passing bus, car, or HGV, you know how grim a rainy city can be. To help negate the woes of a wet metropolis, these Studio Nicholson boots have a little waterproofing from the rubberized sole that creeps up onto the upper. They might be more suited to the transitional autumn or spring when good weather isn’t guaranteed, but the bad weather isn’t terrible either. 

What sets these apart is their style. The contoured chocolate brown rubber is courtesy of Japanese manufacturer Moonstar, and it melds so effortlessly with the almond-hued canvas upper. Wear with some loose-fitting Earth-toned trousers, a white oxford shirt, and a grandiose puffer jacket for the ultimate city style.