Anglomania http://www.out.com/sites/out.com/files/imagecache/slide-image-white/4-Asos.jpg 27848

$266,97, by ASOS, at Asos.com

The e-retailer's "Made In England" collection boasts a design quality that can rival the greatest high-fashion brands. This season, look for these pitch-black derby with electric red accents.

Explorer http://www.out.com/sites/out.com/files/imagecache/slide-image-white/3-Ugg.jpg 27847

$225, by UGG, at UggAustralia.com

The Australian shoemakers have come a long way since their signature "comfort boot," notably by diversifying their offering for men. We dig those two-tone hiker boots, which can be worn as comfortably on the adventure trail as on the urban tarmac.

Chelsea http://www.out.com/sites/out.com/files/imagecache/slide-image-white/2-Cabral.jpg 27846

$615, by Armando Cabral, at MrPorter.com

Model-turned-designer Armando Cabral treats us with some stunning chelsea boots, made with high-shine leather and contrasting aubergine stretch sides. Our luxury pick of the season.

Navy http://www.out.com/sites/out.com/files/imagecache/slide-image-white/1-Cole.jpg 27845

$228, by Cole Haan, at ColeHaan.com

Blue being the obsession of fashion designers this winter, it's time to emulate the runway look for less with Cole Haan's storm-proof chukka. If you're not into blue, don't worry: They're available in five other colors.

Patchwork http://www.out.com/sites/out.com/files/imagecache/slide-image-white/5-Thorocraft_0.jpg 27849

$300, by Thorocraft, at DJPremium.com

Sure, there's a lot going on here with the leopard-print pony skin, waterproof leather, and rubber soles, but we wouldn't expect any less from the Californian shoemakers who dazzled us all summer with their floral derbys and punch-holed brogues. Admit it, it's a nice upgrade from your Sperry's, isn't it?

$266,97, by ASOS, at Asos.com

The e-retailer's "Made In England" collection boasts a design quality that can rival the greatest high-fashion brands. This season, look for these pitch-black derby with electric red accents.