Head South For The Big Smoke—The Big Smoke Miami

Cigar Aficionado

Wellies, Wellington boots, muck boots, gum boots, top boots—whatever the name, they are the natty, pinched-ankle, high-stance rubber footwear that look so good they'll make you obey your mother and wear your galoshes on a muddy day. Naturally, you credit anything so stylishly utilitarian to the Brits and their knack for adapting military gear as everyday wear.

But that would be to ignore the Germans, French and Americans.

Yes, Wellies are named for the first Duke of Wellington, who apparently discovered Hessians-high-peaked leather riding boots that hugged the ankle, tapered up the calf and covered the front of the knee—while thrashing Napoleon around 1815. Returning to London, he had the style modified in an order to his cobbler: cut them below the knee, lose the tassels, lower the heels and loosen the calves. Despite his military genius, Wellington ("the Beau" to fellow officers) preferred civilian clothes to uniform. And, without the riding heels, his boots weren't really military issue anymore. But you could socialize in them, and they did go well with the Regency vogue for pantaloons instead of knee britches. Wellington's war-hero status and the adoption of the look by his fashion-plate friend Beau Brummell drove a trend. The field marshal who had once bragged that his troops were the "best shod in Europe" could now claim the same for himself in St. James's.

Wellingtons emigrated to the United States, where they inspired cowboy boots and then had a substantive change. Charles Goodyear's development of vulcanized rubber allowed the boots to morph into rainwear. American entrepreneurs brought the advancement to Europe, where they made rubber boots, first in France in 1853 as Aigle (www.aigleboots.com), then in Scotland in 1856 as the North British Rubber Co., now Hunter Boots (www.hunter-boots.com).

The look is so timeless and overarching (wear them over dungarees one day and suit pants the next) that preppies inevitably made it a style statement of their own. Nevertheless, the best makers maintain the conceit that these boots are made for wading in field and stream and not walking through Starbucks. Manly color choices have gravitated to black and the olive seen here in Barbour's "country boot" (www.barbour.com), although even pink can be had. Of course, neoprene and latex have joined vulcanized rubber as materials of choice, although Orvis (www.orvis.com) still honors the Duke with a leather pair.