Among the many problems winter presents, there is the problem of footwear. If you live in a snowy climate, or even in a temperate zone where the coldest season brings icy rain, the dilemma is familiar: Do you trudge through slush in expensive, stylish boots, watching helplessly as the water warps and wrinkles your investment (and cringing as the damp seeps through to your toes)? Do you mar a professional look with dowdy, practical boots in cheap synthetic fabrics or inferior, waterproof "leather"? Do you change upon arrival at work, lugging a more fashionable pair in your bag? Do you park a single pair of uninspired black flats beneath your desk? Or pad around in stocking feet, as though the office were your bedroom? The options seem foppish and insouciant on the one hand, cumbersome and high-maintenance on the other. Yet each year without fail, style writers anoint the winter's impractical, must-have cult boot (riding boots, cowboy boots, Fryes, Uggs), leaving the rest of us with a question that nags like wet socks during a workday: Is there a way to be dry, warm, and fashionable?
This question has vexed me my entire adult life. Like many women who grew up in the 1980s, I have pleasant memories of setting my moon boots out to dry in front of my grade school's "coatroom" door. Pulling those clodhoppers off and on, sitting in the classroom in socks: All this injected some much needed excitement into the monotony of a schoolchild's day. But when I began to shuttle back and forth between home and work, my choice of winter footwear became an absorbing consideration. During the several winters I was employed at a highbrow literary magazine—a place where the word "style" applied only to writing—I tramped to the office in Adidas sneakers, inwardly shamed by my frumpiness. Finally, I blew a paycheck on an outrageously pricey pair of sleek, black, high-shafted Guccis; it was not long before the street salt corroded them beyond recognition.
There is some consolation in knowing one isn't alone in this predicament. For centuries, people have pondered how best to attire one's feet for inclement weather. Ancient Egyptians, when faced with the flooding Nile, relied on sandals with high soles of solid wood, writes Colin McDowell in his excellent study, Shoes: Fashion and Fantasy. From roughly the 14th to the 19th century, women in England and Europe wore wooden structures called pattens—a cross between platforms and clogs, these covered the shoes and were supported by iron rings—to assist them in negotiating muddy, unpaved roads. (Elizabeth Bennet must have forgotten hers when she turned down Mr. Collins' offer to see his meadow on the grounds that she did "not hav[e] shoes to encounter the remains of a white frost.") Unfortunately, pattens were not only a production to put on, they often sunk into the mire, as an exasperated Samuel Pepys complained to his diary about a walk with his wife. ("My wife ... being exceedingly troubled by a new pair of pattens, and I vexed to go slow ...") Plus, the iron rings clinked irritatingly as they hit any hard surface, making pattens the cell phones of their day—notices posted on church doors often requested that women remove them before entering.
It wasn't until the 19th century that boots entered the equation; before then, it was considered unseemly for women to don them, even if they were going horseback riding. Yet with the introduction of pendular, steel-cage crinolines in the 1850s—which meant that skirts now swung back and forth like a bell as a woman walked or danced, exposing her ankles—the buttoned or laced boot became a fashionable way of shielding the female leg from the curious male gaze, notes McDowell. Unfortunately, these boots were generally made from fine materials like kid leather or cashmere and didn't always hold up in rain or snow. As a Victorian guide to fashion counseled: "For those who are not very particular about their appearance, and walk little, thin boots and goloshes [sic] are the most economical, though certainly not becoming. …" Around the turn of the century, boots went out of fashion and remained unpopular until the early 1960s, when they once again became trendy, and styles such as André Courrèges' 1964 white midcalf "Space Age" boots—similar to those Lori Williams sported in Faster Pussycat, Kill! Kill!—were designed, as they are still, purely for effect.
This season, however, fashion and function are holding a rare summit: It's now possible to find boots that are stylish and durable and warm. Most major labels have offered an interpretation on two dominant styles—enormous, furry après-ski boots; or slimmer suede boots that often lace up the leg and have either a wedged 1970s-style rubber heel or a flat, moccasin-like sole. (A handful of designers, such as Christian Dior and Marc Jacobs, have issued moon boots, but this trend is right only for a woman who doesn't mind actually looking like an astronaut.) Insulated mainly with fleece, shearling, or faux fur lining, these boots will keep feet cozy even in the worst sludge. Among the most attractive are Donna Karan's basic shearling boot in beige suede ($683); Coach's Aspen-glamorous white quilted nylon boot with rabbit fur trim and wedged heel ($400); and Cole Haan's more urbane black shearling "G series" boot with a flat "nubbed rubber bottom" ($225). As for staying dry, nylon is of course waterproof, and, according to several salespeople I questioned, faux fur also stands up to precipitation. Suede is often pretreated these days, but if your boots aren't, simply coat them with protective spray, easily purchased for around $5 at your local shoe repair store, have a cobbler put rubber bottoms on any leather soles (to avoid slipping), and you're good to go.
But what if the Clydesdale-hoof look won't fly in your office? Or if you don't want to masquerade as Robin Hood of the cubicle forest? What if tucking your pants into the shafts of your retro-wedged boots, à la Chrissy on Three's Company, just feels wrong? Don't despair. A resourceful friend suggests a feasible if imperfect solution. Each winter, she purchases a classic yet inexpensive pair of slim, black, knee-high leather boots, the kind that work as well with a mini as they do with a pair of trousers, at, say, J. Crew, and wears them with heavy socks on the sloppiest, most tempestuous days, saving her designer boots for less messy weather. Yet she admits she's coming around to the more relaxed approach of her friend Andrea Linett, the creative director of Lucky, who this fall bought herself a pair of Dries Van Noten boots and plans to wear them like a mail carrier, come rain, shine, sleet, or snow, on the theory that the older they look, the more character they'll have. She may be onto something. In the end, boots, to offer a twist on the phrase popularized by Nancy Sinatra, are made for trudging.