Women’s Winter Boot Roundup

By Nancy Bouchard

Baby its cold outside and there is not much that’s as uncomfortable as frigid feet. While big snow days warrant thickly insulated snow boots, and freakishly warm temps lure us into wearing lightweight sneakers, hands down the most versatile winter boot is the calf-high, low-heeled leather boot. Here are three boots that will end up being your go-to footwear from October through April.

Teva De La Vina ($140)

These low-heeled leather boots are supremely comfortable—in fact they became my go-to footwear for everything from trips to Sweden, Norway, Colombia and Turkey to jaunts to mountain towns around North America. Compared to many places in the U.S., where “casual Friday” seems to have drifted to every other day of the week, in many other countries people don’t wear running shoes or flip-flops 24/7. I found the De La Vinas to be the ultimate travel boots—comfortable for 14-hour transcontinental flights, high-performance enough for impromptu day hikes, and comfortable enough for long days of traipsing through museums, parks and pubs. And there’s nothing like a pair of black (or brown) short boots to tie together any outfit—whether hiking, working or shooting pool.

The 7.5-inch shaft height  (the measurement from the middle of the arch to the top of the boot) means the boots can be worn over or under pants without looking dorky. On cold days, having pants that tuck into your boots will keep you warmer—but wider-legged pants tend to look better worn on the outside. But where the De La Vina’s win is with comfort. While the boots may feel a bit stiff across the foot out-of-the-box, after a day’s wear, the soft, supple waterproof leather stretches just enough to conform to the shape of your foot. They soften up with wear—so soon they feel more like a bespoke pair of boots that were made just for you. An even softer insert is sewn in at the Achilles and on either side of the heel—it allows the boot to flex while you walk. This season, you have the choice of a wool or leather insert. The wool adds a bit more warmth without extra weight. More comfort is assured with the soft rubber heel and sole. I’ve logged more than 100 days in my De La Vina boots—the sole provides serious comfort and support; at a lightweight 1.8 lbs per pair these sturdy boots feel more like running shoes—and have a lot more warmth, protection and style.

Timberland Whittemore Chelsea ($180)

Timberland has been making premium leather boots for more than 40 years—their tried-n-true footwear is designed with durability in mind.  “We make boots you can wear for a decade or more,” one company spokesman told me. “We base this not only on superb craftsmanship, but also classic designs that never go out of style.”

The only trouble I see with Timberland’s boots is deciding which one to wear. I own several pair of Timberland boots—well, maybe a half-dozen. Most are 5 to 10 years old—and, despite many miles in snow, slush and mud—are in primo condition.  Sure, I use a brush to clean them, and when I remember to, polish or treat the leather, but arguably they’ve gotten better with age.  The quality of the boots is unparalleled; these are not ones you’ll wear for a single season—but for years to come. While the designs are classic, they are also trans-generational, meaning that everyone from teenagers to parents to grandparents find them cool.

This year I settled on the Whittemore Chelsea. The premium full-grain leather upper won’t leak in the snow or rain. The thick rubber lug soles provide excellent traction in slick conditions—even on those days when the ice on the sidewalk is so transparent you don’t notice it until it is too late. The boots have a stitched welt—not only is the design more durable than glued welts, but they look classier. Stand out features include a leather-covered OrthoLite foam footbed. Not only do the footbeds feel like they have more cushion than many boots I’ve tested, the leather seems to breathe better than most insoles; it also doesn’t retain odor or sweat. Plus, on side-by-side tests, this footbed (aka insole) kept its cush with no discernible break down over six months of hardcore testing. This boot has a short shaft height (only 4 inches)—it works well with tights and skinny jeans. It’s a bit more dressy than many other “booties” as the heel is 1.5 inches, and the shape more “cowboy” than “snowboot.” A 4-inch medial (inside) zipper makes these boots easy to slip on or off, plus there’s a handy pull-tab stitched on the heel. These boots fit true to size—but they are low in volume. If you have a wide foot or high instep, you may want to go up a half size.

Bogs Kristina Chelsea ($150)

It’s rare that a boot this stylish and technical feels so good. This pair hits the perfect trifecta of style, waterproofness and slipper-like comfort. With no side zippers to leak (entry is made easy with elastic panels on both sides), these are some of the most waterproof boots of the season. I wore them for a week in the soggy Willamette Valley this fall, and they shed rain and puddle splashes like a duck.  The distressed full-grain leather upper is lined with an even softer leather inside so your foot slips in like Cinderella. There are elastic panels on both sides of the foot that stretch wide for easy access—we worried that they might lose their shape over time—but after 4 months of solid wear, the panels look like new. The shaft height is 6.5 inches—and the elastic inserts give them a close-fitting look—great over jeans or tights.

Bogs got its beginnings in the college town of Eugene, Oregon—originally the company catered to the surrounding farming and agricultural communities. My first experience with the brand was going with my dad to pick up some tractor parts from a local farmer. The farmer was dressed in an old Stetson, coveralls, and an amazing pair of boots. Temperatures were in the single digits—even the cows were cold.  “My wife bought me these fancy boots for Christmas,” he said proudly. “And it’s the first winter in 30 years my feet have been warm and dry.” That was in 2003, and soon after, the company started making kids shoes, and then, nearly a dozen years later, leather boots that look good on and off the farm.  While the original rubber boots are still the best for work, the leather additions to the line make the transition from farm to functional fashion.

Some waterproof boots get sweaty, but that’s not the case with the Kristina Chelsea. The insole is covered with a soft, breathable leather. Underneath is a dual-density EVA foam that provides significant cushioning. I walked around Oslo (Norway) for six hours in my boots—both on trail and sidewalk—and my feet didn’t feel sore or tired. The 1 1/8^th inch heel is high enough for fashion but low enough that active movement is never compromised. In fact, with the flexible rubber outsole, these boots are ideal for light-duty trail travel.