This year’s theme: seriously functional winter footwear and apparel with standout city styling. We’re talking luxurious down, beautiful waterproof leathers, stylish boiled wools, and cozy faux fur linings—all made to handle real winter weather. So whether you’re slipping out on a Sunday morning coffee run or hustling to work in the slush, these styles deliver that elusive blend of toughness and sophistication demanded by the winter urbanite.
Merrell Captiva Buckle-Up Waterproof
Merrell’s Captiva Buckle-Up boots are some of the priciest kicks on this list at a steep $220. At that cost, a girl should expect some serious technical features. What it delivers: gorgeous waterproof full grain leather, comfy midsole for all-day wear, and a nice breathable mesh lining. As with a number of boots on this list, there is no insulation in the Captiva, so factor in thicker socks when making a decision on size. I love the nice tall height of the upper, but ladies with larger calves should be aware of the 15” circumference. (I have very slim calves and these boots barely zip up with over a pair of jeans.)
Merrell Eva Puffy Redux
The Captiva is paired here with Merrell’s Eva Puffy Redux ($159). Tough enough for the mountains, this cute puffy is also well-suited for a casual weekend in town. The polyester fabric is DWR coated to resist moisture and staining, and the 200 grams of synthetic insulation will keep your core toasty. I especially love the conspicuously oversized collar and hood.
Sperry Winter Cove Boot
This is Sperry’s very first winter boot and I am excited to include it on the list of my favorites this year. The Winter Cove Boot ($130) is a true all-around winter boot featuring all the good stuff: breathable waterproof liner, slip resistant rubber outsole, fleece ankle liner, and faux fur above the ankle to keep the chill out. If your winter morning route has you wading through snow or slush, this is one of the best “commuter” boots in the lineup.
Columbia Hexbreaker Long Down Jacket
There are so many things to love about the Columbia’s Hexbreaker Long Down Jacket ($290). For starters, it’s an affordable option in comparison to its competitors from Patagonia or The North Face. The 600-fill down is a formidable answer to the iciest Minneapolis winter days, and the knee length cut provides ample coverage from the elements. A removable storm hood and Columbia’s trademark Omni-Heat reflective lining add an extra heaping of warmth.
Tecnica Moon Boot W.E. Monaco Felt
These are the toughest Moon Boots I’ve reviewed to date. In the W.E. Monaco Felt’s ($160), Tecnica has amped up the iconic silhouette with a removable waterproof felt liner for insulation, and a rugged nylon upper. This is my choice for the years’ best aprés ski boot because of the distinctive blend of coziness, hardiness, and style. Pair with insulated leggings and a hot toddy. ($160 at tecnicausa.com)
Merrell Odda Boiled Wool Swacket
The Moon Boot is shown here with Merrell’s elegant Odda Boiled Wool Swacket ($189). Things I love about the Swacket: flattering feminine fit, high collar, sophisticated boiled wool composition, and to-the-thigh length. Although the arms are lined, the body is not, making this a better choice for milder winter days.
Timberland Stratham Heights Tall Zip WP Boot
My favorite thing about Timberland boots (besides their consistently impeccable style) is the company’s eco-friendly conscience. The sophisticated Stratham Heights ($200) not only feature full-grain waterproof leather for soggy winter days, they also boast a recycled rubber lug outsole and a mesh lining made of recycled plastic bottles. Even more impressive: the leather is from a tannery noted for its low-impact water, energy, and waste management practices. Note: the heel height is a steep 3.25 inches, so watch it on the ice, ladies.
Ibex Chamonix Coat
The Ibex Chamonix Coat is on the top of my list for Santa this year. At $525, this coat isn’t exactly “affordable,” but it’s so versatile that it can function as an everyday go-to coat. I have a particular appreciation for a piece that can transition so effortlessly from work-wear to weekend. Its refined, timeless features (elegant boiled merino wool, fully lined with 100-percent silk) are simple and unpretentious. If you’re curious, it’s also identical to the Ibex Lexi Coat, below, but with a knee-length cut.
Timberland Stratham Heights Tall Lace WP Boot
The Stratham Heights Tall Lace is a variation of the Stratham Heights Tall Zip boot above. It retains all the same impressive earth-friendly details (recycled materials and leather tanned in an environmentally sound facility) with the added style of full laces. Not to worry, there is a full side-zip to spare you the tedium of lacing and unlacing. These boots win the biggest-dent-in-your-wallet prize ($240), but your conscience may be soothed by the knowledge that these environmentally responsible boots are impeccably constructed from top-shelf materials.
Bogs Alexandria Lace Boot
I’m not entirely sure how Bogs has escaped this list in the past, but I’m so happy to include them this year that they’re on here twice. This is the Alexandria Lace Boot ($130), featuring a lace-up, waterproof leather upper and “slip resistant” rubber outsole. I’m especially loving the modern ankle-length style and cushy Ortho-lite footbed. These cuties are perfectly capable of (carefully) splashing through shallow, slushy sidewalk puddles.
Patagonia Better Sweater Icelandic Coat
Confession: I am a self-diagnosed Better Sweater junkie (I own three styles and wear them on a near-daily basis). Patagonia’s Better Sweater is a cozy polyester marbled fleece reminiscent of boiled wool. Here, it is dressed up with pretty patterned details and retro-style faux horn toggle buttons. The fuzzy fleece lining is super cozy, but the warmth rating is definitely keyed to milder winter days. The Better Sweater Icelandic Fleece Coat retails for $179.
Columbia Minx Shorty Omni-Heat
The sweet Minx Shorty Omni-Heat ($90) boots by Columbia top this list as the most affordable at only $90. These are great crossover boots, as they fit as comfortably in the snowy urban streets as they do in the ski lodge. Don’t let the cute-as-a-button looks fool you: the Minx Shorty has more winter features than any of the other boots in the lineup. A waterproof membrane, 200 grams of insulation, Omni-Heat reflective lining, and a functional faux fur collar combine to provide full protection from wind, snow, water, and freezing temps. Not too bad for the least expensive boot on this year’s list.
Horny Toad Keyboard Skirt
Shown here with the Minx Shorty boot is Horny Toad’s winter-friendly Keyboard Skirt ($72). Pair it with some cozy leggings and you’ve just cinched your new winter weekend uniform. Hidden bonus: there is a little pocket on the inside of the fold-over waistband.
Teva De La Vina
Teva’s De La Vina boot ($180) isn’t new for this winter, but I had to include it on this list because of its ability to transition seamlessly from slushy sidewalks to the office. This is a great everyday winter boot whose fully waterproof leather upper is functional and beautiful. A nice grippy rubber tread helps thwart slipping on icy sidewalks, and an inner side zip provides easy on and off. This boot is not insulated, so its ideal climate is mild and wet (hello Seattleites).
Ibex Lexi Coat
Just because we live in a city, we shouldn’t have to compromise warmth for formality. This is why I love the dreamy Ibex Lexi Coat ($475), which tops my list as the ultimate winter city coat. The luxurious (and naturally warm) boiled merino is fully lined with plush silk, making it a smart choice for professional women in cold climates. I appreciate the thoughtful details, like the close-fitting silhouette, high collar, and cozy lined zip pockets.
Sorel Toronto Boot
Waterproof oiled suede, molded EVA footbed, klutz-friendly rubber wedge heel: these are the makings of a 5-star winter city boot. I have to admit, I was a little skeptical about the weather-resistance of the Toronto (suede is not exactly renowned for its durability), but after a thorough dunking, the suede is definitely still flawless. Although not insulated, these pretty boots are lined with an incredibly soft knit lining. The rubber and foam heel also provide a nicely cushioned landing for ladies who are on their feet all day. $180.
Horny Toad Marlevelous Pullover
I’ve paired the Toronto Boot here with Horny Toad’s Marlevelous Pullover sweater ($139). I’ve had the opportunity to run around town in this sweater all month, and it now lovingly enjoys a spot on my list of favorite things. I love the cute little drop tail that covers a legging-clad bum, and the super soft, marled merino wool. Bonus details: the adorable pleated back and patched elbows. Extra bonus detail: it’s machine washable. And yes, the headband is back. Skida ($20 – $36).
L.L. Bean Signature Waxed Canvas Maine Hunting Shoe
Pair these boots with some warm wooly socks and you’ve got a killer wet-weather winter boot. The Maine Hunting Shoe ($179) should stand up to those notoriously nasty New England winter days. The tall, waxed canvas shaft performs the double function of adding some much-appreciated femininity to Bean’s iconic style, and keeping your calf completely dry (the boots have a full gusset all the way to the top of the boot). Aggressive chain-tread soles prevent slipping, and a steel shank may help stave off foot fatigue for all-day wear. One chore: it can be a bit of a hassle to get in and out of the 14-eyelet laces. The benefit: The laces allow a fully customizable fit in the calf, and you can really cinch them down to keep out the wind and slush.
L.L. Bean Signature Hooded Quilted Vest
I’ve paired the Hunting Shoe with the super cool and versatile L.L. Bean Signature Hooded Quilted Vest (a steal at only $99). I’ve been wearing this vest nearly every day this fall, and if I didn’t have to send the sample back I’d likely wear it through all my winter weekends as well. The down fill provides just enough insulation for milder days, and I love the thoughtfully designed slim fit and contrast lining.
Bogs Summit Knit WP Boots
This clever little Summit Knit boot ($104) hides quite a bit of brawn behind that sweet facade. Bogs describes in as a “cozy cabin boot,” and I couldn’t agree more (although I think its a lot more functional than that description would suggest). Just a sampling of its notable features: insulated for comfort down to 14 degrees, cozy plush lining, machine washable, 100% waterproof, and a tough rubber outsole. That’s one heck of a “cabin boot.” Note: calf circumference is a slender 14 inches.
SmartWool Hesperus Full Zip Sweater
Speaking of cabins, the SmartWool Hesperus Full Zip sweater ($240) makes me want to sit around a wood stove sipping warm beverages all day. At the same time, the pretty cable knit merino is just as functional as winter office attire when paired with some herringbone trousers and heels. My favorite feature of the Hesperus: the smart and invisible magnetic closures over the zipper. I received a bunch of compliments on this sweater when I wore it on a traveling day this fall. Here, the Hesperus is shown with a SmartWool slouch hat.