I’ve scoured the top outdoor brands to find this season’s very best in style and performance. If you’re looking for warmth, durability, and panache all rolled into one, check out my top 13 picks below.
L.L.Bean Deerfield Boots Tall
L.L.Bean’s classic Deerfield Boot is more of a fall boot (there is no insulation), although the beautiful leather upper is water-resistant for slightly damp days. The substantial rubber outsole can handle slick sidewalks, and the comfortable insole provides comfort for all-day wear. I love the Deerfield boot not only for its performance and style, but also for the company behind it (as a native Mainer, I have Bean in my blood). L.L.Bean always delivers dependable construction and quality materials, and their customer service is famously one of the best in the outdoor industry. $210.
I’ve paired the Deerfield boots with the versatile, super comfy Ariana Dress from Icebreaker. Made of 100-percent merino wool, this dress is naturally warm, odor-resistant and quick-drying (hello, dream travel dress). Paired with some insulated leggings and a warm scarf, this is also an ideal winter dress. The collar can be buttoned up for a cowl neck, or unbuttoned for a flattering open neckline. $120.
Merrell Decora Prelude
The Decora Prelude provides an adorable defense against frigid weather. Don’t let the furry cuff fool you: this boot is loaded with performance features. For starters, the waterproof-breathable upper provides a double defense against wet weather and sweaty feet. The 12.5-inch shaft covers up to mid-calf, and the cuff is snug enough to completely stave off freezing air or snow. The lugs on the outsole are aggressive to prevent slipping, and the midsole is noticeably supportive and comfortable. $200.
The Decora Prelude is shown here with Sierra Designs Dridown Capiz Skirt in cranberry. I love the flattering mini-skirt style. (I find most down skirts to be a bit frumpy, but not this one.) The hydrophobic, 600-fill down Capiz skirt paired with some warm leggings is my favorite après ski look of the season. $99.
Timberland Earthkeepers Savin Hill Mid
I am super excited to get Timberland in the lineup this year. I wanted to review about 30 of their boots, but I settled on the Earthkeepers Savin Hill Mid boot for its timeless, year-round style and eco-conscious construction. The cute printed liner is made from 100-percent recycled plastic bottles, and the outsole is made with 15-percent recycled rubber. A convenient medial zipper provides easy in-and-out. Throw them on with a pair of cozy leggings for a smart, eco-friendly après look. $180.
I’ve paired the Savin Hill Mid with The North Face’s Jacquardigan Sweater. I love the long silhouette, which covers your assets when worn with leggings. $99.
Timberland 14” Premium Waterproof Boot
Timberland’s 14” Premium Waterproof Boot is the most bad-ass boot I’ve ever reviewed. Timberland has ingeniously sexed up its classic Maine-woodsman-style boot with a 14-inch shaft. But the boot has retained its traditional hard-working features, like the waterproof full-grain leather upper, rust-proof hardware, brawny rubber lugs, and lace-up custom fit. Timberland will even let you customize the leather color, hardware, and stitching for your own unique look. Warning: this boot will require some breaking in. $200.
The 14” Waterproof Boot is shown here with Mountain Hardwear’s new Stretchstone Flannel Hooded Shirt. It looks like a cute flannel, but it behaves like a performance mid-layer. The fabric is stretchy for active sports like climbing, and the loose hood tucks nicely under a helmet. I’m loving the versatility of this piece. $85.
Keen Hoo Doo II
Keen always delivers with classic crossover winter boots. The Hoo Doo II is an update of one of my favorite winter styles, and is loaded with technical features like a waterproof nubuck upper, moisture-wicking lining, aggressive non-slip lugs, 200 grams of insulation, and a no-nonsense toe bumper. This boot transitions seamlessly from a long winter walk (a shank keeps you stable on uneven trails) to drinks in town without missing a beat. Bonus points: this is one of the most affordable choices in the lineup. $150.
The Hoo Doo II is paired here with the Isis Piazza Sweater and Isis’ fun Sofia Hat. I love the sweater’s feminine fit and super soft cotton/nylon/merino construction. Stand-out features are the thumb loops and cool exposed silky liner at the collar. The Piazza is also a great layering piece for frigid winter days. Piazza Sweater, $99; Sofia Hat, $32.
Moon Boot Monaco
I love it when a boot that looks like it’s only built for style surprises me with serious performance features. The Monaco combines the classic Moon Boot silhouette with a faux fur cuff to keep the chill out, and a cozy, removable felt lining for convenient fast drying. The nylon upper is super durable, and the outsole is aggressive enough to handle slick, slippery sidewalks. The Monaco is where warm, dry feet meet sexy, fun style. $160.
I’ve paired the Monaco with Dale of Norway’s super opulent Hemsedal zip cardigan. I love the high neck and fitted ribbed hem. This piece is pretty pricey (around $270), but its premium Norwegian wool and impeccable construction justify the steep price tag. Although it’s fitted enough to wear as a mid-layer, I’m a sucker for the beautiful retro style and like to wear it all by itself. $270.
Helly Hansen Solli Tall Boot
The waterproof leather and ultra-grippy outsole make Helly Hansen’s Solli a serious winter boot. Combine these features with a beautiful tall shaft and stylish lace-up fit and voila: Helly Hansen has managed to make one of the most handsome, hard-working winter boots I could find. Slip them on after a ski day, or pair them with jeans on a snowy Saturday; the versatility of the Solli makes the steep price tag worth it. $220.
The Solli is shown with one of my very favorite new pieces from Patagonia, the Fiona Parka. The 800-fill goose down is super warm and compressible, and the slim, feminine fit is incredibly flattering. I also appreciate the slightly flared hem for optimal movement. The Fiona has a windproof, water-resistant finish in case you get caught in a squall. I also love that the polyester shell is made from recycled soda bottles. $299.
The North Face Snowtropolis Lace Boot
Sure, the Snowtropolis Lace Boot is pretty, but would TNF make a boot that wasn’t loaded with technical features? With a waterproof, full-grain leather and suede upper, 200 grams of insulation, side zipper for easy on-and-off, moisture-wicking lining, temperature-sensitive lugs for grip, and comfy compression-molded midsole, this is a truly superior winter boot. The cute knit cuff can be folded down (as shown here) or up for a taller shaft height. $220.
I love insulated vests, so I was psyched to include TNF’s Thermoball Vest in the lineup, shown here with the Snowtropolis boot. There are virtually no limits to the usefulness of this super-lightweight little layering piece. This is a perfect layer for winter hiking or AT skiing, and pretty enough to simply wear around town on a cool day. It is also feather-light, which makes it an ideal piece for backpacking trips (it can stow itself in its own pocket), and the incredibly warm Thermoball insulation is the equivalent of 600-fill down. $149.
Kamik Jennifer Boot
The best thing about the Kamik Jennifer Boot is its practical year-round use. If you live in a wet region, chances are your wardrobe calls for a proper rain boot no matter what time of year it is. I love the Jennifer Boot for its classic Wellie style and protective 16″ shaft (on my 5’5″ frame that’s nearly to the top of the calf). The chunky outsole provides good grip for slippery footing. This boot is 100-percent recyclable and comes in a range of fun colors. $64.99.
The Jennifer Boot is shown here with the beautiful Icebreaker Coronet Long Sleeve Half Zip sweater, made from super high quality, fine-gauge merino wool. I love the heavier weight, which is substantial enough for frosty après ski excursions. The feminine fit is ideal for bunch-free layering, and flattering enough to wear on its own. The thumb loops and contrasting asymmetrical collar add a touch of sporty style. Although Icebreaker’s pieces can be pricier than other brands, the wool is some of the finest out there and I’m a huge supporter of their ethical, earth-friendly, animal-friendly philosophy. Check out their story here. $190.
Ahnu’s Larkspur is the perfect urban boot for moderate winter weather. The suede upper is waterproof, and the moisture-wicking mesh lining provides some nice interior climate control. Although not insulated, this is a great boot for cruising around the city on mild, wet days. Bonus: The side zip provides quick on-and-off. $160.
The Larkspur is paired here with Sierra Designs’ DriDown Capiz Jacket. The jacket has a very flattering fitted silhouette with stretchy nylon/spandex side panels for greater flexibility. The Capiz is filled with 65 grams of DriDown, Sierra Designs’ proprietary hydrophobic down designed to dry faster and stay loftier than regular down. $199.
Columbia Bugaboot Original Chukka Omni-Heat
Columbia’s Bugaboot Original Chukka is a welcome antidote for tired feet that have been stuffed in ski boots all day. They’re like cozy slippers that can handle cold, wet winter days. The waterproof full-grain leather upper combined with 100 grams of insulation and Columbia’s signature Omni-Heat reflective lining will keep your feet warm and dry on moderate winter days. By virtue of the fact that this is an ankle-height boot, you won’t want to go plunging into deep snow drifts, but I like that the cuff can fold up for a snugger fit around the ankle. $130.
The Bugaboot Chukka is shown here with Dale of Norway’s 100% Norwegian wool Nansen Feminine sweater. If you feel like a little splurge, it doesn’t get more luxurious than Dale’s classic ski sweaters.
Patagonia Maha Slouch
The Maha Slouch’s slip-on moccasin style is perfect for après ski comfort. This boot looks more precious than it is: the suede leather upper is actually waterproof, and the boot is lined with breathable polyester mesh for moisture-control. There isn’t a thick, burly outsole, but the rubber sole is textured for grip on moderately slick ground—I actually love the slipper-like silhouette. $160.
The Maha Slouch is shown here with The North Face’s sophisticated and cozy Caroluna Jacket. I love the longer, feminine-tailored waistline and button-up collar. The exterior is a casual, quilted cotton/polyester, and the inside is a luxurious, soft fleece. Perks include the multi-seasonal wearability and easy-to-care-for fabric. $120.
Sorel Slimpack Riding Tall Boot
I’m a sucker for all things equestrian, so naturally I love Sorel’s Slimpack Riding Tall Boot. The full-grain leather upper is waterproof to the top of the shaft—the only fully waterproof leather boot in the lineup. The Slimpack also boasts a comfy, molded-EVA footbed, microfleece lining with 100 grams of insulation, and a grippy rubber herringbone outsole. An added bonus is the adjustable shaft to accommodate different calf sizes. Double bonus: it’s stylish enough to wear with jeans even when nasty weather is not in the forecast. $210.
Here, I’ve paired the Slimpack Riding boot with one of the sweetest new styles from Icebreaker: the Bliss Wrap. This cozy piece is pricey at nearly $140, but you get a lot of bang for your buck. The lightweight 100-percent merino wool is naturally odor resistant, warm, and breathable, and it can be worn any time of the year. I also love the versatility of this wrap: it can be styled in three different ways. $140.