Nothing beats the effectiveness of shearling at keeping cold out and heat in, but that doesn’t mean you have to walk around in perpetual après-ski mode. Look for insulating linings where you’d least expect them: These boots from Ugg Australia seem like just a cool leather moto style, but they hide a thick, wooly insole, like the brand’s more casual classics.
To buy: $200, uggaustralia.com.
Over the Knee
Like armor for winter warriors, over-the-knee boots keep your legs toasty and wind-proof. Flat-soled styles offer a more laid-back look than sexier, high-heeled versions. Pair them with a midi skirt or pull them on over your favorite skinny jeans or leggings.
To buy: $100, chineselaundry.com.
Skip the unlined rubber rain boots if you’re preparing to struggle through sleet and slush—your feet will freeze in seconds. Opt instead for a cozier, water-repellent pair. A nylon upper, like this style, works well to keep out the wet. We also love the buckle and snap closures, which mean they can be worn cuffed or closed, depending on your outfit.
To buy: $269, mattbernson.com.
Stilettos? In the snow? While this pair may not get you through a blizzard, they’re great for frosty city streets. A rubber lug sole offers enough traction to navigate icy stretches of sidewalk, while the black leather and sleek styling won’t look out of place with a skirt or trousers for work.
To buy: $149, zappos.com.