Snowflakes, ice skating and curling up by the fire are some of the best parts of winter, but sleet, slick sidewalks and freezing temps definitely are not. It’s the latter that make the cold weather season a major bummer, especially in the style department. Winter essentials no doubt get the job done in terms of keeping you cozy, but they have a habit of being bulky, clunky and downright dowdy. But not hiking or winter boots. They’re rugged, badass and will totally show cold weather who’s boss. Now let us show you how you can earn best-dressed status in those steppers at the office, after hours and on the weekends.

How to Wear Hiking Boots at the Office


Polished pumps are a workweek given, but once winter rolls around, they just can’t hack it on your morning commute. Hiking boots won’t just kill it during those pre-office hours, but they’ll put an unexpected twist on your nine-to-five getup too. Pair them up with printed pants that sit perfectly above the ankle to show off your bold footwear and a lacy, high-neck top for a soft, feminine touch. To highlight your sartorial know-how, accessories should be eye-catching and modern, like a felt and leather-trimmed backpack, colorful, shimmery drop earrings and a swipe of dark berry lipstick.

Woolrich Yankee Work Boot ($325) + Zara Trousers With Zips ($40), & Other Stories Floral Lace Top ($125), J.Crew Campbell Blazer ($248), Sorrelli Swarovski Crystal Drop Earrings ($150), Zac Posen Eartha Leather-Trimmed Felt Backpack ($198), Forbidden Lipstick in Fortune Teller ($23)

How to Wear Hiking Boots on a Night Out


Let’s be real — strappy sandals and stilettos just aren’t going to fly when it’s cold and wet outside. Make your night-out look feel fit for the season by topping off a sequin-studded skirt with a turtleneck and subtle polka dot tights. Worn with those rugged kicks, they’ll be racking up style points left and right, because what else could make a winter essential look so fab? As a finishing touch, tack on a few marble-inspired baubles for an element of sophistication and a fuzzy faux fur coat that screams cozy-glam.

Woolrich Yankee Work Boot ($325) + & Other Stories Cashmere Turtleneck Sweater ($195), H&M Skirt With Sequined Embroidery ($40), Zara Swiss Dot Tights ($16), Topshop Faux Fur Contrast Collar Patterned Coat ($170), Whistles Howlite Ball Ring ($38), Noonday Collection Metallic Teardrop Earrings ($48), J.Crew Envelope Clutch ($128)

How to Wear Hiking Boots on the Weekend


Jeans and a sweater just feel *so right* with a pair of hiking boots, but skip the skinnies and cashmere pullover for something with a little more pizazz. A bright chunky knit will kick the winter blues to the curb, while boyfriend jeans are all about keepin’ it real — comfy, that is. Swap out your go-to layering tee for a floral blouse to add a note of polish to the off-the-clock ensemble and complete the look with a warm blanket scarf and roomy satchel bag.

Woolrich Yankee Work Boot ($325) + Rag & Bone Marilyn High-Rise Slim Boyfriend Jeans ($138), Topshop Premium Bright Shaggy Cardigan ($160), Warehouse Long Sleeve Wrap Front Blouse ($71), Seaworthy Lanata Necklace ($142), Kelsi Dagger Heritage Clutch ($98), Madewell Checkmate Scarf ($60)

How would you give a pair of rugged boots new life? Show us how you ace your winter style game by tagging us in your #OOTDs on Instagram.