These Versatile, Comfy Timberland Boots Are on Sale

Anyone who knows me will tell you that I take a lot of pride in packing perfectly for a trip, and my recent European holiday proved no different. For a jam-packed adventure that included exploring the stunning Alps of Austria and Germany in peak winter, I strategically packed a mix of interchangeable separates, plus two winter coats. I also settled on bringing only two pairs of shoes, which included my trusty over-the-knee riding boots and a rugged pair of waterproof Timberland Everleigh Chelsea Boots that I hoped would keep me comfy, cute, and dry. Admittedly, I rolled the dice on bringing the Timberland boots — I didn’t have time to test drive them before boarding the plane, so I tossed them in my bag and hoped for the best. 

Timberland Everleigh Chelsea Boot

The adventure began as soon as I checked into the Das Edelweiss Salzburg Mountain Resort, where the first activity of the evening was a traditional torchlight hike in the snow. This charming welcome walk was an idyllic way for guests to get acquainted with the staff as well as the storybook-like snow village where the recently renovated, five-star property (which is quite literally built into a glacial mountain) is situated; however, the sleet and snow on the ground proved a bit treacherous for anyone not accustomed to those conditions. My friend almost instantly slipped and lost his footing in his dressy leather boots early into the hike; meanwhile, I was delighted to find my brand new Timberlands kept me solid and stable with no problem.

As my travels continued throughout picturesque Bavaria, Germany and back again in Austria, my durable Chelsea boots served as my saving grace time and time again. For starters, they proved to be incredibly comfy and also quite stylish. They boast a sturdy rubber lug outsole, an OrthoLite Impressions memory foam footbed, and an EVA midsole, which work together to make walking, standing, and treading through snowy conditions easy and actually enjoyable. Best of all, these winter boots are constructed of a buttery smooth, luxe-looking upper made of waterproof premium leather that impressively wicks away any trace of rain, ice, or snow. As soon as I realized I would never have to worry about ruining my beautiful boots during outdoor excursions, I felt a lot more relaxed about frolicking in my snowy surroundings. 

Timberland Everleigh Chelsea Boot

Perhaps my favorite feature of these ultra-functional boots is how downright attractive and on-trend they are. Unlike other typical winter boots, they pack major style points and look great with casual and dressy outfits alike. Frequent fliers know how hard it is to find one shoe that delivers on both, so I relished the fact that I could easily wear these from day to night without a footwear swap. Throughout my journey, I sauntered through the glittering Christmas markets in Munich, dined at the world-famous elegant Garden Restaurant at the famed Hotel Bayerischer Hof, and ascended the strikingly serene mountain tops of Berchtesgaden with ease — pairing these versatile boots with skirts, fur vests, designer dresses, and more.

By the time I reached my final destination, the exquisite Stanglwirt Bio Hotel, a truly impeccable wellness spa oasis and five-star resort with a long list of famous fans around the world, I was eager to soak up my last few winter wonderland days right away. As soon as I settled into my cozy suite, I once again pulled on my reliable Timberland boots and toured the on-property organic farm, explored the awe-inspiring rock saunas and pools, visited the resident Lipizzaner horses, and hiked along the snowy grounds leading to the mountain chalet as soon as I arrived. 

With each step, I felt solidly supported and dare I say, motivated to keep moving about and exploring — especially since the sprawling, sustainable hotel was bursting with historical charm, family roots, and a rare warm authenticity. Stanglwirt quickly earned a top-tier spot in my traveler’s heart; I would visit time and time again if I could. 

Looking back, my holiday escape was everything I could have ever asked for and more — and much like the epic experiences I enjoyed, these brilliant boots did not disappoint. 

If you’re on the hunt for a reliable pair of waterproof boots this winter, keep scrolling for more options below. 

More Comfy Boots to Shop: 

Sorel Explorer Joan Waterproof Boots

Dream Pairs Waterproof Snow Boots

Blondo Waterproof Dyme Ankle Boots

Naturalizer Darry Ankle Boots

Dream Pairs Chelsea Chunky Boots 

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