Holiday gifting season is almost here, and Timberland’s latest gear collection proves that practical can still be flex-worthy. From modern day takes on boots that helped define ‘90s hip-hop culture, to premium puffers and refreshingly durable (and stylish) boat shoes, here are Timberland essentials for the ones you love.

Price: $130

Traditional boat shoes are a versatile style choice, but they often lack adequate comfort and durability. Timberland provides the best of all three worlds with the Stone Street Platform Boat Shoe. Its OrthoLite® Impressions memory foam footbed offers plenty of cushion for on-the-go feet. They also pair well with baggy blue or black jeans, and the platform component may be the perfect gift for the short queen in your life who just wants to be able to see at concerts.

Price: $210

The OG yellow boots look and feel like hip-hop. In the ‘90s, rappers adopted “Timbs” as a streetwear staple that has remained iconic through the decades. Of course, the modern-day iteration boasts a wide array of colorways (personally, we like this one), as well as Timberland’s latest technology. Its 400 grams of PrimaLoft® insulation keeps feet extra warm and prevents water penetration. Gift a pair to the hip hop aficionado in your life—or to someone who regularly contends with colder conditions.

Price: $170

We all have that leopard print-obsessed person in our lives. Needless to say, the Stone Street Platform Hiker is the boot for them—or for anyone else that wants to stand out in the crowd. The statement pair doesn’t sacrifice function, which means it’s an ideal selection for casual nights out and long walks through the city. Best of all, it’s environmentally friendly, as 10% of the rubber in the outsole is sourced from farms committed to regenerative agriculture, so wearers can look good and feel good about their choice to wear the hiker boot.

Price: $110

Nothing sabotages a fly fit like a bad outerwear choice. On the contrary, Timberland’s Welch Mountain Durable Water-Repellent Puffer Vest enhances any outfit. The puffer offers a layered look, meaning that it can be worn over a cozy turtleneck sweater or a colorful flannel (more on that later). Its warm, insulated liner makes it the perfect companion piece for those who get extra chilly in the wintry months and need to bundle up.

Price: $210

There’s a common give and take with winter boots. They are often warm, but also clunky; stylish yet heavy. The Timberland 25 6-Inch Waterproof Boot bucks the trend. This modern spin on a classic pair of Timbs offers familiar craftsmanship (rugged, supportive, durable) with 25% less weight, thanks in large part to the TimberCush™ comfort system. Athletes need to be light on their feet, just like many of us prefer that our feet feel light. Score these shoes for someone who’s always on the move.

Price: $80

Remember that Timberland puffer vest from earlier? This hoodie may be the ideal base layer for it. The soft, cotton-polyester material blend is built for city strolling, hitting the gym and lounging around the house. You know, for that friend who occasionally wants to pop out and show ‘em. The beauty of the understated, laid back design is that it complements almost everything, making it another wardrobe staple to add to the rotation.

Price: $170

The Men’s Timberland Authentics 3‑Eye Lug Handsewn Boat Shoe in rich burgundy is the quintessential hybrid of rugged and refined. Its timeless handsewn detailing and sturdy lug sole provide just the right amount of polish. It’s a must-have for the person in your life who suits up for the office five days a week and frequently goes on dates. Cuffing season, fielding season, or time-to-achieve-those-long-term relationship goals season, this boat shoe is primed for it all.

Price: $60

Nothing evokes fall quite like a well-worn flannel. Enter the Timberland Women’s Midweight Flannel Pocket Shirt. With its relaxed fit and breathable, organically grown cotton weave, the stylish long sleeve is a go-to for when the temperature dips. Wear it solo or layer it with other cold weather clothing. The flannel effortlessly bridges the gap between outdoorsy and cozy, making it a nice wardrobe addition for a friend who wants to chill when there’s a chill in the air.

Price: $190

Constructed for whatever the season holds in store, the Men’s Britton Road Warm-Lined Waterproof Boot delivers warmth, comfort, and durability in equal measure. The waterproof construction and rugged sole make it a true all-weather player, keeping feet dry from rainfall to blizzard, while the ReBOTL™ fabric lining (made with at least 50% recycled plastic) makes every step feel good, for more reasons than one. A reliable pick for the loved one who’s perpetually cold, whether they’re braving the snowy elements or padding across chilly wood floors.

Price: $85

What can we say, we like a puffer vest. So too will the gift’s recipient. This particular puffer blends neutral beige elegance with an outdoorsy practicality. It threads the always delicate needle between looking chic in the cold and staying comfortably warm. Dress it over a chunky sweater or under a shell. It’s stylish enough for city walks and durable enough for trails. Overall, it’s a smart pick for the person who seeks function and fashion.

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