Men’s Winter Fashion Trends and Essentials: 2021 Style Guide

We’re looking at trends differently this season. What is the secret to looking stylish as it gets colder and as we’re still in the midst of a pandemic? The answer involves selecting pieces that are practical, comfortable and will make getting dressed feel good. Shearling outerwear to keep you warm, and lug soles to keep you in step as the ground freezes over. Bright graphic knits that are not only cozy but will be a much-needed optimistic talking point for your next video call. And fleece jackets because let’s face it: We fully support any clothing that stylishly emanates a cloud hug right about now.

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The Trailblazer

After months of staying indoors, dressing for a hike (or a walk around the block) instantly feels like a breath of fresh air. Earth tones like forest green, dune, and charcoal can help to transport you to nature. Look for strong pieces like hiking boots, multi-pocketed pants and carabiner-accented accessories that are easily workable with other items you already have.

Coach Hybrid Pouch 8

Coach’s leather pouch is a perfect way to keep essentials organized in one place while stylishly clipping onto your belt or bag.

Carhartt Ripstop Relaxed Fit Double-Front Cargo Work Pant

These bad boys are made from abrasion-resistant fabric that is ideal for exploring on and off the trail.

Hoka Kaha Gore-Tex Boot

Swedish activewear brand Hoka’s hiking boots look just as good with outdoors gear or your favorite pair of jeans.

Shearling Remixed

Shearling has been the cool coat of choice for many a 70s music icon. And while it isn’t new by any means, we love to see it styled in a modern way a la Virgil Abloh for Louis Vuitton. We’re all about a shearling collar and material mix, whether it’s denim, houndstooth, leather, or wool.

Levi’s Sherpa Trucker Jacket

Levi’s clever combination of crisp denim and cozy sherpa makes for a new classic that looks good on everyone.

Sandro Woolcloth Aviator Jacket

Sandro’s aviator jacket boasts smart details including a heritage herringbone fabric, pronounced pockets, and a detachable sheepskin collar.

Mango Faux Shearling Wool Blend Jacket

Mango’s faux shearling offers a more sustainable option that’s just as warm with a reduced environmental impact.

Lug Sole Boots

2020 has made you tougher and now you just need the footwear to prove it. The great thing about a daring accessory? You don’t have to change your entire wardrobe to make them work. Leather, suede, lace up or Chelsea: lug sole boots offer an easy way to instantly add a bit of grit to your everyday ensemble.

UO Lorenzo Chunky Chelsea Boot

Urban’s suede Lorenzo boots are a low-lift way to try the lug sole trend without getting too invested.

Prada Lug-Sole Combat Boots

If there’s any shoe that you’re seeing on social this season, it’s Prada’s lace up, leather, and lug sole styles that set the bar for the tough trend.

Zara Lug Sole Leather Boots

Zara’s sleek leather Chelsea boots are just as easy to put on as they are to pull off.

Graphic Heritage Knits

Feeling like you need an article of clothing to help you stand out in monotonous meetings? Try a traditional heritage knit sweater with a modernized edge. Think: A camel-striped cardigan remixed with cool checks, or a fairisle crew knit in unexpected brighter colors. Our pick: Rowing Blazer’s iconic black sheep sweater that’s available for pre-order.

Warm & Wonderful x Rowing Blazers Men’s Sheep Sweater

The original Warm & Wonderful black sheep sweater became famous with British royalty in the late 70s, only to be relaunched exclusively with Rowing Blazers this year.

Without Walls Graphic Zip-Up Cardigan

The quintessential intarsia knit gets an update with this Without Walls mixed graphics zip-up.

Land’s End Men’s Lighthouse Fairisle Crew Sweater

An updated classic knit from Land’s End keeps you super warm while keeping a smile on the faces around you.

Fleece Jackets

We get it. It’s been a tough year and you need something other than your go-to hoodie that you feel good wearing for hours on end. Enter the fleece. It’s essentially wearing a blanket as outerwear, and that’s okay. Our tip: Stick to your true sizing and balance with a more structured pant to maintain a silhouette that says cozy and cool.

Patagonia Men’s Classic Retro-X Fleece Jacket in Natural

Environmentally  friendly outdoors brand Patagonia’s fleece is warm, windproof, and Fair Trade Certified.

Reese Cooper Sherpa Fleece in Forest

RCI’s signature style features roomy nylon pockets and elastic cording at the waist for ultimate insulation.

L.L. Bean Hi-Pile Fleece Pullover in Platinum/Navy

This ultra plush pullover from L.L. Bean is a re-creation of the same style worn by a USA team member during the historic 1990 Mount Everest Peace Climb.

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