4 Easy Outfits to Wear Anywhere This Winter (2024)

There’s no shame in purchasing fresh, new, comfortable clothes. Sure, the last two years have dramatically altered our daily dress. But every change to the norm has ultimately made men smarter shoppers. Think about it: Instead of frivolous impulse purchases or falling for the hype on too-trendy pieces, your winter wardrobe investments are more focused, allowing you to hone in on what brings you comfort, what’s necessary to combat the elements, and what garments have the versatility to be worn on repeat.

But even with the right winter clothes, it can be a challenge for any guy to figure out what to pair together for the ideal amount of comfort, without sacrificing cool style. The ideal winter ‘fit should look relaxed, effortlessly stylish, and incorporate all of your favorite comfy gear. While formal suiting and neckties are currently pushed to the back of your closet, we put together a few key winter outfit ideas that will have you covered for all cold-weather scenarios, from cozy WFH hours to weekend walks on snowy trails. You might have some of these wardrobe essentials in your closet already, which is awesome. But if you don’t, consider these high-quality duds to be worthy investments to cover all your bases this winter.

Simplify your cold-weather style and flex these easy ‘fits on Zoom or on the go.

Read more: Winter Style Trends for Men

WFH, But Polished

No man will complain about switching his uncomfortable, stiff trousers for soft and stretchy sweatpants. But at some point, the blurred lines between loungewear and workwear haven’t made separating working hours and off-hours any easier.

Even if you’re only visible from the waist up, a more polished WFH winter outfit will make your work life feel more normal (whatever that means these days), and boost your confidence to close that deal, ask for a promotion, and generally embody the vibes of a total boss.

The trick to a cool-yet-comfortable WFH flex is all in the details. An elevated sweater makes your go-to winter knit look a bit more elevated for mornings on Zoom. And while your coworkers won’t see your stylish pants by the water cooler this year, you will feel more confident and professional in a true pair of trousers. A relaxed-fit chino in a seriously soft fleece fabric basically feels like a more formal lounge pant, providing warmth and the ideal amount of roominess to work from your home office setup or your living room couch.

Another bonus to dressing up for work is the freedom it allows you to go for a walk or run some errands at any given free moment in your day, avoiding the quick scramble to get dressed in the afternoon when entering the outside world. Wearing cool sneakers indoors also helps to provide some much-needed foot support while walking on the hardwood floors in your home. And if you’re popping out for a quick moment or just want to show off your cool layering game to coworkers, top off your look with a winter vest.

Whatever you choose to wear during your 9-to-5, keep it classic, simple, and comfortable enough to make the long day a bit easier.

Below Freezing ‘Fits

When you’re dealing with harsh wintry conditions, does anyone really care what they look like? Maybe not, but that doesn’t mean you can’t buy stylish winter gear for your daily moves in frigid conditions. Start with your winter coat, the most important layer for combatting the cold. Opt for a quality down jacket that’s windproof, waterproof, insulating, and easy to care for. Yes, the price tag is hard to stomach, but well-done outerwear can take on the elements for many winters to come.

For a little extra protection, a long-sleeve tee with heat technology is ideal for extra warmth without adding unwanted bulk to your torso. For the lower half of your body, pants with innovative performance fabrication for added stretch and durability will help you to move freely and stay dry, even when you’re knee-deep in snow. And speaking of trekking through snow, tough waterproof winter boots with a lug sole for traction are another must-have for your wardrobe. To finish off your winter outfit, top-notch cold-weather accessories will ensure that you’re as cozy as possible.

Overall, sticking to a color scheme of neutrals, navy, and dark shades of green will make your winter outfit look sleek and timeless, but that’s not as important as the quality of your winter gear. If you’re strapped for cash and can only invest in a few key pieces this season, turn your attention to these options.

Below Freezing ‘Fits Essential

4 Easy Outfits to Wear Anywhere This Winter (5)

Buck Mason Down Expedition Jacket

4 Easy Outfits to Wear Anywhere This Winter (6)

Uniqlo Heat Tech Long-Sleeve T-Shirt

4 Easy Outfits to Wear Anywhere This Winter (7)

Timberland x PSNY 8" Pro Boot

4 Easy Outfits to Wear Anywhere This Winter (8)

Huckberry Beanie

Read more: Best Clothing Brands for Men

Winter Workout Warrior

With all the time you’re cooped up indoors during the winter, taking your workout outdoors provides a refreshing change of scenery. Still, it’s key that your gear is lightweight enough to level up your fitness game without hindering your performance. All you need is a few extra layering pieces for added warmth, like leggings to don under your workout shorts and a stretchy-yet-insulating puffer jacket to top off your cool graphic running tee. Simple and stylish.

Winter Workout Warrior Essentials

4 Easy Outfits to Wear Anywhere This Winter (9)

Vuori Limitless Compression Tight

Now 61% Off

4 Easy Outfits to Wear Anywhere This Winter (10)

Reigning Champ 7" Hybrid Training Short

Now 50% Off

4 Easy Outfits to Wear Anywhere This Winter (11)

Arc'teryx Cerium SL Down Hoody
Men's Health Cut & Ripped & Jacked & Swole T-Shirt

$25 at Men's Health Shop

City Sweats

Who says you can’t look stylish in sweatpants? Hit the city streets by topping off your cozy look with a winter coat to provide a structured and tailored contrast to your relaxed sweatpants. If your sweats or fleece pants have a minimalist vibe, give your winter outfit a style boost by incorporating printed pieces and graphic garb. A simple retro sneaker creates the perfect balance for your street-ready ‘fit. And for the final touch, it’s time to mask up, but opt for something that adds to the overall style vibe you’re going for—those disposable face masks just won’t cut it.

City Sweats Essentials

4 Easy Outfits to Wear Anywhere This Winter (13)

Reiss Mirror Black Double Breasted Overcoat

Now 33% Off

4 Easy Outfits to Wear Anywhere This Winter (14)

Men's Recycled Fleece Tapered Sweatpant

4 Easy Outfits to Wear Anywhere This Winter (15)

Reebok Club C 85 Vintage Shoes

4 Easy Outfits to Wear Anywhere This Winter (16)

Tom Ford Face Mask

4 Easy Outfits to Wear Anywhere This Winter (17)

Katie Dupere

Katie Dupere is an editor and writer in New York City specializing in identity, internet culture, social good, lifestyle and beauty topics.

As an expert and enthusiast, I have access to a wide range of information and can provide insights on various topics. While I don't have personal experiences or emotions like a human, I can provide factual information and answer questions based on available data.

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Winter Style Trends for Men

The article discusses winter style trends for men, focusing on comfortable and versatile clothing options. It suggests that the changes in daily dress due to the past two years have made men smarter shoppers, allowing them to invest in winter wardrobe essentials that prioritize comfort and functionality. The article emphasizes the importance of pairing together outfits that are both comfortable and stylish.

WFH, But Polished

The article suggests that even when working from home (WFH), it is beneficial to dress in a more polished and professional manner. This can help create a sense of normalcy and boost confidence. The article recommends incorporating elevated sweaters, true trousers, relaxed-fit chinos, and winter vests into WFH outfits. It also mentions the freedom to go for walks or run errands during the workday, and the importance of wearing comfortable sneakers indoors.

Below Freezing 'Fits

For harsh wintry conditions, the article advises investing in high-quality winter gear. It suggests opting for a quality down jacket that is windproof, waterproof, insulating, and easy to care for. Layering with long-sleeve tees with heat technology and pants with performance fabrication for added stretch and durability is also recommended. Waterproof winter boots with a lug sole for traction are mentioned as a must-have. The article suggests sticking to a color scheme of neutrals, navy, and dark shades of green for a sleek and timeless look.

Winter Workout Warrior

The article acknowledges the importance of taking workouts outdoors during the winter for a refreshing change of scenery. It suggests lightweight gear that provides added warmth without hindering performance. Layering with leggings under workout shorts and wearing a stretchy-yet-insulating puffer jacket is recommended. The article also mentions the importance of simple and stylish graphic running tees.

City Sweats

The article suggests that sweatpants can be stylish when paired with a winter coat to create a structured and tailored contrast. It recommends incorporating printed pieces and graphic garb to boost the style of the outfit. Retro sneakers are mentioned as a perfect balance for a street-ready look. The article also suggests opting for stylish face masks that add to the overall style vibe.

Please note that the information provided above is based on the content of this article. If you have any specific questions or need further information, feel free to ask!

4 Easy Outfits to Wear Anywhere This Winter (2024)
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