Merge Work and Play With the Best Winter Gear from Carhartt, the Brand That Makes It Easy To Look Cool

Mens' Carhartt Clothes
Courtesy of Amazon
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Carhartt has been a staple of the working man for generations. Having begun its line of durable clothing in 1889, this iconic brand has been seen on the backs of hardworking men and women in blue-collar trades for well over 100 years. Like Levi’s or Red Wing, it’s an iconic American brand that’s beloved by pretty much everyone. After over 120 years, Carhartt is still worn by people that work with their hands for a living, and to this day it’s popular with metal workers, electricians, sanitation workers and all types of working folk. Carhartt is also widely appreciated in the world of street style, and the brand has found loyal fans among urban hipsters all over the country. Basically, for work or play, there’s Carhartt.

That’s why we decided to create this Carhartt style guide. But, here’s the thing: Carhartt makes no-nonsense clothing that’s as down-to-earth as the people who wear it. If you’re wondering how to perfectly style your Carhartt gear, then you’re kind of missing the point, my man.


How Do You Style Carhartt? However the Hell You Want!

Don’t overthink this: If you want to add a Carhartt beanie, sweatshirt or pants to your daily outfit, just go for it! In general, we’d recommend wearing one piece of Carhartt clothing at a time for social occasions. Go ahead and throw on a Carhartt sweatshirt over your favorite men’s t-shirt and Levi’s. Or trade in your Levi’s for comfortable Carhartt work pants, then finish off your look with a comfy hoodie. That’s really all there is to it.

Of course, the 1-item rule above most definitely does not include the signature Carhartt beanie, which can be worn whenever the hell you want with whatever the hell you want.

These guys get it:


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Carhartt first became popular as everyday wear for the non-blue-collar type in the 70s and 80s when hip-hop artists began sporting the brand in music videos and photoshoots. The sturdy, oversized, baggy look appealed to a lot of guys. Best of all, Carhartt never tried to be something it wasn’t. The company kept on making durable workwear that simply looked great and didn’t cost too much. Eventually, Carhartt was adopted by everyone from 90s skater kids to 2020 e-boys. There aren’t many apparel companies with such wide, enduring appeal.

As trends evolve, Carhartt doesn’t, which is why this timeless brand has maintained so much love for so long. Any kind of person can wear Carhartt whether they’re working or not. It’s more or less a style that has the ability to perfectly morph into any kind of daily wear.

Looking to snag yourself some Carhartt to throw into your winter style? you’ve come to the right place. Read on and check out our new 2020-2021 Carhartt style guide and get a few of our favorite menswear pieces from this iconic American brand.


1. Carhartt Men’s Acrylic Watch Hat A18


Starting at the head, this beanie is a Carhartt classic. (It’s also a great stocking stuffer for Christmas.) This 100% acrylic hat is as easy as it gets in terms of style. The signature Carhartt beanie sports a solid color and the iconic Carhartt logo at the brim. It’s super warm and perfect to rock in colder weather, making it easy to incorporate into your daily look. While we have a soft spot for this classic black option, color ranges from darker blues to fluorescent highlighter yellows. And, of course, there’s the always popular orange Carhartt beanie, perfect for men and women alike.

Carhartt Men's Acrylic Watch Hat A18 Courtesy of Amazon

Carhartt Men's Acrylic Watch Hat A18



2. Carhartt Workwear Jersey Pocket Long-Sleeve Shirt K126


While we also love Carhartt’s pocket tee, since the temperature’s dropping, we recommend you snag this long-sleeve shirt for all your cold-weather needs. It’s made from 100% cotton and has a relaxed fit for an easy fit whether you’re working in it or wearing it on the streets. Worried they won’t have your size? Don’t. There are choices completely out the wazoo, featuring picks from small to 4XL. They even have each size available in a tall option, too.

Carhartt Workwear Jersey Pocket Long-Sleeve Shirt K126 Courtesy of Amazon

Carhartt Workwear Jersey Pocket Long-Sleeve Shirt K126



3. Carhartt Midweight Sleeve Logo Hooded Sweatshirt


When the weather calls for layers, this midweight logo hoodie is a great way to stay warm and cozy in true Carhartt fashion this season. It has an easy pull-on closure the way any other pullover would and has an easy kangaroo pocket to keep valuables or your hands when they’re cold. Unlike the majority of Carhartt’s clothing, this sweatshirt takes it the extra mile by adding the brand’s name on one of the arms. While we love this black option, there are so many more colors available.

Carhartt Midweight Sleeve Logo Hooded Sweatshirt Courtesy of Amazon

Carhartt Midweight Sleeve Logo Hooded Sweatshirt



4. Carhartt Quilted Flannel Lined Duck Active Jacket


When it’s time to bundle on up and head into the cold abyss that is the world we live in, don’t sacrifice style to keep yourself warm. This quilted flannel lined jacket from Carhartt is both extra warming and handsome enough to rock for work and play. It has a drawstring hood for extra protection from the wind or any wet weather that might be in the forecast and it’s made from 100% cotton. This jacket doesn’t look like much, but upon receiving, you’ll quickly realize just how heavy this thing is and how capable it is at keeping you warm. It even has a split kangaroo pocket in the front for keeping valuables.

Carhartt Quilted Flannel Lined Duck Active Jacket Courtesy of Amazon

Carhartt Quilted Flannel Lined Duck Active Jacket



5. Carhartt Rugged Flex Rigby Dungaree Pant


Looking put-together in your work clothes just got even easier with Carhartt’s rugged dungaree pants. These almost casual-looking pants resemble your favorite pair of chinos and look great infused into your everyday look. Merge them with a classic tee and flannel combo or wear it with your favorite sweatshirt. Unlike a majority of Carhartt’s pants, these babies are actually pretty stretchy so you can move around as much as you’d like in them. These pants are ideal for anyone that goes between an office and a job site; they double as both durable workwear and professional, office-ready apparel.

Carhartt Rugged Flex Rigby Dungaree Pant Courtesy of Amazon

Carhartt Rugged Flex Rigby Dungaree Pant



6. Carhartt Relaxed Fit Washed Twill Dungaree Pant


Take your classic work pants to the next level with these relaxed fit dungarees that feature multiple pockets throughout the legs. Yeah, they have the traditional four-pocket design you’re used to, but also contain a couple of pockets on the legs to give you more of a cargo look. While these are perfect for working dudes, we also love these in our casual day-to-day style by rolling them at the bottoms and throwing on a pair of Converse hi-tops. Throw on your favorite hoodie to finish up the look.

Carhartt Relaxed Fit Washed Twill Dungaree Pant Courtesy of Amazon

Carhartt Relaxed Fit Washed Twill Dungaree Pant



7. Carhartt Rugged Flex Relaxed Straight Leg Jean


No wardrobe is complete without at least a couple of handsome pairs of jeans. If you’re looking to snag a new pair for your dresser, check out Carhartt’s rugged relaxed straight jeans with a little bit of wiggle room for easy stretching and moveability. These babies sit slightly below the waist and have the ability to fit right over boots with ease. They’re a ton more durable than most jean brands and look handsome on the body.

Carhartt Rugged Flex Relaxed Straight Leg Jean Courtesy of Amazon

Carhartt Rugged Flex Relaxed Straight Leg Jean



8. Carhartt Zip To Thigh Bib Overall Unlined R37


Have you checked out the overalls trend yet? Because if not, you’re late. But, you’re lucky, it hasn’t died out and we don’t think it’s anywhere close to. These bib overalls are excellent for work, because, well, they’re overalls. But, these are also excellent for wearing on the street over a hoodie with some sneaks. These really up the ante of the Carhartt aesthetic in streetwear and abolish the “made work work” notion entirely when worn correctly. So, why not try it out?

Carhartt Zip To Thigh Bib Overall Unlined R37 Courtesy of Amazon

Carhartt Zip To Thigh Bib Overall Unlined R37



9. Carhartt All-season Cotton Crew Work Socks


When it comes to keeping your feet warm, work socks are the socks. Think about it: Dudes who wear these traditionally for their blue-collar jobs typically have to face some crappy weather conditions in their day, meaning these babies have the ability to keep them warm all day. Try these out for yourself this winter and really understand what we’re talking about. We promise, your tootsies will never be cold again.

Carhartt All-season Cotton Crew Work Socks Courtesy of Amazon

Carhartt All-season Cotton Crew Work Socks



10. Carhartt Cmw6095 6″ Casual Wedge Work Boot


Keep your feet covered and secure no matter what you put them through. These 100% leather bad boys are made with a storm defender waterproof breathable membrane to keep your feet dry even in a hurricane. They have a soft toe, so guys wearing these while working, note that they might not protect from any heavy falls. For dudes looking to incorporate these into their everyday style this winter, we suggest pairing with your most rugged-looking jeans and a henley for an effortlessly cool look.

Carhartt Cmw6095 6" Casual Wedge Work Boot Courtesy of Amazon

Carhartt Cmw6095 6

$149.95 $159.99 6% OFF


11. Carhartt Legacy Deluxe Work Backpack


Tie it all together with this easy to carry, deluxe work backpack ready to hold all of your most important belongings. Whether you’re carrying tools, books, your laptop or a change of clothes, just about anything can fit inside. The backpack has various pockets to keep things safe and even has a padded laptop holder inside large enough to fit a 17-inch Macbook. Raining outside? Don’t worry, all your contents will stay safe due to the pack’s water-repellant Carhartt Rain Defender.

Carhartt Legacy Deluxe Work Backpack Courtesy of Amazon

Carhartt Legacy Deluxe Work Backpack