The 7 Most Comfortable Men’s Work Boots Will Make it Feel Like You’re Not Working At All

Timberland Basic 6-Inch Boot
Courtesy of Timberland
When you buy something through our retail links, we may earn commission and the retailer may receive certain auditable data for accounting purposes.

No matter what you do for a living, there’s one thing everyone with a job can agree upon: work sucks. But, for those working in trades that involve manual labor such as construction, electric, welding and more, us in the office can all likely agree you guys were handed the shit end of the stick. Sure, you probably make a ton of money and have met a lot of good buddies over the year, but keeping on your toes all day must be a nightmare. This is why we’re suggesting you ditch whatever you slip on your foot every day with some of the most comfortable men’s work boots.

Keeping your feet at ease isn’t as difficult as you may think when you have the most comfortable men’s work boots. Some of these make for the best shoes for standing all day and we all know damn well you’re doing more than that at work. No matter the weather or working conditions, the most comfortable work boots will keep your feet dry and supported fun sun up until sundown.

Dear Santa... %title% %title% List Price:%original_price% Price:%price% You Save:%discount_amount% (%discount_percent%) Shop NowCoupon Code: %coupon_code% SPY may receive a commission.

A pair of work boots that make for some of the most comfortable men’s shoes feels like a no-brainer. And, yeah, they’ll still keep your feet safe. Check out all of our favorites below and save your foot from being too tired after a long day at work.

1. Timberland Basic 6-Inch Boot

BEST OVERALL

Shocked? We didn’t think so. Timberland creates the work boot of all work boots and it’s no surprise as to why. The entire exterior is waterproof to lessen the chance for water, mud and snow to get inside where your socks are. Each boot’s collar is padded to help keep you sturdy and ensure your ankles feel comfortable when walking around. Timberland also uses fabric lining and a round-toe design for added comfort no matter where your workday takes you. You don’t have to be afraid to get these muddy, either. They’re relatively easy to clean and even a pair of dirty Tims are a pair of cool Tims.

Timberland Basic 6-Inch Boot Courtesy of DSW

Timberland Basic 6-Inch Boot

$167.99

  

2. Avenger Work Boots A7244 Composite Safety Toe

RUNNER UP

Comfort and protection should be the top two factors you need to consider when purchasing the most comfortable men’s work boots, and lucky for you, this option from Avenger Work Boots prioritizes both. Each boot uses an EVA footbed to ensure your feet keep cozy throughout your day with a complete rubber outsole for slip and oil resistance. The toes have a lightweight composite safety toe cap that doesn’t go off in metal detectors nor does it transmit any hot or cold temperatures. The exterior is abrasion and water-resistant, too, meaning that you’ll likely be slipping these on your feet for years to come.

Avenger Work Boots A7244 Composite Safety Toe Courtesy of Zappos

Avenger Work Boots A7244 Composite Safety Toe

$101.99

  

3. Irish Setter Wingshooter ST-83632 Work Boot

PROFESSIONAL CHOICE

Most of the time, a recommendation from your buddy in the field could be the best of them all, which is why we had to chat with Shelly & Sands skilled laborer Ben Porter and get his opinion. “I build highways for a living, so I’ve tried just about every big work boot brand you can think of. That said, I’ve found nothing better than the Irish Setter Wingshooter ST-83632 Work Boots,” explains Porter, “every other work boot I’ve worn would take weeks to break in and cover my feet and legs with blisters — but these aren’t like that at all. They’re so comfortable and durable that I’ve been wearing ’em for two years now. There was zero break-in period and I’ve even convinced a couple of the guys at work to get a pair for themselves.”

Irish Setter Men's Wingshooter ST-83632 Work Boot Courtesy of Amazon

Irish Setter Wingshooter ST-83632 Work Boot

  

4. Keen Utility Portland Waterproof Work Boots

MOST FLEXIBLE

While all of the most comfortable men’s work boots should have a little bit of flex, the Portlands from Keen Utility’s malleable properties are most certainly something to rave about. These American-built boots use materials from around the world to create one of the most flexible lace-ups the work boot world has ever seen. Bending up to three times more than a traditional work boot, each boot makes keeping on your feet all day a true breeze. The boots use a premium leather upper that’s completely waterproof and is topped off with carbon composite safety toes at the end of each foot.

Keen Utility Portland Waterproof Work Boots Courtesy of Zappos

Keen Utility Portland Waterproof Work Boots

$229.95

  

5. Red Wing Heritage 6″ Moc Toe Work Boots

MOST TIMELESS

Wearers of Red Wing swear by the brand so much that you can meet guys out on the field who’ve worked wearing nothing else but Red Wings on their feet for decades. These work boots are a staple to trade jobs, making them an instant classic just about any hard-working dude can recognize. With a gorgeous, water-repellent leather, the 6″ moc toes keep wetness out and ensure you keep in style even on the job. Each boot has a full leather footbed that molds to the shape of your foot over time for a customized fit you deserve.

Red Wing Heritage 6" Moc Toe Work Boots Courtesy of Zappos

Red Wing Heritage 6

$279.99

  

6. L.L.Bean Stonington Boots Moc-Toe Work Boots

MOST CASUAL

If you want to take your work boot look to the bars after the day is over, opt for a work boot that can make sense wearing off-site. This classic work boot is evolved for sneaker-like comfort with running shoe flexibility and a durable exterior. They’re created using powerful Nor’easter leather to diminish weather-related issues and stains. Each boot is complete with an EVA mid and outsole, making them so lightweight that won’t even feel like you’re lugging your feet around all day.

L.L.Bean Stonington Boots Moc-Toe Work Boots Courtesy of L.L.Bean

L.L.Bean Stonington Boots Moc-Toe Work Boots

$139.00

  

7. BRUNT Marin Work Boot

BEST NEW-AGE

Fashion is changing, and we’re not only talking about tees, jeans and sneakers. BRUNT’s Marin work boot is the ideal work boot for any new-age dude looking to dip his toes into something a little more revolutionary. Whether you’re a project manager, plumber, electrician, welding or whatever else, the versatility and comfort within these babies make them a reliable opinion your feet are going to love. Each boot is designed to keep you protected from any environment you place yourself into by staying durable, electric-proof and both slip and oil resistant. Getting the job done doesn’t have to mean ditching comfort ever again.

BRUNT Marin Work Boot Courtesy of BRUNT

BRUNT Marin Work Boot

$135.00

  

The Best Duck Boots for Men Will Never Go Out of Style

  

Love what you’re seeing? Follow us on Twitter, Instagram and Facebook and be the first to hear about new product launches, the latest trends and can’t miss deals you won’t find anywhere else.