Best Men's Red Wing Shoes

Updated October 2020

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Bottom Line

Pros

Cons

Best of the Best

Red Wing

Heritage Men's Classic Oxford

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Bottom Line

Once you determine the best size for you, these sleek, rounded toe oxfords will fit your style, whatever that may be. These are the most versatile shoes by Red Wing and will complete almost any look.

Pros

Handsome shoes with excellent tread. Looks great with numerous fashions, from jeans to work wear. Also ideal for casual wear or semi-dressy attire. Crafted with quality in mind, which is typical of the brand. Several color options.

Cons

Size unpredictability is common; they tend to fit too narrow or too large, and may seem longer in the toe than most shoes.

Best Bang for the Buck

Red Wing

Heritage Men's Weekender Oxford Work Shoe

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Bottom Line

These shoes offer Red Wing's superior construction in a versatile style for a price that falls at the lower end of the brand's range. Hands down the best value on our shortlist.

Pros

Men who want a comfortable pair of shoes for work, casual, or semi-dressy wear will be impressed by these shoes, as the classic oxford style and handsome, leather workmanship pairs perfectly with numerous fashions and occasions.

Cons

The fit runs quite large, and the shoes may stretch a bit with wear, causing the size to feel even larger over time. The pointed toes look nice, but may bother some men with various foot issues.

Red Wing

Heritage Men's Classic Moc 6" Boot

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Bottom Line

A good-looking pair of boots, but they seem to have more going for them when it comes to aesthetics versus durability, comfort, and fit.

Pros

These attractive boots come in several colors, which make them a great match for almost any outfit you'd like to pair with boots. Offers classic look; reliable tread.

Cons

Some owners gripe about durability issues such as flimsy leather and fraying seams, which spark authenticity concerns. Known to rub on the calf muscles. Size discrepancies; fits some men too narrow, but many more too large.

Red Wing

Heritage Men's Iron Ranger 6" Lug Boot

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Bottom Line

You may want to invest in the Iron Rangers, one of Red Wing's most popular styles, if you need durable work boots. But other options on our list are more practical for other occasions and less pricey.

Pros

Ideal for men who need a well-made pair of boots for work thanks to the comfortable fit, rugged soles, and precisely crafted leather. They also look good with jeans and other casual trousers.

Cons

On the higher end of the price range. They run around a half size large, but this is typical of the brand. At least a few defective pairs have been reported.

Red Wing

Heritage Men's Foreman Chukka Lace Up

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Bottom Line

Minor quirks aside, these Red Wings are made for men who want more than a shoe but a pair that's shorter in the ankle than traditional boots.

Pros

A must-have for men who want casual boots that look good and are less bulky than typical styles, as the chukka design is fairly lightweight and easy to wear. Also ideal for work wear, as the durable soles are perfect for men who are on their feet all day.

Cons

While most Red Wings run large, the slightly narrow toe may make these fit a bit tightly for some wearers. Break-in period could take a few weeks, as the leather is still at first.

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Love the idea of wearing work boots all the time but still looking appropriate in just about any setting? Then Red Wing shoes are a solid choice for you. Whether you want a classic short work boot or a dressier looking oxford, Red Wing’s shoes are built to withstand a lot of rough terrain and construction-site conditions – regardless if you’re on a messy jobsite or in a polished office. The Heritage collection is your go-to if you want the oxford option; otherwise we recommend traditional Red Wing work boots. These aren’t cheap, but that means you’re paying for quality footwear that will last through years of rough wear.

Other Products We Considered

The BestReviews editorial team researches hundreds of products based on consumer reviews, brand quality, and value. We then choose a shorter list for in-depth research and testing before finalizing our top picks. These are the products we considered that ultimately didn't make our top 5.

Red Wing

Heritage Men's Work Chukka

Red Wing

Heritage Men's Moc 6" Boot

Red Wing

Heritage Men's Chelsea Pull On

Red Wing

Heritage Men's Weekender Chukka Boot

Red Wing

Men's Weekender Chelsea Suede Boots

Red Wing

Heritage Men's Iron Ranger 6" Vibram Boot