Best Men's Red Wing Shoes

Updated December 2019
Why trust BestReviews?
BestReviews spends thousands of hours researching, analyzing, and testing products to recommend the best picks for most consumers. We only make money if you purchase a product through our links, and we never accept free products from manufacturers. Read more  
BestReviews spends thousands of hours researching, analyzing, and testing products to recommend the best picks for most consumers. We only make money if you purchase a product through our links, and we never accept free products from manufacturers. Read more  
BestReviews spends thousands of hours researching, analyzing, and testing products to recommend the best picks for most consumers. We buy all products with our own funds, and we never accept free products from manufacturers.Read more 
Bottom Line
Pros
Cons
Best of the Best
Red Wing Heritage Men's Classic Oxford
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 shoe by Red Wing and will complete almost any look.

Pros

Handsome shoes with excellent tread. Look 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.

Red Wing Heritage Men's Classic Moc 6" Boot
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. Offer classic looks; 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.

Best Bang for the Buck
Red Wing Heritage Men's Weekender Oxford Work Shoe
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 Iron Ranger 6" Lug Boot
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 1/2 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
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.

Why trust BestReviews?
BestReviews spends thousands of hours researching, analyzing, and testing products to recommend the best picks for most consumers. We only make money if you purchase a product through our links, and we never accept free products from manufacturers. Read more  
BestReviews spends thousands of hours researching, analyzing, and testing products to recommend the best picks for most consumers. We only make money if you purchase a product through our links, and we never accept free products from manufacturers. Read more  
BestReviews spends thousands of hours researching, analyzing, and testing products to recommend the best picks for most consumers. We buy all products with our own funds, and we never accept free products from manufacturers.Read more 
How we decided

We purchase every product we review with our own funds — we never accept anything from product manufacturers.

17 Models Considered
8 Hours Researched
1 Experts Interviewed
150 Consumers Consulted
Zero products received from manufacturers.

We purchase every product we review with our own funds — we never accept anything from product manufacturers.

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.

The team that worked on this review
  • Jennifer
    Jennifer
    Writer
  • Melinda
    Melinda
    Web Producer
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Red Wing

Heritage Men's Classic Oxford

Red Wing

Heritage Men's Classic Oxford

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 shoe by Red Wing and will complete almost any look.

$208
×

Red Wing

Heritage Men's Classic Moc 6" Boot

Red Wing

Heritage Men's Classic Moc 6" Boot

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.

$242
×

Red Wing

Heritage Men's Weekender Oxford Work Shoe

Red Wing

Heritage Men's Weekender Oxford Work Shoe

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.

$167
×

Red Wing

Heritage Men's Iron Ranger 6" Lug Boot

Red Wing

Heritage Men's Iron Ranger 6" Lug Boot

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.
$260
×

Red Wing

Heritage Men's Foreman Chukka Lace Up

Red Wing

Heritage Men's Foreman Chukka Lace Up

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.

$284

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