Best Men's Red Wing Shoes

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.

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.

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

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.

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.

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

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.

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.

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.

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.

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.

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.

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.

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.