Top 5 Casual Boots for Men

5. Chippewa Service Utility Boots


Extremely affordable, functional , and stylish. I would say Chippewa boots are probably the best bang for your buck when it comes to a nice work/motorcycle boot. Similar style to Red Wing and great quality control when it comes to construction and leather. If you are looking for a resoleable American made workboot then you can’t go wrong with Chippewa. Before my current Iron Rangers, I wore the 6-inch service utility boot for years.

Some things to keep in mind:

  • They are quite heavy but well made
  • It takes a considerable amount of time to break in compared to other boots

4. Clarks Desert Chukka Boots


Offers a unique style that is extremely comfortable and easy to wear. Compared to the other options in this list, these boots are by far the easiest to break into. The leather is soft and easy to maintain. If you are looking for a boot with character and decent quality, then I highly recommend the Clarks Desert Boots. I would highly recommend the Beeswax color variant.

Some things to keep in mind:

  • The color changes drastically with wear and conditioning
  • Not as durable and high quality as the other options in this list
  • Synthetic soles are quite slippery and require resoling much more often than other options

3. Red Wing Classic Moc 6″ Boots


Great quality, unique look, and extremely durable. Red Wing Moc-toe boots are a great casual edition to any wardrobe. With these, you get the rugged look and Red Wing quality. These boots are built to last and the welt construction adds to the strength and durability. Great daily boots.

Some things to keep in mind:

  • Buy half size to full size lower
  • Not the most comfortable insoles so you might want to replace them
  • It takes a good amount of time to break in
  • Thick socks (as pictured) really help if you decide to stick with the leather insoles

2. Wolverine 1000 Mile Boots


Casual but still dressy enough for formal events like weddings etc. I would say the main reason to go for these boots is if you favor a more fashionable look than the work/construction style of my other casual picks. Wolverine 1000 mile boots are high quality, American made, and as long as you take of them with proper conditioning/seasonal oiling, then they’ll last you years. After breaking in, these boots mold extremely well to your feet.

Some things to keep in mind:

  • Goodyear welt construction allows for easy resoling.
  • Flat soles are slippery in inclement weather and have no tread
  • Expensive due to their build quality and dressy look

1. Red Wing Iron Ranger Boots


In my opinion, the Red Wing Iron Rangers are the best all round casual boot. They may be higher in price than other options but they boast high quality construction, comfort, and style. These boots will easily last a lifetime with proper care and conditioning. I simply condition mine with refined coconut oil every 6 or so months. As you wear and condition these, they gain so much character.

The cap toe design adds to the strength and longevity of these boots and the Goodyear welt construction allows for easy resoling. This is an exceptional boot. Most people don’t recommend wearing boots daily, but I have worn mine daily for several years and they just get better and better. The trick here is to get a good quality shoe tree like these from Allen Edmonds. They absorb moisture, sweat, and eliminate any odor.

These boots offer a timeless style. You really can’t go wrong with them.

Some things to keep in mind:

  • The standard width is quite narrow so I went with the wider option.
  • These run large so size down 1-1.5 sizes. For example, I wear a 10 in vans and 9 in Red Wings.
  • Takes a little time to break in (2-4 weeks) but is extremely comfortable afterwards.


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