Best Casual Boots for Men

As of November 2019


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what we like

  • The comfiest shoes we have ever worn
  • Look great with all pants/jeans
  • Versatile enough to dress up for work or dress down for a casual dinner
  • Easy to wash and clean
  • Free shipping
  • Free 30-day returns (even if worn)
  • As a certified B corp, Allbirds prioritizes using environmentally friendly materials

keep in mind

  • The colors come and go. They tend to only keep a handful of “Classics” colors and a variety of limited edition ones
  • Shoe laces can tie a little loose meaning double knots are necessary otherwise they will come undone
  • No half sizes (if in doubt, size up)
  • Never go on sale
  • Otherwise, this is a no brainer


There is close to a 100% chance you’ve already seen an ad for these or read a tweet by a venture capital bro praising them. We are here to assure you that the hype is real is and justified.


This is admittedly a very broad category of shoe which could encompass everything from Chelsea boots to Chukkas. Pretty much every clothing company out there, including Zara and H&M, makes a respectable version of casual boots which fit the bill. But in keeping with our universal theme of simplicity, we just are looking to answer the question of whether or not there is one out there which consistently looks good with any pair of pants while being dynamic enough to wear for most occasions.


We feel fairly confident in saying that you won’t find a more comfortable pair of shoes on the market than the Tree Toppers. We also think the Tree Topper style is super sleek and looks great paired with any jeans or pants. If you don’t already own a pair, fight back your urge to be contrarian and just try one. There is literally no risk. Shipping is free and returns are free for 30-days, even if worn.

Sizing Tips & FAQs

What’s the return policy?

Allbirds has one of the more customer friendly return policies we have seen. Returns are free and can be done within 30 days, even if the shoes are worn.


What’s the difference between the Tree Toppers and the Runner Ups?

Tree Toppers are lighter and made out of eucalyptus tree fiber. Since the materials offer a cooling effect, it’s best for any non-winter weather climate. The Runner Ups are made of wool and are actually our choice for Best Winter Boots.


How do you wash them?

You can just pop them in the machine if they get dirty. Remove the sole and laces, place them in a linen bag and use cold water. Do NOT put them in the dryer (let them air dry)


What makes Allbirds so environmentally friendly?

Their Wool Runners are made of sheep’s wool. Sheep need regular haircuts which makes it a mutually beneficial symbiotic relationship. Since 2016 they’ve claimed to have given approximately 45,000 sheep a much-needed haircut. Each pair of Allbirds laces is made from one post-consumer recycled water bottle. Finally, the Tree Toppers are made from a proprietary formula using eucalyptus trees.


Have another question?

Related Products & Links

H&M Boots | Zara Boots

There are a few things that H&M and Zara do very well and their footwear is one of them. They are definitely worth checking out if the Allbirds design isn’t quite your look and you’re searching for more of a Chelsea or Desert boot and/or something dressier. You’ll find designs on each site which might cost 3-5x more if you bought a similar one from a high end designer like Ferragamo. In my experience, H&M and Zara boots tend to hold up well overtime.


Chuck Taylor All-Stars

Forever a classic. The White Monochrome versions pair well with any pair of slim fitting joggers/pants. Great price under $60. Just not very comfortable at all, particularly when compared to the All Birds.


Nike Blazer Mid ’77 Vintage

Another absolute classic shoe which pairs extremely well with slim fitting pants. More comfortable and cushioned than Chuck Taylors. Obviously, these are more casual and don’t dress up as well as All Birds.

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