The Best Men's Boots, for Every Style and Occasion

To the untrained eye, boots really aren’t that different from thick-soled, high-top leather sneakers. But the world of welted footwear is astonishingly complex. For over five years, I’ve run a blog and YouTube channel called Stridewise that’s dedicated to exploring the world of men’s boots, and it’s taken me to boot factories and tanneries all over the world. I’ve even made my own boots by hand in Guatemala, and I’m still learning new things.

It’s easy to get too deep into boots and decide you need a pair that costs $800 because the toe box bulges just so, or because the brand uses an extra hard-to-understand construction process. But I know the average guy just wants something durable, cool-looking, and able to keep his socks dry in a storm. And, of course, we all want to make a selection that’s high-quality but won’t cost more than it needs to. With that in mind, here are my criteria for recommending a boot.

• Resoleability: A Goodyear welt is the gold standard for making a boot any cobbler can resole, plus it makes your boot water-resistant enough for any storm. Blake stitches, stitchdown construction, and Blake rapid are examples of less common builds that are harder to get resoled, but it can be done. 
• Full-grain leather: This means the leather hasn’t been sanded down too much, preserving a lot of the animal’s hide. It makes for boots that age well and last a long time.
• A shank: That term refers to a hard piece of material (usually steel) that goes between the heel and midfoot. It makes a boot more stable, reducing the risk of foot pain when you’re standing all day. 
• A leather midsole or insole: Among other benefits, this helps the boot to conform to the shape of your foot, resulting in something that feels like a custom fit over time.

Boots are more stable than sneakers, and whether or not you “work” in yours, a well-built boot is usually a good tool for reducing foot and ankle pain. (Still, talk to your podiatrist if you’re having issues.)

There are as many kinds of boots as there are people and use cases, but here’s a list of my favorites that should help you find one that’s right for you. 

With all the welts, shanks, rands, cork, and labor involved in making welted boots, it’s very rare for a good pair to cost under $300. That’s why it would be a disservice to not tell you about Thursday Boot Company, because the well-respected brand has  managed to keep its flagship model available for less than than $200 since day one.

This affordability for the quality has earned the brand immense popularity, and with that comes a wide range of leathers and soles, plenty of models for wide feet, and a customer-focused policy of free returns and exchanges.

The Captain is a streamlined cap toe boot that’s intended to combine the best of dress and work boots, so it’s not as bulky as what you’ll find on factory floors. These stellar, versatile boots also have an outdoor-to-city look and fit well into a modern wardrobe—plus they have poron insoles, which means they absorb shock better than most boots on the market. 

Founded in 1905 in Red Wing, Minnesota, where the brand still make all its boots today, Red Wing is an institution that’s unparalleled in the world of good boots.With its flagship product,  it essentially invented the moc toe work boot. It’s firmly casual while also being incredibly high-quality, making it a great accent to any informal style, from workwear to streetwear to lumberjack.

The company also has the rare distinction of owning both its factory and its own tannery, which means Red Wing has great consistency and quality control. The leather is very thick and you can expect a tricky break-in process, but after a week or two of wear, they start to soften and pick up the kind of patina that money can’t buy. Despite this, the price is still very impressive for an American-made boot. (Trust me, I’ve looked at the alternatives.) 

There’s no reason to shun dress boots—like I said, foot and ankle stability is a good thing! With more than 2 million pairs sold, Allen Edmonds’ Park Avenue Oxford has earned its reputation as America’s go-to dress shoe, so it’s a no-brainer that the brand’s new Park Avenue boot is the ideal suit boot.

Dress footwear tends to have a lot of rules, and the Park Avenue follows them: There are blind eyelets (meaning you don’t see the eyelets’ shiny metal on the outside of the lace panel), closed lacing (the facing is stitched on top of the vamp), and calfskin leather (which creases more finely than cowhide).

Don’t sweat the leather soles; while they’re not great in the rain, they’re immensely comfortable and breathe very well in the heat. 

If you’re looking for a boot that’s great for business casual or date night, Grant Stone has built its brand around extraordinarily high-quality boots with designs that pair perfectly with either aesthetic. The flagship Diesel boot is a no-frills service boot: low profile, uncomplicated, and only a little sleek.

The company really shines with its leather selection: the previous brands stick with one or two tanneries, but Grant Stone uses hides from a wide variety that are universally celebrated for their quality: Chicago’s Horween, England’s C.F. Stead, and Italy’s Badalassi Carlo to name a few. The brand’s not afraid to branch out with unusual offerings, either;  it offers Diesels made of antelope, kangaroo, and even ostrich, depending on the season. 

Grant Stone has an interesting business model: it’s owned and operated by American Wyatt Gilmore and its products are made in a small facility in Xiamen, China, where Gilmore spent eight years living and refining his craftt. But the boots' only Chinese component is the shoebox, and their quality is undisputed among the nerdiest of boot nerds. While they’re not cheap, they’re the kinds of boots that would cost more than $600 if made in the USA.

To be clear: most guys don’t need waterproof boots. Goodyear welts, as discussed, are perfectly water-resistant and will handle almost any puddle. But if you’re looking for the kind of boot that can let you stand in mud for hours on end, Ariat’s Wexford is it.

The main reason? They’re one of the very few waterproof boots that don’t look like New England galoshes. The Wexford makes the ‘waterproof’ category by virtue of the waterproof membrane running beneath the full-grain leather upper, though this doesn’t give it the undue bulk of some of its competitors. 

I’ve stood in many puddles testing the waterproofness of my Wexfords and always came away bone dry. And with a design that’s subtle and casual, nobody needs to know you’re wearing performance boots. 

Note that this boot’s construction isn’t resoleable; if you want waterproof, you usually need to sacrifice that element.  

Perhaps because this laceless design is more often associated with dressier footwear, it’s hard to find a good, resoleable Chelsea for less than $500. So I was happy to encounter Koio’s Trento, a sleek and versatile boot that manages to come in just shy of $400. The Trento dresses up and down easily, which is exactly what you want from a Chelsea. 

Fully made in Italy, the European style cues include a streamlined silhouette and Blake stitch construction. More common in Europe, Blake stitches are a little less water-resistant than a Goodyear welt is, but they’re lighter, more flexible, less costly to produce, and resoleable.

Koio puts a ton of emphasis on sustainability, too, only using leather that’s gold rated by the Leather Working Group, an industry watchdog that ensures your tannery isn’t one that pollutes waterways and harms workers (an all-too-common phenomenon in poorly regulated tanneries). 

That does it for my favorite casual and not-so-casual boots for men. Between chunky moc toes, versatile lace ups, and sleek slip-ons, there’s something here for every guy looking to add some style to his winter wardrobe.

And remember that with sturdy builds and resoleable construction, these boots will last season after season, giving you a healthy return on your investment. Trudge onward into 2024 (and look good doing it). 

The Rec Room staff independently selected all of the stuff featured in this story. Want more reviews, recommendations, and red-hot deals? Sign up for our newsletter.