The Best Grey Boots – But Why Aren’t There More?

Grey boots are the unsung heroes in the world of men’s footwear. Despite their potential, they seem to always be overlooked by bootmakers, overshadowed by the more conventional blacks and browns.

But compared to black boots, I think grey boots match more easily with blue jeans and they’re easier to wear because it’s easy for black boots to come off as either too dressy or too military coded. (Nothing wrong with that; it just might be a language you don’t want your boots to speak!)

That being said, most people don’t think of grey boots and most brands don’t sell them. Sometimes they’ll do them as one-offs, but then by the time you find an article like this, the boot is no longer for sale. So I’ve spent years coming up with this list of the best grey boots that are as evergreen (evergrey) as possible.

Top Picks for Grey Boot

Our resident boot expert, Nick English shares his favorite grey boots. Every boot on this list is durable, stylish, repairable, and of course, grey.

Most Versatile: Thursday Boot Company’s Captain – Grey Matte

Thursday’s Captain is first on the list because they’re inarguably the best value and most versatile boot.

It boasts quality craftsmanship with its Goodyear welt construction, which practically no other boot shares at the sub-$200 pricepoint. The matte finish keeps it subtle and offers a modern touch, making it suitable for both casual and smart casual wear. (Watch for those luggy soles though, which do dress it down more than the flat-soled Captains.)

Because of the brand’s popularity, they’ve got more resources to try less common leathers, so Thursday also offers grey suede Chelsea that’s worth checking out (I reviewed ’em), as well as this grey Harness boot for guys who like more avant garde looks.

• Why We Love It: Exceptional value at under $200, resoleable, tons of sizes, and a versatile almond toe that dresses up and down pretty easily.
• Considerations: No wide widths, less versatile than the flat-soled Captains, and better suited for casual wear than the dedicated work boot you might be looking for.

Classic Work Boot: Red Wing’s Alpine Portage Muleskinner (Iron Ranger)

The Iron Ranger in Alpine Portage leather is more of a grey-green — fortunately for us, because this kind of grey might be the most versatile.

This boot is the crowning glory of Red Wing Heritage, a brand that makes very tough, very casual boots in Minnesota. The leather is thick and ages wonderfully, just look out for that break in — when they’re new, you’ll want to leave the house with a pair of sneakers in case you need to give your feet a rest.

For a Goodyear welted boot that’s made in America with such high quality leather, the Iron Ranger’s $350 is about as well priced as you can expect. Or, for a less vintage looking boot, check out the Moc Toe, also available in the Alpine Portage leather.

• Why We Love It: Classic American work boot aesthetic, hardwearing leather, made in USA, well priced for what you’re getting.
• Considerations: Firmly casual and can’t be dressed up, has a tough break in.

Best Smart Casual: Grant Stone’s Diesel Storm Kudu

This low profile boot, as we said in our Grant Stone Diesel review, is the king of smart casual. It comes in a range of leathers but their sole grey option has a twist: it’s made of kudu leather. Because this antelope grew up in the wild, kudu leather is known for bearing scars from the animal’s life, which makes every pair unique.

The scars dress down the Diesel a little, sure, but it means these boots strike the perfect balance between smart casual and rugged, and it works wonderfully with a pea coat or a denim jacket.

The grey antelope leather is striking not to mention a conversation starter, and they use this leather on a bunch of other boots like the more work boot-inspired Garrison and even their penny loafers.

• Why We Love It: Very versatile smart casual boot, famously great quality control, kudu leather has tons of character and texture.
• Considerations: The visible scars and scratches might be too casual for some dressier settings.

Best Casual Chelsea: Allen Edmonds’ Grafton

The Grafton from Allen Edmonds is a robust, American-made Chelsea boot that’s functional and stylish, suitable for outdoor adventures and city living alike. This makes it stand out in the realm of Chelseas, which tend to lean dressy.

That said, this model often sells out — but Allen Edmonds is a giant company that has a wide range of other grey boots that include storm-ready moc toes and business casual wingtips.

• Why We Love It: Made in USA, features a waterproof membrane, and comes in a variety of widths, making it practical and comfortable for diverse foot sizes.
• Considerations: Higher price point, suede can be annoying to keep clean, and it’s less dressy than some Chelseas.

Most Versatile Work Boot: Origin USA’s Coronado – Slate

The Coronado in Slate captures the essence of American craftsmanship with its bulky heritage look and hybrid stitchdown construction. There are meatier work boots on this list (keep scrolling if you need something more heavy duty) but the Coronado is the most popular work boot here. That’s likely because of its price, versatility, and frankly, it’s good looking for a work boot.

• Why We Love It: Emphasizes durability and a classic design, made in America and priced under $350.
• Considerations: The bulky design may not appeal to those looking for a more refined or modern look.

Best Monkey Boot: Bridlen’s Monkey Boot

This Monkey Boot stands out with its unusual grey kudu suede and detailed craftsmanship. We visited Bridlen’s factory and were frankly amazed by the quality we encountered there!

Loved by boot aficionados, Bridlen is recognized for its unusual hybrid construction — it’s resoleable, but it’s kind of part hand welt part Goodyear welt, if you want to get nerdy — and they line their boots without using glue, making for an unusually breathable build.

The fact that it’s made in India means it’s remarkably good value at $330, especially considering they use the tannery that’s world renowned as the best for kudu: CF Stead.

• Why We Love It: The lace-to-toe monkey boot style offers a more secure fit, very breathable and durable build, using suede takes care of the kudu’s scars.
• Considerations: The distinct style may not suit everyone.

JK Boots – Forefront

JK Boots’ Forefront (our review, written by a sheet welder) is made in the Pacific Northwest with hardwearing stitchdown construction, and JK has made a name for themselves using far more leather than your typical boot — durability to match. They also use grey leather for some other boots in their collection that are worth checking out!

• Why We Love It: Built like tanks, with the thickest leather uppers you’ll come across, made in USA, resoleable, great arch support, cheaper than many Pacific Northwest competitors.
• Considerations: Sizing is hard to figure out, and expect a 2-3 month lead time if your size isn’t in stock (actually pretty good for a made-to-order work boot)

Custom Grey Boots

It’s worth mentioning that Nick, Stridewise’s founder, was so tired of not finding grey boots that he ended up ordering two pairs of custom grey boots from Indonesia. But I won’t tell you to get them because they’re expensive and take 6 months to arrive… okay it was a Chelsea from Briselblack and a Boondocker from Onderhoud.

Anyway, the brands in this video below (or the article on where to get custom boots) will give you plenty of other ways to find grey boots!

What Do Grey Boots Match With?

I admit that most guys don’t share this opinion about black boots, but I think grey boots pair way better than them with blue jeans — and I think grey boots look way better under black jeans than black boots do because they break up your silhouette.

Grey works with more neutral and monochromatic looks, where color might otherwise be a distraction — monochromatic can mean ‘all shade of black’ here but I find it much more welcome in outfits that are heavy on blue, white, and/or warmer colors like orange and burgundy.

Gray also tends to read more contemporary, so for less rustic, or perhaps even streetwear-oriented looks grey boots have lots of potential. Black boots have a frustrating potential to either fade into the background or look too assertive and serious. Get grey and look like you’ve put in some effort without drawing too much attention.

Wrapping Up: Grey Boots as a Wardrobe Staple

Grey boots might be a bit untraditional, but in a sea of light brown, dark brown, and black, they create a new range of styling possibilities. From casual days out to dressier occasions, grey boots bring an understated uniqueness. Indeed, because of their relative minimalism and lack of hue, grey is an easygoing accompaniment where others might be too busy.

Whether you choose the rugged charm of the Red Wing Iron Ranger or the refined elegance of Allen Edmonds’ Grafton, you are unlikely to walk past anybody else with a pair to match. But you won’t look like you’re trying to stand out.

And as we like to say around here, that’s the space that most guys like to occupy.