Earlier in 2022, I came across this unique pair of Chelsea boots during my research and had to give them a try.
Before then, I used to wear my old pair for long walks around some of London’s fanciest areas, and while they looked stylish enough, there was always one major problem:
Comfort.
My Nike trainers handled walking much better, but they didn’t always suit the environments or outfits I wanted to wear. So I started looking for something that could balance both worlds: footwear that was stylish enough for city life, yet comfortable and durable enough for long hours on foot.
The result?
Blundstone.
But before buying any product, I always like understanding the story behind the brand rather than simply following hype.
Brief history and where Blundstone boots are made
Blundstone has been around since 1870. The company was founded in Tasmania, Australia, by John Blundstone, a British migrant who moved from England with his wife in 1855.
John initially worked as a coach-builder before later importing shoes from England and eventually manufacturing boots in Hobart’s Liverpool Street. By 1892, his eldest son joined the business, leading to the name John Blundstone & Son.
Today, Blundstone boots are manufactured overseas in countries including China, India, Mexico, and Vietnam, while the company’s gumboots are still produced in Hobart.
That’s the history in summary, but what interested me most was whether the boots themselves actually lived up to their reputation.
Style, materials and features
The boots arrived in a navy and brown box, and I ordered them in a UK size 8, which converts to a US 9 and EU 42.
At the time, they cost me around £155 including taxes, roughly $200 or €183.
I chose the #585 Rustic Brown from the brand’s Classic series because, visually, they immediately stood out to me. Blundstone offers several colours and variations under the range, but the rustic brown felt like the perfect balance between rugged and versatile.
Inside the box came the boots, a care guide, and two additional footbeds/insoles.
The first thing I noticed after unboxing them was how solid and practical they felt.
The uppers are made from waxed nubuck leather, which gives the boots that slightly rugged, worn-in appearance straight out of the box. Unlike polished smooth leather, which can sometimes feel overly formal or delicate, the waxed nubuck hides creases and marks much more naturally over time. They’re also water-resistant with thinsulate insulation for colder weather.
Living in the UK, where rain is almost unavoidable, those details quickly became genuinely useful rather than just marketing points.
Inside, the boots combine leather and textile lining with a contoured EVA insole designed for shock absorption and everyday comfort.
The elastic side panels also felt firmly stitched, and the boots overall looked built for actual use rather than just appearance.
Compared to many slimmer Chelsea boots, the Blundstones have a slightly chunkier and more rugged silhouette, which naturally makes them lean more casual stylistically, but not in a way that feels limiting or difficult to style. Personally, I found they worked best with jeans, chinos, corduroy trousers, cargos, and other relaxed smart-casual outfits.
Another thing I appreciated was the grip underneath the boots. The rough-textured outsoles handled slippery pavements and wet surfaces surprisingly well.
As mentioned earlier, comfort was the biggest reason I bought these boots in the first place, so naturally, I decided to test them properly almost immediately.
The day after receiving them, I wore them around Victoria, Oxford Street, and Knightsbridge in London. The goal was simple: test the comfort, test the sizing, and see how they handled colder weather conditions.
The first impression was honestly very positive.
For nearly seven hours, I walked around shopping areas, stood on buses and underground trains, and experienced almost no discomfort whatsoever.
That first-day comfort genuinely impressed me.
Unlike many leather boots that require painful break-in periods, the Blundstones felt supportive and wearable almost immediately. The extra footbeds included in the box also turned out to be unnecessary because the sizing fit me perfectly straight away.
The Thinsulate insulation also helped noticeably given how cold it was that day, making the boots feel warm without becoming overly heavy.
However, my opinion on comfort became more nuanced over time.
While the boots remained excellent for casual everyday wear, commuting, shorter outings, and moderate walking, I eventually realised they weren’t quite as ideal for long-distance walking as I initially thought.
After wearing them consistently over several consecutive days, I started noticing discomfort around my feet, especially during extended periods of walking. Not unbearable pain, but enough to make me more aware of the boots than I’d like to be during all-day wear.
And honestly, I think that’s important to mention because first impressions and long-term experiences with footwear can sometimes be very different things.
It’s also partly why I now wear them more selectively, usually around twice per month alongside other footwear in my rotation.
That said, I still think they strike a very good balance between comfort, durability, and everyday practicality compared to most Chelsea boots I’ve owned.
I also notice a few more drawbacks such as getting them on and off.
Even with the pull tabs, I still struggled slightly sliding my feet into the boots: something that surprisingly hasn’t completely disappeared till date.
The third drawback was the visible logo placement on the pull tabs and outsoles. I generally prefer footwear with minimal exterior branding.
Their bulkier silhouette also makes them less suited to formal tailoring compared to slimmer Chelsea boots with flatter soles. Even so, I was fully aware of this before buying them, but I still felt it was worth mentioning. Personally, I wouldn’t wear them with formal trousers; however, for casual and smart-casual styling, they work extremely well.
Ultimately, these drawbacks feel relatively minor when weighed against everything the boots get right.
The first thing I noticed after unboxing them was how solid and practical they felt.
The uppers are made from waxed nubuck leather, which gives the boots that slightly rugged, worn-in appearance straight out of the box. Unlike polished smooth leather, which can sometimes feel overly formal or delicate, the waxed nubuck hides creases and marks much more naturally over time. They’re also water-resistant with thinsulate insulation for colder weather.
Living in the UK, where rain is almost unavoidable, those details quickly became genuinely useful rather than just marketing points.
Inside, the boots combine leather and textile lining with a contoured EVA insole designed for shock absorption and everyday comfort.
The elastic side panels also felt firmly stitched, and the boots overall looked built for actual use rather than just appearance.
Compared to many slimmer Chelsea boots, the Blundstones have a slightly chunkier and more rugged silhouette, which naturally makes them lean more casual stylistically, but not in a way that feels limiting or difficult to style. Personally, I found they worked best with jeans, chinos, corduroy trousers, cargos, and other relaxed smart-casual outfits.
Another thing I appreciated was the grip underneath the boots. The rough-textured outsoles handled slippery pavements and wet surfaces surprisingly well.
Testing Phase
As mentioned earlier, comfort was the biggest reason I bought these boots in the first place, so naturally, I decided to test them properly almost immediately.
The day after receiving them, I wore them around Victoria, Oxford Street, and Knightsbridge in London. The goal was simple: test the comfort, test the sizing, and see how they handled colder weather conditions.
The first impression was honestly very positive.
For nearly seven hours, I walked around shopping areas, stood on buses and underground trains, and experienced almost no discomfort whatsoever.
That first-day comfort genuinely impressed me.
Unlike many leather boots that require painful break-in periods, the Blundstones felt supportive and wearable almost immediately. The extra footbeds included in the box also turned out to be unnecessary because the sizing fit me perfectly straight away.
The Thinsulate insulation also helped noticeably given how cold it was that day, making the boots feel warm without becoming overly heavy.
However, my opinion on comfort became more nuanced over time.
While the boots remained excellent for casual everyday wear, commuting, shorter outings, and moderate walking, I eventually realised they weren’t quite as ideal for long-distance walking as I initially thought.
After wearing them consistently over several consecutive days, I started noticing discomfort around my feet, especially during extended periods of walking. Not unbearable pain, but enough to make me more aware of the boots than I’d like to be during all-day wear.
And honestly, I think that’s important to mention because first impressions and long-term experiences with footwear can sometimes be very different things.
It’s also partly why I now wear them more selectively, usually around twice per month alongside other footwear in my rotation.
That said, I still think they strike a very good balance between comfort, durability, and everyday practicality compared to most Chelsea boots I’ve owned.
I also notice a few more drawbacks such as getting them on and off.
Even with the pull tabs, I still struggled slightly sliding my feet into the boots: something that surprisingly hasn’t completely disappeared till date.
The third drawback was the visible logo placement on the pull tabs and outsoles. I generally prefer footwear with minimal exterior branding.
Ultimately, these drawbacks feel relatively minor when weighed against everything the boots get right.
Four years later: how the Blundstone 585 has held up
When I first reviewed these boots on my channel back in 2022, and later published the review here in 2024, my focus was mostly on comfort and first impressions.
Now, however, I think the more interesting conversation is how they’ve actually aged over time and honestly, surprisingly well.
What I appreciate most now isn’t just the comfort anymore, but how naturally they’ve become part of my everyday rotation. They’re the kind of boots I instinctively reach for whenever the weather looks unpredictable or I know I’ll be spending hours outside in colder conditions.
And considering I wear them roughly twice per month, the condition they’re still in honestly says a lot about the quality of the construction.
The waxed nubuck leather has aged beautifully.
Over time, the boots have developed natural creasing, darker tonal variations, softened textures, light scuffing, and visible signs of wear throughout the uppers.
But unlike polished leather that can sometimes look damaged as it ages, the rustic waxed finish actually benefits from wear.
The boots genuinely look better now than when they were brand new.
Structurally, they’ve also held up impressively well.
The stitching still looks clean, the elastic side panels haven’t overstretched, and the overall shape of the boots still feels supportive and structured.
Even the outsoles have aged better than I expected.
After years of walking through London streets, underground stations, buses, rainy pavements, and colder winter conditions, the soles still feel durable with plenty of grip remaining underneath.
That impressive first-day comfort still holds true in many ways, but after years of ownership, I’d describe the boots more as comfortable for everyday wear: commuting, casual outings and city walks, rather than ideal for extremely long-distance walking.
And honestly, I think that’s a fair trade-off considering how durable and supportive they’ve remained overall.
Some of the original drawbacks still remain too.
For instance, getting them on and off can still feel slightly annoying at times despite the pull tabs, especially with thicker socks. And stylistically, the chunkier silhouette still limits how formal they can look.
But as mentioned, all of these complaints feel relatively minor compared to everything the boots get right.
What stands out most after four years is how dependable they’ve been.
They’re not boots I constantly worry about scratching, creasing, or wearing in bad weather.
And I think that’s ultimately the appeal of the Blundstone 585.
They’re not trying to be flashy luxury boots or ultra-fashion-focused Chelsea boots. Instead, they focus on practicality, durability, decent level of comfort, and effortless everyday wearability, and after four years, I’d say they succeed at all four remarkably well.
Final verdict
I still think the Blundstone 585 Rustic Brown are genuinely great boots.
They’re durable, versatile, weather-resistant, comfortable for everyday wear, and ages beautifully over time. More importantly, they feel honest, the kind of footwear you can actually live in without constantly worrying about damaging it.
That said, despite all the great things about them, I probably wouldn’t buy this exact model again.
Not because they’re bad boots, but because my personal style has evolved quite a bit since first buying them.
Over the years, I’ve started leaning more toward slimmer silhouettes and slightly more refined footwear with cleaner, dressier soles. And while I still appreciate the rugged practicality of the 585, I now find myself preferring Chelsea boots that can transition a little more naturally into smarter outfits.
So if I were buying another pair from Blundstone today, I’d probably go for the Blundstone 1306 Dress Boot instead.
The 1306 keeps much of what makes Blundstone great: comfort, durability, versatility, and weather resistance, but packages it in a slightly sleeker chisel-toe silhouette with a more formal-looking sole.
And honestly, I think that perfectly reflects where I currently am in my style journey.
Still, for anyone looking for rugged, dependable Chelsea boots that can genuinely handle everyday life while aging beautifully over time, I honestly think the Blundstone 585 remains one of the best options out there.
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