There’s a particular kind of betrayal that only footwear can deliver.
It’s the moment you realise that your gorgeous new boots – you know, the ones you smugly declared “surprisingly comfy” in the mirror that morning – have conspired against you by lunchtime.
One minute you’re striding along with purpose and agency; the next you’re limping into the nearest café in your lunch hour, searching for a chemist on the way to stock up on blister plasters.
Heels are supposed to be empowering. They’re supposed to signal to passers-by and co-workers that you’ve got places to be, emails to send, and possibly a negroni with your name on it. But anyone who’s tried to navigate a full day of London pavements, stairs, and unpredictable weather in a pair of stilettos knows the reality can feel more like an obstacle course.
The good news? You don’t have to choose between chic and sheer survival anymore. It’s impossible to know whether the chunky heel on those knee-highs you’ve been eyeing for some time now will actually prove comfortable with extended wear. That’s why I’ve road-tested a selection of top picks for your purchasing pleasure.
Why you should trust me
With a lifetime of living in London under my belt, and a few years during my sixth form days when you wouldn’t dare catch me sans Vagabond heeled ankle boots, I’ve done my fair share of rigorous testing. Think block heels that don’t wobble on cobblestones, cushioned insoles that feel luxurious, and silhouettes that look just as sharp at a job interview as they do at the bar afterwards.
Consider this your shortcut to styles that deliver both polish and stamina. Remember, great boots are an investment in premium design and quality. They won’t come cheap, but they’ll last you a lifetime. Ready to meet the heeled boots that won’t make you regret every step?
Lace up (or zip up) and let’s begin.
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Vagabond Meryl Boots
A classic, understated ankle boot that does the heavy lifting for your wardrobe.
The smooth leather and block heel give them just enough polish for office wear while still being versatile enough to throw on with jeans at the weekend. Vagabond’s knack for balance – between height, comfort, and that minimalist Scandi aesthetic – means these will quickly become the pair you reach for without thinking.
A shoemaker known for epitomising style and comfort, you simply can’t go wrong with their frequently sub-£200 kicks.
Buy now £165.00, Vagabond
Miista Cass Brown Patent Boots
I first bought into Miista’s coveted E8 range back in 2020 and have been a firm fan of the shoemaker ever since.
Aside from one faulty pair, which was duly replaced by the brand with a voucher surpassing their value for my troubles (pre-journalism days), my Miista boots have never failed me. Expertly made and undeniably comfortable, these are my current favourites from their heeled boot range – the Cass Brown Patent Boots.
They’re striking with their 60s-inspired silhouette, and I love the signature mid-calf length with the chunky 6cm block heel. They even come with a replacement pair of heel caps when they inevitably require a trip to the cobbler after frequent wear and tear. Do bear in mind that they’re not waterproof, so don’t go jumping into any puddles.
For a more weather-resistant pair, opt for ones without a patent finish, like these Malene boots.
Buy now £370.00, Miista
Camper Nikki Boot
Camper recently experienced a viral moment on TikTok when an NYC-based creator ranked her most comfortable summer sandals for the city. Let me introduce you to said viral shoe’s winter counterpart: the often sold-out Nikki boot.
Featuring comfortable Ortho-Lite footbeds, the sculptural silhouette of this boot – with its cylindrical heel and ultra-supple finish – immediately evokes an editorial feel. Designed to elevate every outfit with ease while taking you from A to B with cloudlike comfort, grab yours in your favourite hue before they’re all gone.
Buy now £208.85, Amazon
Duo Boots Dalia Tall Knee High Boots in Black Croc
British heritage brand Duo Boots are celebrated for their inclusive sizing, offering multiple calf widths across their collections, and the Dalia knee-high is one of their most striking styles.
Made from premium croc-embossed leather, the boot balances a sleek, 70s-inspired tall shaft with a sturdy 7cm block heel that’s practical for every day. A full side zip ensures easy on-and-off, while the almond toe keeps things timeless.
Pair with everything from midi skirts to skinny trousers and prepare for compliments.
Buy now £295.00, Duo Boots
Bobbies Mona Boots
Founded in Paris, Bobbies have built a cult following for their handcrafted shoes made in Portugal, and the Mona boot encapsulates that commitment to detail.
This pair comes in supple Irish Coffee leather with a chic 6cm block heel and a slightly tapered ankle that makes them endlessly flattering. The leather lining and insole mean they’ll mould beautifully to your foot, and I love the warm tone which pairs as easily with neutrals as it does jewel colours.
They’re boots with true Parisian polish, minus the pretension.
Buy now £270.00, Bobbies
Saint + Sofia Kansas Western Boot
Saint + Sofia design everything in London before handcrafting in Portugal, so the Kansas Western boot embodies the best of both worlds: edgy city styling with artisanal quality. Made from soft Nappa leather with a pointed toe, Cuban heel and subtle western stitching, it nods to cowboy heritage without veering into fancy-dress.
The smaller heel height is walkable all day, and the elasticated side panels mean you can slip them on and off between meetings. I hardly took these off during a long weekend in Paris, and my feet didn’t suffer once.
Small warning, though: the insole is bright red and will rub off on your favourite white socks, so stick to darker colours.
Buy now £359.00, Saint + Sofia
Anonymous Copenhagen Jasmina 50 Leather Stiletto Calf Boots
Copenhagen label Anonymous specialise in sustainable, small-batch footwear, and the Jasmina is a masterclass in understated Scandi glamour. Handmade in Portugal from LWG-certified leather, the boot’s calf-length silhouette and slim 5cm stiletto heel offer elegance without compromising walkability. They also feature a specially developed crepeline outsole brilliant wear resistance.
A pointed toe elongates the leg, while the side zip ensures a sleek fit against the ankle. It’s a polished, quietly luxurious boot that’s perfect for those who don’t love the look of a chunky block heel.
Plus, I love the versatility offered by the supple leather – scrunch the boot down for effortless vintage-inspired folds or pull them up for a sleeker look.
Buy now £270.00, John Lewis
Jonak Paris Betina Calf Boots in Distressed Leather with Heel
Jonak has been a Parisian staple since the 1960s, known for blending contemporary trends with enduring craftsmanship. The Betina boots are cut from distressed brown leather that softens beautifully with wear, set on a 7cm stacked block heel that adds height without sacrificing comfort.
The mid-calf shaft makes them surprisingly versatile; easy to tuck slim trousers into, but equally good with skirts. The rounded almond toe and inside zip give them a practical edge, while the weathered finish ensures they look like an old favourite from the very first outing.
Get ready to Jane Birkin-ify every outfit.
Buy now £249.99, La Redoute
