As I’m sure you have already noticed, it’s started to get a little chilly outside. And by a little, I mean a lot.
But winter is one of the best times to start experimenting with layering and cosy (yet chic) outfits that you can easily rotate through the week.
And the most essential layer of all? Boots.
Not just any boots, but comfortable ones. Ones you can wear all day and won’t have you a blistered mess by sunset.
And because the only way to know if something is worth buying is through personal recommendations, I asked the WHO team to tell me their most comfortable boots they’re wearing for winter.
The most comfortable winter boots, according to our editors
Jo Mercer boots
Lyndsey, Editor: “I bought these Jo Mercer Chelsea boots last year and, not going to lie, they did take some breaking in! However, they are now my favourite boots and so unbelievably comfy.”
“I am not a fan of looking too feminine, so I love pairing these with dresses and skirts and softer pieces to edge them out a little.”
The exact boots are (sadly) no longer available to buy, but Lyndsey has found similar alternatives that should be just as good.
Harper Flat Ankle Boots
$279.95
Dorian Flat Ankle Boots
$299.95
Tatum Flat Ankle Boots
$329.95
Billini boots
Chanelle, Shopping Editor: “As soon as the temperature starts to drop, I bring my all-time favourite boots back into rotation.”
“Not only are they unbelievably easy to style, but they’re actually comfortable and don’t hurt my feet after 12+ hours of wear.
“They even lasted me from day to night during Fashion Week. I have the featured pic as proof!”
Caston Boots
$139.95
Billini boots (again)
Madison, Senior Content Producer: “Some might say I was heavily inspired by Caroyln Bessette-Kennedy in Love Story (I was), but these chic, square-toed boots are my go-to this winter.”
“More refined than a round toe and more comfortable than a pointy toe, this pair from Billini screams 90s and can take me from day to night without blisters (a non-negotiable).”
Alania Boots
$109.95
Why trust WHO Shopping?
WHO has been covering celebrity culture, red carpet moments and entertainment news for decades. Our shopping team works alongside our entertainment editors to identify the exact products behind the looks everyone’s talking about, from awards season glam to off-duty essentials.
We regularly consult stylists, makeup artists, trainers and industry insiders to verify product details and understand why these items perform under real-world conditions. When we recommend something, it’s because it’s genuinely relevant to the moment, not just trending.
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