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10 best chunky boots for women this winter - go big or go home

Pound the pavement in a pair of tough chunky boots…


best chunky boots
Leanne Bayley
Director of Lifestyle & Commerce
Updated: October 30, 2023
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Toughen up your new season style with a pair of chunky boots. Whether you're after a pair of M&S chunky biker boots or a pair of zip-up boots from The Row, it's all about stomping into the new season so loudly that everyone can hear you coming a mile off. 

The chunky boot trend has been around for some time now - so if you're looking to go the extra mile for a little more thud, you know what to do. Keep on reading!

Best chunky boots for women - at a glance

Luxury chunky boots: It has to be the zip-up style from The Row.

Affordable chunky boots: John Lewis has come through with an incredible lookalike of the above

Best mid-priced chunky boots: Russell & Bromley's chunky boots are spot-on! 

Waterproof chunky boots: Opt for Merry People or UGG.

Celebrities wearing chunky boots

Celebs love their chunky boots, too! Everyone from Olivia Palermo to Kendall Jenner rocks their chunky heavy-soled boots. See how they scroll them, and scroll down to get expert pointers from fashion stylist Holly Coopey…

celebrities wearing chunky black boots© Shutterstock
From left to right: Olivia Palermo, Hailey Bieber, Rosie Huntington-Whiteley and Kendall Jenner

How we chose the best chunky boots for women

  • Style: These boots have one thing in common - they're chunky with thick soles. 
  • Availability: At this time of year, sales soar for chunky boots at this time of year, so the editor who has edited this list wanted to ensure all boots were in stock at the time of publishing. 
  • Hard wearing: While a lot of these boots are for fashion purposes - we wanted to ensure we included weather-proof options. 
  • The Row chunky boots we love

    The Row chunky black boots

    The Row Leather Ankle Boots

    The Row's versatile, combat-inspired boots have been a huge trend in recent years and the trend shows no sign of waning. You can wear these with everything from tailoring to maxi dresses. Distinctive thanks to the front zipper, these boots have been made in Italy from supple black leather and are set on a chunky rubber sole.

    The boots are such a popular design that lookalikes have swept the high street, and there may even be a pair of two within this edit that are a bit more affordable. 

  • Marks & Spencer chunky boots we love

    Marks and Spencer chunky boots

    M&S Collection Chunky Buckle Flatform Ankle Boots

    You can always trust Marks & Spencer to bring out an excellent pair of chunky boots at a not-so-chunky price tag. These ankle boots look great and feel good, too, thanks to their flatform sole and mid-height heel. What's more, these boots feature Insolia Flex, M&S's technology that improves the movement of the balls of your feet, which are positioned correctly to ensure greater comfort for longer. 


    Design wise, there's a side zip, buckles and laces which mean they always fasten securely. 

  • John Lewis chunky boots we love

    John Lewis chunky boots The Row dupes

    John Lewis Purdie Ankle Boots With Front Zip

    See! We told you we found a pair of affordable front zip boots! These Purdie ankle boots from ANYDAY are defined by the silver front zip fastening, which is set onto an exaggerated chunky cleated sole to give a subtle lift.

    Crafted from leather, these are great quality and are finished with an inside zip for ease of entry.

  • Merry People chunky boots we love

    Merry People boots

    Merry People The Tully Boot In Black

    This is a bit of a rogue choice for this edit, but this isn't just any chunky boot - it's a chunky wellington boot! Merry People is a brand we've recently come across, and The Tully Boot is a brand new silhouette that gives a fashion forward take on the classic ankle wellie!

    The Tully nods to 90s nostalgia with a chunky platform-style sole and an extended, wrap around neoprene cuff. The boots are 100% vegan, and made from 85% recycled PU and the platform sole is made from 20% recycled rubber.

    If black isn't for you, you can also get three other colour-combos; Teal, Sunshine, and Plum. 

  • Russell & Bromley chunky boots we love

    Russell & Bromley chunky boots we love

    Russell & Bromley The Rebel Boot

    Russell & Bromley is a firm favourite here at HELLO! The Rebel boot is a must-have for the new season, The laceless zip-front boot has been handcrafted in Italy from black calf leather, and made to look like a classic lace-up ankle boot - but sans laces. The boots are fully leather lined and feature a grooved rubber sole, with a zip front fastening and pewter-hued hardware.

  • Grenson chunky boots we love

    Grenson boots

    Grenson Carina Boots

    The Grenson Nanette was a boot that was so popular, and if you still own a pair, they still look great. But we wanted to see what's new and exciting at Grenson and we came across the Carina boot, which is a captoe chelsea boot made from black calf  leather with a rubberised leather bumper. So simple but so stylish! The boots are made with a sand coloured lightweight commando sole.

  • Dr. Martens chunky boots we love

    Dr Martens boots© Dr Martens (Airwair Internationa

    Dr. Martens Jaden || Boot

    The OGs of the chunky boot trend! Dr. Martens is synonymous with the chunky boot aesthetic so of course we wanted to include a pair of Docs in this edit. This reworked version of the Jadon boot is fitted with a padded collar and futuristic shiny oval-shaped hardware. Built from supple Buttero leather, the boot stands on a quad sole for unmissable height.

  • Bottega Veneta chunky boots we love

    Bottega Veneta boots

    Bottega Veneta Chunky Black Boots

    Ok, so if your budget is more in line with Molly Mae's budget, these Bottega Veneta chunky boots are absolutely gorgeous and a more modern take on the older - bestselling - Bottega style. 

    With the round toe and the gold-toned Morsetto horsebit hardware, these chunky boots look so polished and almost regal. 

  • UGG chunky black boots

    UGG Women's Droplet Mid Boot

    The UGG boots we've chosen for this edit are very practical indeed! The waterproof Droplet midi boots are waterproof and feature a longer shaft for more wet-weather defence. Thanks to the brand's innovative UGGplush upcycled wool blend, they're nice and cosy inside, too!

  • H&M chunky boots we love

    h&m chunky boots

    H&M Chunky Lace Up Boots

    If you used to love the Grenson hiker boots - which are still available by the way - you might be interested in this pair of ankle boots from H&M. The affordable style has been coated, and inside you'll find soft teddy lining on the tongue. 

How to style chunky boots

Fashion stylist Holly Coopey is a big fan, and told us: “A pair of chunky boots will be your best friend once you give them a try. I couldn’t be without mine!”

Styling wise, Holly says it’s easy: “A pair of black chunky boots works really well worn with jeans and a jumper, or an oversized blazer. If they’re black, try and link up with a black crossbody bag or a big chunky scarf. I love styling my black chunky boots with midi length dresses and tights, throwing over my trusty leather jacket over the top.”

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How to clean black leather boots

Wipe away dirt using a damp cloth. Apply a neutral or correct coloured wax based shoe polish. Use a soft cloth to apply and allow the polish to dry so the leather can absorb it properly. Then buff away any excess polish with a cloth or brush.

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