17 Chunky Chelsea Boots You Need This Fall

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Chunky chelsea boots have been around forever. Years ago they were mostly seen paired with edgier, grunge style outfits but today you’ll see them styled so many different ways.


I was never huge into the chelsea boot style until comfort started becoming more important to me (hello motherhood). While I love to be stylish I’ve grown past the days of believing that beauty is pain.


chunky chelsea boots


You can still wear a great outfit and be comfortable and the chunky chelsea boots below prove that! Whether you’re wearing jeans and a tee, a floral dress, or leggings & an oversized sweater – chunky chelsea boots can complete the look.


The Best Chunky Chelsea Boots


chunky chelsea boots


#1.) Steve Madden Howler

These boots are hands down one of my favorite purchases from all of 2020. They are SO incredibly comfortable, the color is absolutely gorgeous, and they aren’t too heavy. They do come in other colors but I just love this neutral tan.

Fit: True to size



#2.) Sam Edelman Darielle

Wondering how you can wear your boots in the warmer months? Try a white pair with your favorite cutoff shorts or a floral maxi dress!



#3.) Robbie Chunky Chelsea Boots

With a mid-block heel and easy pull-on tab, this black pair is more of the “classic” chelsea boot. They feature elasticized inserts, a moulded grip tread, and they’re only $43!


black chunky chelsea boots with stud detailing


#4.) Amulet Chelsea Boots

Another one of my all-time favorite boot purchases. These lug sole chelsea boots are like walking on a cloud! The stud detail around the ankle is the perfect added touch but if you aren’t a fan of the look you can remove it. These are very comfortable, fit true to size, and pair perfectly with leggings.



#5.) Platform Chelsea Boots

Looking for an edgier pair of boots? Or….maybe you just need some extra height? lol Check out this platform pair that clocks in at only $33.



#6.) Cadence Brown Abruzzo Leather Chelsea Boots

Surprise, surprise, another pair of Doc’s made the list! This pair definitely leans toward a more preppy/classic style and can easily be paired with a plaid button-down or tweed mini skirt.



#7.) James Chelsea Boots

I’ve had my eyes on these boots since last year and just haven’t brought myself to splurge yet lol. They are so chic and would pair perfectly with a boho/vintage outfit. This color would work well in any season  (though they do come in 4 other equally amazing colors) and the 4″ shaft sets them apart from most other chunky chelsea boots.



#8.) Lamoda Lug Sole Chelsea Boots

Another great classic option is the all-black Lamoda. Features include easy pull-on tabs, a lugged tread, elasticized inserts, and a round toe. At $70 these are definitely a more affordable option than the ever-so-popular Doc Marten’sbut just as easy to style.



#9.) Irby Chunky Chelsea Boot

Priced at just under $60 is the Coolway Irby Chelsea Boot. Available in dark brown faux suede or black faux leather this is another pair with a more classic style. Reviewers note that they aren’t heavy and they are comfortable enough to wear all day.



#10.) Spence Leather Flared Heel Chelsea Boots

Doc Marten’s just might be the leader when it comes to boots as a whole. Docs are known for high quality and a very distinct style, no matter what boot you choose. However, they’re also known for their hefty price tag. This Spence Flared Heel style comes in at $160.



#11.) Dolce Vita Arlete

Here’s another casual/preppy pair of chelsea boots. These aren’t “chunky” per se but do have the thicker sole and chelsea style structure. They are available in tan suede, gray suede, and black nubuck.



#12.) Dolce Vita Huey

If you love the chelsea boot style but want a little more detail, check out this #1 best-selling boot! I absolutely love the croc print and timeless design of these. If you aren’t into the croc print there are 8 other colors (prints and solids) to choose from.


black chunky chelsea boots


#13.) Steve Madden Chunky Chelsee Bootie

With a round, closed-toe and tread bottom sole these boots are comfortable and stylish. Side goring allows for an easy pull-on style and the price is one of the most affordable on the list.


tan chunky chelsea boots

brown chunky chelsea boots



#14.) Lug Sole Platform Chunky Chelsea Boots (waterproof!)

LOVE THESE!!! These lug sole chelsea boots would be perfect for the summer to fall transition. They come in suede varieties as well as waterproof options, 13 colors, AND they’re under $50!!! Throw these on with a floral dress or mini skirt and you’ve got the perfect girly yet edgy outfit.



#15.) Waterproof Chelsea Rain Boots

Looking for a pair of stylish chunky chelsea boots that also double as rain boots? Look no further. This pair by Sorel is made with waterproof leather and a rubber sole making them great for rainy days. Sorel is known for its high-quality products and these chic boots are no exception.




#16.) Laguna Chelsea Boot

These boots are just gorgeous! They are made of 100% leather and come in 4 colors and have an easy slip-on style. With a slightly squared-off toe these boots are trendy yet sleek and are perfect for transitioning from fall to winter.



#17.) Courmayeur Valley Chelsea Boots

If rugged/woodsy chunky heel chelsea boots are more your style these are definitely worth checking out. Timberland is another brand that’s been around forever and is known for its high quality products. These boots are available in 8 colors and have rave reviews on Amazon.


That’s it for this list of chunky chelsea boots! If you have a pair that you love that didn’t make the list be sure to drop a comment below so I can add it in!


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Lauren is a wife, mom of 3, and personal trainer with a passion for fitness, fashion, and blogging. She shares affordable fashion finds, fitness tips, and helps you learn how to make money with YOUR blog!

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