19 Pairs Of Chelsea Boots To Take You Through The Seasons

Platforms, chunky heels, lug soles, boots with (faux) fur – and even a pair made from plastic bottles.
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<a href="https://www.amazon.com/Steve-Madden-Womens-Howler-Fashion/dp/B09QH9V2KH?th=1&tag=griffinwynne-20&ascsubtag=63209d6ce4b0eac9f4db9ab5%2C-1%2C-1%2Cd%2C0%2C0%2Chp-fil-am%3D0%2C0%3A0%2C0%2C0%2C0" target="_blank" role="link" data-amazon-link="true" rel="sponsored" class=" js-entry-link cet-external-link" data-vars-item-name="Platform heeled boot" data-vars-item-type="text" data-vars-unit-name="63209d6ce4b0eac9f4db9ab5" data-vars-unit-type="buzz_body" data-vars-target-content-id="https://www.amazon.com/Steve-Madden-Womens-Howler-Fashion/dp/B09QH9V2KH?th=1&tag=griffinwynne-20&ascsubtag=63209d6ce4b0eac9f4db9ab5%2C-1%2C-1%2Cd%2C0%2C0%2Chp-fil-am%3D0%2C0%3A0%2C0%2C0%2C0" data-vars-target-content-type="url" data-vars-type="web_external_link" data-vars-subunit-name="article_body" data-vars-subunit-type="component" data-vars-position-in-subunit="0">Platform heeled boot</a>, <a href="https://www.amazon.com/Kenneth-Cole-REACTION-Womens-Chelsea/dp/B07T6NN5NG?tag=griffinwynne-20&ascsubtag=63209d6ce4b0eac9f4db9ab5%2C-1%2C-1%2Cd%2C0%2C0%2Chp-fil-am%3D0%2C0%3A0%2C0%2C0%2C0" target="_blank" role="link" data-amazon-link="true" rel="sponsored" class=" js-entry-link cet-external-link" data-vars-item-name="Chelsea boots" data-vars-item-type="text" data-vars-unit-name="63209d6ce4b0eac9f4db9ab5" data-vars-unit-type="buzz_body" data-vars-target-content-id="https://www.amazon.com/Kenneth-Cole-REACTION-Womens-Chelsea/dp/B07T6NN5NG?tag=griffinwynne-20&ascsubtag=63209d6ce4b0eac9f4db9ab5%2C-1%2C-1%2Cd%2C0%2C0%2Chp-fil-am%3D0%2C0%3A0%2C0%2C0%2C0" data-vars-target-content-type="url" data-vars-type="web_external_link" data-vars-subunit-name="article_body" data-vars-subunit-type="component" data-vars-position-in-subunit="1">Chelsea boots</a>, <a href="https://www.amazon.com/dp/B098L7QG18/ref=twister_B079MSN9X3?tag=griffinwynne-20&ascsubtag=63209d6ce4b0eac9f4db9ab5%2C-1%2C-1%2Cd%2C0%2C0%2Chp-fil-am%3D0%2C0%3A0%2C0%2C0%2C0" target="_blank" role="link" data-amazon-link="true" rel="sponsored" class=" js-entry-link cet-external-link" data-vars-item-name="faux fur boots" data-vars-item-type="text" data-vars-unit-name="63209d6ce4b0eac9f4db9ab5" data-vars-unit-type="buzz_body" data-vars-target-content-id="https://www.amazon.com/dp/B098L7QG18/ref=twister_B079MSN9X3?tag=griffinwynne-20&ascsubtag=63209d6ce4b0eac9f4db9ab5%2C-1%2C-1%2Cd%2C0%2C0%2Chp-fil-am%3D0%2C0%3A0%2C0%2C0%2C0" data-vars-target-content-type="url" data-vars-type="web_external_link" data-vars-subunit-name="article_body" data-vars-subunit-type="component" data-vars-position-in-subunit="2">faux fur boots</a>.

Popular items from this list:

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1
A pair of leather Kenneth Cole Reaction Chelsea boots to tuck your skinny jeans
Promising review: "They’re soft, they’re the perfect heel height for my comfort, and I’ve walked all day, multiple days – with no pain or regret afterwards. As someone who usually never buys shoes online because of pickiness and my sometimes up-sizing, I’m happy I took the chance with these." — Katherine Jordan
2
Amazon
A nonslip pair of chunky platform Chelsea boots
Promising review: "These look like real leather and like the ones I ALMOST bought from Zara last year but for half that price. They are so so comfy although I have really bad feet….I can wear these for hours and hours and I also love the height of the boots, which looks fantastic with midi dresses, with an oversize shirt and bike shorts, just about every outfit I can think of. And they look like real leather (oh did I already say this?)." – DLS Jones
3
A highly rated pair of stylish Asgard Chelsea rain boots
Promising review: "I loooove these boots! They fit as expected (if not a little better) and are very comfortable to wear all day. I was completely amazed by how cute and comfortable they are! Not to mention, they go well with anything you wear! I wore these with jeans on Tuesday and on Wednesday I wore with a sweater dress." — Myra G
4
A Thursday Boot Company "Duchess" Chelsea boot crafted from genuine leather
Note: Some reviewers suggest ordering half a size up.

Promising review: "They fit great! The leather is beautiful. They smell really good. They look very suave and debonair. I’m sitting on the sofa watching TV because I don’t want to take them off. They were not too narrow and fit comfortably. They also were not too long. I ordered the leather not the suede. They are the look that I was going for. A dressier look than my normal work boots that I bum around in. I’m very happy with these classy boots!" — CMaxDavis
5
A pair of slip-resistant leather Dr. Martens platform Chelsea boots lined with cozy faux fur
Promising review: "I found out I had to spend two weeks in Europe during the winter and ordered these in a pinch. Best. Decision. Ever! They are comfortable, warm, and weatherproof. They survived the snow, ice, and rain. They are also very easy to dress up and down." — Mari
6
Free People
An "essential" pair of Free People boots featuring a stacked heel and Spanish-made leather
Note: Some reviewers say these run narrow.

Promising review: "I love these boots! They are comfy and can be worn for hours if you get the right size. Love the neutral color and the wooden heel. The zip on the back is perfect – it doesn’t rub your calf/ankle uncomfortably. A must buy!" — Idrin
7
Michael Kors
Some edgy leather Michael Kors Chelsea boots anyone who loves little twists on classic looks would appreciate
Promising review: "I love these boots. They're comfortable and there's no need to break them in." — Joqueta
8
Everlane
A gorgeous pair of Everlane Chelsea boots made of luxe nappa leather from Florence, Italy
Promising review: "Fabulous leather, fit, and details straight out of the box. No break in; just perfection and the price can’t be beat. Second pair of Everlane boots and it’s all love. Ordered my usual size – great toe box and ankle fit." —Dr Janet

Another promising review: "I love, LOVE these boots! I wear them almost every day in almost all types of weather and they still hold up." — Kombas
9
Torrid
A faux leather Torrid platform bootie that'll win your heart over the second you slide your feet into 'em
Promising review: "These boots are perfect. The style and fit are exactly what I had hoped for. They are also extremely comfortable. If you want a great looking chunky boot these are for you. I am so glad I got these. You will not be disappointed." — Snickers123
10
Nisolo
Some sleek Nisolo leather Chelsea boots best worn with some comfy jeans or a cute midi dress
Note: These run half a size small.

Promising review: "These boots are absolutely beautiful. These are without a doubt the nicest pair of shoes I own. Definitely go up a half size! I usually do this for boots anyway, but these are a bit snug. A whole size up would be too roomy. BUY THESE! You won’t regret it, and I’m sure these will last forever with proper care! I bought a pair in black too because I know these are the real deal." — Rebecca M.
11
A pair of Steve Madden Chelsea booties with a lil' platform
Bonus points for you being able to wear these year-round!

Promising review: "Obsessed with these boots!!! I went hiking in them, walked in the Ireland rain and puddles! They are comfortable and great for terrain!!! I got so many compliments on them as well! You must buy these!!!" — Sata
12
DSW
A durable pair of Timberland Chelsea boots
Promising review: "I bought these boots to have a pair of sturdy shoes for a trip to Idaho. These were beyond my expectations. Cute, comfy, and true to size. I wore these for six days straight. Upon coming home, I have worn them repeatedly with jeans and leggings. I am planning on wearing them with a flowy maxi skirt next week. So, so, so cute! I highly recommend! Worth every penny!" — Lisadee
13
Frye
A pair of sleek full-grain leather Frye booties
I also may or may not have just purchased a pair of these myself.

Promising review: "LOVE, LOVE, LOVE these booties. I can't say enough about this purchase...so comfortable and conforming to the foot. Pure quality. I feel so classy wearing these! I will definitely be back!!!" — Goozgirl
14
A fully waterproof leather Sorel Chelsea boot designed to take on the elements with ease
Promising review: "These shoes are amazing! I bought them for a trip to Paris because it was going to be rainy when I was there and they did not disappoint. They were warm and waterproof, but most importantly, they were comfortable! I walked 24 miles in these shoes over three days with absolutely no issues. Now that I'm back from my trip, I wear them almost daily as causal boots with jeans. I love them! I would HIGHLY recommend these." — Jenny D
15
A machine-washable Rothy's Chelsea boot knit from plastic bottles
Promising review: "Genuinely one of my favorite shoes of all time! I've been wearing them on casual days in the office for years and they've still held up without looking shape at all. Super comfortable and I can wear them all day. They seem extremely simple but something about the ankle boot look just gives it some pop unlike a regular sneaker would. Allows me to still wear socks. True to size even with socks." — EMMY
16
Zappos
A trusty pair of Ugg "Markstrum" boots featuring waterproof leather uppers that are built to last
Promising review: "I absolutely love these boots. They are true to size. Not too narrow or tight. They are super comfortable – even the first time I wore them. I have a hard time finding shoes that are comfortable to me and Uggs never disappoints. These boots will go with many different outfits. I love the chunky heel and think it gives it a little edge to my outfits when dressing up." — Jen B
17
Hunter
A darling pair of Hunter rain boots handcrafted from natural rubber
Promising review: "The rubber that covers the inside of the fabric is an excellent design feature so that feet are protected! I love the ease of wearing them...great for unpredictable weather!" — MillyP
18
Free People
A pair of Free People leather Chelsea boots showcasing a chunky heel
Promising review: "LOVE. Amazing quality, the color is an exact match to online, and the block heel is so easy to walk in. They legit go with everything, I am traveling next week and they’re my airport boots!" — Jessranks
19
Bloomingdale's
And a splurge-worthy leather Stuart Weitzman platform Chelsea boot you'll be able to wear year after year
Note: Some reviewers suggest ordering half a size down.

Promising review: "These are the most comfortable boots. I know that I’ll wear them to death. I feel super cool wearing these very stylish platform Chelsea boots." — West sider

Get them from Bloomingdale's for $550 (available in sizes 5–11 and two colors).

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