Original Chelsea Boots

Step into timeless style with our collection of original Chelsea boots. Designed for both comfort and durability, these classic ankle boots feature elastic side panels for easy on-and-off wear. Crafted from high-quality materials, they offer a sleek silhouette that pairs perfectly with any outfit, from casual to dressy. Ideal for year-round wear, original Chelsea boots provide excellent support and traction, making them a versatile addition to your footwear collection. Elevate your look with these essential boots that blend fashion and functionality effortlessly.

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14 products
View:  All|14 Products
HUNTER Women's Original Chelsea Boots
  • Black
  • Sand

HUNTER Women's Original Chelsea Boots

$149.99-$154.99

Quick Facts

nylon pull tab for easy foot entry handcrafted from fsc®- certified natural rubber and vulcanized for superior protection features elasticated- gussets 100%

UGG Men's Neumel Chelsea Boot
  • Mustard Seed

UGG Men's Neumel Chelsea Boot

$139.99

Quick Facts

He loves that shoes. It's not heavy also very comfortable. ... They are comfortable and stylish. ... Fit and comfort are 5 stars per usual. ... Unbelievably

Dr. Martens Men's 2976 Nappa Leather Chelsea Boots
  • Black

Dr. Martens Men's 2976 Nappa Leather Chelsea Boots

$169.99

(7)

Buy them and you can be cool too! ... I finally look cool ... I bought these shoes and am finally cool! ... apply neutral or correct colored wax- based shoe polish and buff with dr. martens shoe brush to restore

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5 Mango
Just right size for me, looking good! Keep wear it to work

5 Chrissy Mayne
Comfy and great shape, the leather is softer than other Dr Martens.

5 ChrisS
Having been a life- long Doc wearer I found these to be very comfortable. Minimal breaking in( at least for me). If you wear thick socks so for a half size larger, otherwise normal and sports socks may feel a little tight when you first put the boots on but losses up when breaking in.

5 Elizabeth
Classic, Comfortable, fashionable and affordable The only boot I buy.

5 Jphn
It's just what the Doctor Ordered................ Nothing more nothing less.

Dr. Martens Women's 2976 Leonore Farrier Leather Chelsea Boots
  • Black Burnished Wyoming

Dr. Martens Women's 2976 Leonore Farrier Leather Chelsea Boots

$179.99

(32)

Cozy with lining. ... Comfortable right out of the box. ... Warm cozy comfortable ... Really Comfortable ... Very comfortable. ... They were very comfortable from the start. ... Comfortable and

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5 Candygrl
Absolutely love these boots! Perfect for NYC ’s snowy weather

5 Dandthecrew
Love these boots! They keep my feet warm while being a little edgy and stylish. I ’ m a 5. 5 to 6 in shoes and the 6 fit perfectly with some room for socks.

5 Jschneider
Purchased about a month ago. They are Comfortable, stylish, and warm! Definitely would purchase them again or in another color.

5 Sheila11
I struggled with whether to buy the 6 or 7. I 'm a true 6- 6. 5. I ended up with the 6 and after a little break in, it was definitely the right decision. Very comfortable and warm enough to wear for recess duty for Michigan winter. Bought the brown color and get tons of compliments. My new favorite.

5 LikesDrMartin
Great pair of shoes! I would recommend them! A little heavy but sturdy.

SOREL Men's Carson Chelsea Boots
  • Camel

SOREL Men's Carson Chelsea Boots

$154.99

(14)

Comfy and good looking. ... They are not insulated, so don ’ t expect a go to winter boot for long days outside, but great for slushy days and the office. ... The fit is right on so if you plan to wear heavier socks you might want to go up 1/2 a size but I 'd rather them be tighter so going my size...

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5 MDB
Great! Thanks, great product. Would definitely recommend this boot and I ’ d order again if they had my size in different colors…………………..

5 Bjunior
Comfortable and well fitted not too loose or tight. It ’s also great for all seasons.

5 Randy D.
Bought these for just everyday boots and absolutely love them. Really no break in time at all and are light on my feet. Great for doing chores around the place to going out to dinner.

5
I wear these shoes to work every day and everywhere. Tough as nails and looks great even beat up. I never complain about foot pain anymore with these. The soles are so tough and the wear is minimal. The leather does wear out after a while meaning a looser fit but the hide hold up. I 'm on my 3 or 4th pair.

5 Michigan guy
I like these boots. They are comfortable- I have a wide foot and a high arch; these boots have a wide toe box and a good footbed. No walking fatigue or foot discomfort. They are not insulated, so don ’ t expect a go to winter boot for long days outside, but great for slushy days and the office. 4 months in I see no quality issues, no water intrusion- granted I have not fully submersed them in water, but no problems for daily Michigan winter use. FYI, I sized up to 11, usually a 10. 5 in length, but most footwear is a touch narrow for me-

Timberland Women's Greyfield Mid Chelsea Boots
  • Black

Timberland Women's Greyfield Mid Chelsea Boots

$119.99

(31)

I ordered two sizes just in case and the return process on the second pair was simple and easy. ... Very well made and is a very comfortable work boot that looks

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5 gabi
Just got these and I love them already, was actually looking to buy another pair but my size is sold out:( please do n't retire them!!

5 Zoe
[# sweepstakes Rather wide toe box for shoes of regular width! A really comfortable pair and elevates your height unnoticeably... I will definitely purchase again when this pair wears out^^ 100/100

5 Lauren
[ This shoe surprised me with how light the sole was. It looks chunky but thankfully does n't seem heavy when walking in it.

5 Diana
[ I 've received so many compliments on this boot. It's easy to wear with so many different outfits and comfortable for long days in the city!

5 Briana
[ I really like these shoes! They 're super cute, but definitely needed to be broken in. Got blisters on my heels the first couple of times, but after a couple of wears, no more blisters! Maybe size up?

Merrell Moab Adventure 3 Chelsea Waterproof Boots
  • Crisp
  • Black
  • Earth

Merrell Moab Adventure 3 Chelsea Waterproof Boots

$159.99-$169.99

(22)

waterproof membrane seals out water and lets moisture escape full grain leather upper double stretch gore for easy on and off 100% recycled mesh footbed cover& microfiber lining cleansport nxt™ treated for natural odor control removable pu footbed merrell air cushion in the heel absorbs shock and...

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5 Brandy
Best boot we ever bought. Sturdy, waterproof and lightweight. Wear them as dress or to work. Clean up easily.

5 Johnny 4
I received these 2 days ago perfect right out the box. I am a corrections officer I wear these on duty and no break in required perfect from the get go as are all my merrells

5 Rick Merrell
Alway wear Merrell ’s a little expensive but highest quality

5 Esn87
Fits like a glove. Finally a boot that comes in “ wide ” sizes. Comfortable and grips well.

5 Sparky
Nice boot! Wore these after a recent snowstorm and they performed great! Kept my feet dry and good traction too.

Timberland Women's Roxie Lane Mid Chelsea Boot
  • Beige
  • Black

Timberland Women's Roxie Lane Mid Chelsea Boot

$140.00

Quick Facts

an easy- on, easy- off style designed for total comfort and versatility. ... the roxie lane chelsea boot gives the classic silhouette a modern edge that ’s ready for every urban

SOREL Women's Hi-Line Heel Waterproof Chelsea Boots
  • Caribou
  • Black/Sea Salt

SOREL Women's Hi-Line Heel Waterproof Chelsea Boots

$189.99

(25)

Comfortable and they look great ... Comfort- so good! ... We are going to New York in December and I wanted a warm waterproofed and stylish boot that is

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5 DTMN
True to size. Love the heel and color. We are going to New York in December and I wanted a warm waterproofed and stylish boot that is comfortable.

5 MT Shortie
I ’ m in love. As a shortie I always want height but am unwilling to sacrifice comfort. These check all the boxes and are so stylish I want to wear them everyday( and I have ~10 pair of other Sorel booties). Just ordered the lace up version. I ’ m always a 9 1/2 in Sorel and these track.

5 Nicole j
These are my absolute new favorite pair of shoes. They give you height and the illusion of heels without the pain of actual heels. I could n't be happier!!

5 LB
Very happy! For some reason, I have to size up a 1/2 size in Sorel. No biggie. I love the color and versatility of this bootie. Easy to get on/off with the elastic and pull tab. Once on, the elastic is not too tight. I wore them for an entire day before I wrote the review to make sure they meet the mark. The back heel almost makes you feel as though you are slightly forward( hard to describe), but not uncomfortable. I wish the bottom of the sole was a little more lug, or aggressive because I am in snow and ice. Did I mention they are waterproof!!!!

5 Julie
These are the cutest boots! Super comfortable, and very stylish for being a winter boot!

New
Dr. Martens Women's 1460 Ghille  Boots
  • Tan
  • Black

Dr. Martens Women's 1460 Ghille Boots

$180.00

Quick Facts

the 2976 boot is our rugged take on the classic chelsea boot. ... built from buttersoft leather in a tonal palette, this 2976 chelsea boot is fitted with antique gold trims to round off the hiker

Chaco Women's Paonia Chelsea Fluff Waterproof Boots
  • Tan

Chaco Women's Paonia Chelsea Fluff Waterproof Boots

$139.99

(14)

grip& trade rubber compound outsole is optimized for wet traction 2. 5 mm lug depth ... non- marking chaco ... soft sherpa- like textile lining women's specific, podiatrist- certified luvseat™ pu midsole adds cushioning and

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5 Lucy
I ca n't wear anything but Chacos. They have a great arch support and are the only shoes that do n't cause me to have ankle pain. These boots were great for winter! Trendy, comfortable and warm.

5 Carol Caye Olds
I love these boots! Great fit, style and above all the fit and comfort are top notch.

5 Dog Walker 405
Warm and comfy I can walk miles in these shoes and my feet stay warm and dry.

5 Amy
Very comfortable and warm. Love the high arch foot bed. I do n't have to wear insoles with these.

5 Meg
Comfortable, and the sole fits like the sandals, which seem to be the only thing that keeps my feet/knees/ankles etc. from hurting. Thanks!

Georgia Boot Men's Eagle One Soft Toe Waterproof Chelsea Work Boot
  • Brown

Georgia Boot Men's Eagle One Soft Toe Waterproof Chelsea Work Boot

$159.99

(36)

I wear them 10 hours a day in the plant and the comfort is excellent. ... Love the all day comfort at work and the easy slip on and off design! ... One, on and off super

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5 ChrisK
This is my second pair, as I have finally worn out my first pair. But it took a really long time, and I have worn them daily for years. The slip on design is convenient, and the comfort is fantastic. These factors, when combined with the protection they provide, make them a truly ideal work boot

5 Mike24
Super comfortable! Perfect Fit! The insoles wear out pretty quick but are still very comfortable. Wish I could find replacement insoles for them that are the same.

5 Adam J
Work and home life do a number on boots. Hold up pretty well as long as my dog does n't get a hold of them. Stiff at first but once they break in, they 're super comfortable. Used to buy the romeos but theres are worth the extra money.

5 GENEG
HAD THIS PAIR FOR 2 YEARS AND WEAR NEALY EVERYDAY.

5 scott72
Been about 4 months now and holding up great so far. Its hard to find a 13 wide that actually is wide enough for my liking and this boot is.

Georgia Boot Men's Athens Chelsea Waterproof Work Boot
  • Dark Brown

Georgia Boot Men's Athens Chelsea Waterproof Work Boot

$159.99

(34)

They are not quite waterproof anymore but they are still very wearable and still look great. ... These boots are awesome, very comfortable all day

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5 ATH
Really love this boot. It is light weight and very comfortable

5 Joe85
The best slip- on boots I 've ever owned. I 've worn this one pair, probably 300 of 365 days a year for the last 5 years. I replaced the insoles at year 3 but thats it. Amazing.

5 ecpirate328
This is the best lasting boot I 've ever had. Most of the time I have to buy new ones after 6 mos due to the soles wearing out. Over a year later, these are still great. Waterproof is great.

5 Libbi P
I ’ ve bought these boots for the second time for my son. He absolutely loves them

5 Matteo
Great boots, comfortable, waterproof good for summer. A little chilli in the winter but a good warm pair of socks helps that.

TOMS Youth Bennett Boots
  • Black

TOMS Youth Bennett Boots

$69.99

Quick Facts

the bennet is the perfect chelsea ankle boot for little ones, crafted from sturdy black nubuck leather with cushy insoles for all- day comfort. ... featuring elastic gore and a handy heel tab for easy on- and- off, this stylish boot is also available in adult sizes so mom or dad...

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