Best Waterproof Chelsea Boots of 2023 – Reviews

I can’t imagine a more durable and versatile bootie for traveling other than the Chelsea brand. These booties were made during Victoria Era in the United Kingdom, as potentially made by Queen Victoria’s very personal shoemaker.

Chelsea boots are the best option for walking and riding before the latest context of cool kids stomp around London’s Chelsea neighborhood to wear them on your feet. So the best waterproof Chelsea boots can take you seamlessly from casual days out to more dressed-up and evening plans.

Due to this, I often wear these booties during my travel between the medieval old town of Edinburgh and the terrains of the Atacama Desert. Therefore, with their iconic silhouette, the chukka and Chelsea is one of the top-rated and best shoes you can wear in the fall, winter, and snowy seasons.

So let’s dive into the detail of all with their pros, cons, and buying guide.

What is Chelsea Boots?

A laceless ankle boot with elastic panels on its side is known as a Chelsea boot. Its clean and streamlined shape is a hallmark of its traditional shape and style. After a few years, there have been many modifications and variations of Chelsea boots, including black and pointed toes.  

What Are the Best Waterproof Chelsea Boots?

Here is the list of waterproof Chelsea boots:

  • 1. Sorel Women Brex Chelsea Waterproof Boots
  • 2. UGG Men’s Chelsea Boot
  • 3. Timberland Women’s Courmayeur Valley Chelsea Boots
  • 4. Sorel Women’s Harlow Chelsea Rain Boot 
  • 5. Ariat Groundbreaker Chelsea Waterproof Boots
  • 6. Georgia Boot Wedge Waterproof Chelsea Workboot
  • 7. Cole Haan Men’s Zerogrand Chelsea Waterproof Boot
  • 8. Sorel Women’s Emilie II Chelsea Boot
  • 9. Chaco Women’s Field Chelsea Waterproof Boots
  • 10. Hunter Boots Women’s Original Chelsea Boot

Best Waterproof Chelsea Boots

1. Sorel Women Brex Chelsea Boots

Sorel Women Brex Chelsea Boots

Sorel Women Brex Chelsea waterproof booties are the best and top-rated boots to wear in the winter season, as these boots come with a modern design and chic style that best complements your wardrobe. Waterproof boots for women are a go silhouette for those busy days in snowy weather. They are made with waterproof full-grain leather and stretch gore panels that offer an incredible slip-on function on outdoor surfaces. 

Moreover, these boots feature seam-sealed waterproof properties and come with a cozy removable molded PU-like EVA footbed to offer more comfort. In addition, the synthetic top cover on top will keep you comfortable and standing in high heels. 

Therefore, you can walk confidently by wearing these boots because they feature a molded rubber sole that gives you texture and better grip and provides traction while moving on various hard surfaces. 


  • Ergonomic design
  • Waterproof
  • Durable
  • Comfortable
  • EVA footbed


  • Stitching broken 

2. UGG Men’s Chelsea Boot

UGG Men's Chelsea Boot

UGG Men’s Chelsea boot is a utility meets fashion boot that meets all weather innovations like a temperature regulating material, state-of-the-art waterproof construction, dynamic support, and a high level of construction. The boots are made with full-grain leather that looks great with vintage denim and a polo collar shirt for most events and situations. Moreover, this footwear is made with pure 100% leather and angry comfort system insoles to offer you comfort.

Furthermore, its outsole features white spider rubber for added traction. It comes with seam-sealed waterproof construction with textile lining to offer warmth to your feet. Also, the brand was founded in 1978 on the coast of California to offer protection, warmth, durability, and a classic lifestyle. 

Despite this, their products have excellent performance in all its products, including Chelsea boots. All designs introduced by this brand are iconic, have an attitude toward creativity, and are a rare example of good art, craftsmanship, and quality.


  • Comfortable
  • Durable
  • Inner soft lining
  • Warmth
  • Long-wearing boots


  • Expensive

3. Timberland Women’s Courmayeur Valley Chelsea Boots

Timberland Women's Courmayeur Valley Chelsea Boots

Timberland Women’s Courmayeur valley boots are made with 100% pure leather that is better than tannery-rated silver for its energy, water, and waste management practices. It also comes with a dual stretch core and a pull-on style. 

The boot’s inner is featured with Rebotl textile lining containing at least 50% recycled plastic. The shoe’s sole has two parts for more flexibility, and an ortholite polythene footbed is best to offer all-day support and cushioning. 

Moreover, the company intends to offer more comfort and durability because they are earth keepers constantly striving to make better footwear products for their clients. 


  • Toe box
  • Comfortable
  • Inner lining
  • Arch support


  • Too small

4. Sorel Women’s Harlow Chelsea Rain Boot 

Sorel Women's Harlow Chelsea Rain Boot

Sorel Women Chelsea rain boot has innovative features like sleek and functional, high-quality upper, and is best for steady walks. It is so functional that you can easily make a statement when you walk on city streets and rough terrains. However, the upper the layer comes with high-grade full-grain leather and gore-tex detailing with canvas and synthetic linings. 

The bootie has a molded rubber outsole to ensure steady walks on slippery surfaces and streets. Moreover, the boot’s insole is very elegantly designed, with a memory EVA footbed and removable die-cut paired with a synthetic top cover for cozy and warm feet. 

To offer you all-day comfort and coziness, the boot has a heel height of up to 1 inch and a platform height of 1 ½ inches for all outdoor activities. The closure type of the boots is slip-on and has a high water resistance level. So, it will be comfortable for your feet.


  • Durable
  • Comfortable
  • Waterproof 
  • Water-resistant
  • Comfortable heel height


  • Narrow from the toe box

5. Ariat Groundbreaker Chelsea Steel Toe Work Boot 

Ariat Groundbreaker Chelsea Steel Toe Work Boot

Ariane Groundbreaker is a boot known for durability and high level of comfort. Groundbreakers by Ariane are made to offer long haul, sturdiness, and style with western detailing. Also, it has extra metatarsal protection, supportive cushioning, stability, and advanced technology to make it ideal for farm work, factory sites, construction sites, and warehouses. 

Besides, it features waterproof material, and it is ideal for those workers who work on construction sites, as it is made with waterproof pro construction. It means that the boot’s upper is fully insulted because it comes with full-grained leather to ensure your feet will remain dry, comfortable, and cozy in hard weather. 

Furthermore, boots are characterized by reinforced steel toes rated with ASTM  and are ideal for hard-working men because they can hold weather elements.


  • Lightweight
  • Comfortable
  • Warmth
  • Steel toe rated


  • No composite toe option

6. Georgia Boot Wedge Waterproof Chelsea Workboot

Georgia Boot Wedge Waterproof Chelsea Workboot

If you want a classic wedge silhouette with upgraded performance and comfort, the Georgia Boot wedge work boot is the right option. The company is still making wedges with true and tried full-grained leather, which is three times stronger and abrasion resistant than traditional leather. With twin gore tex panels and nylon pull-on tabs, you can easily slip on them to ensure a great fit.

Also, it features padded counter pockets to offer additional support in the heel area. Additionally, the insole of the boot is made with AMP memory foam to wrap your feet to keep them warm in all-day outdoor activities. 

Furthermore, the midsole of the work boot has cushioned EVA material and a fiberglass shank for extra stability and support. Carbo tech rubber is essential to the outsole to make the boot more long-lasting and durable.


  • Durability
  • Comfort
  • Waterproof material
  • Padded counter pockets


  • The width is not so good

7. Cole Haan Men’s Zerogrand Chelsea Boot

Cole Haan Men's Zerogrand Chelsea Boot

Cole Haan Men’s Zero grade is a product of the Chelsea brand and was introduced in the USA. The outer of the work boot is made with pure leather to offer more traction and water-resistant qualities. It has premium waterproof leather and a side core to ease entry. 

All the construction in the boot is made with waterproof fabric to keep your feet dry and comfortable in most wet conditions. Besides, the heel rubber pods and the footbed provide added durability and traction on hard surface areas. 

In addition, the boot is featured with molded sock liner to give the workers a high level of cushioning and comfort on hard sites like construction, camping, and hiking. Therefore, it makes your feet more comfortable in any work you do because it comes in true size with lightweight, versatile, and comfortable materials.


  • Highly comfortable
  • Long-lasting
  • True size
  • Great boots with five stars


  • Bigger size than expected

8. Sorel Women’s Emilie II Chelsea Boot

Sorel Women's Emilie II Chelsea Boot

If you want simple and modern ankle boots, Sorel women’s Emilie II work boot is the best option. It has an iconic cate block heel to offer signature style and protection in all-day outdoor activities to a greater extent. 

These are waterproof rain boots for women with full leather upper with sleek and versatile design with included stretch panels to put on and off with ease and comfort.

With suede and leather upper with cozy die-cut memory EVA footbed, it offers comfort and cushioning for all-day-long exertions and activities. You can walk securely with these boots due to molded rubber soles with high traction to protect your feet during long walks and keep you standing tall in all outdoor activities. 


  • Comfortable
  • Leather and suede material
  • Waterproof
  • Secure fit


  • Tight from toe

9. Chaco Women’s Field Chelsea

Chaco Women's Field Chelsea

From urban landscapes and mountain towns, the Chaco field boot is built to offer more comfort and durability to all those women who work in the fields. It also comes with a great heritage style, Gold rated leather and canvas lining on the inner side of the boot for comfort that never goes old and outdated. 

So, full grain and pure leather with waterproof material make this boot different from other footwear. That’s why it is best to do this in a competitive market. 

Sem-sealed construction paired with pigskin leather and canvas lining makes outdoor activities more comfortable and warm, especially in winter and the snowy season. It has a skid-resistant tread design, Chaco rubber compound, PU footbed instant, and comfort EVA midsole to enhance its look. 


  • Skid-resistant tread design
  • Perfect fit
  • Nonmarking grip
  • Instant footbed


  • Slightly expensive

10. Hunter Boots Women’s Original Chelsea Boot

Hunter Boots Women's Original Chelsea Boot

As the name indicates, the original Chelsea boot is ideal for hunters. And it comes with more functions and designs. You can easily exercise confidence when you want to embrace elements in style with these work boots. It features an eye-catching monotone design that is a great addition to pop its look. 

Therefore, the waterproof natural rubber construction lets you keep your feet dry in most wet conditions. It is very easy to wear because of the easy pull-on design, with the pull tab on the rare side. 

In addition, it is an excellent example of a classy look, with a round toe and seamless construction in its upper and sole. It fits any size of feet perfectly because it is made with dual goring panels to offer easy wear. 


  • Perfect fit
  • Classy look
  • Easy to wear
  • Pull-on design


  • The size is very small

Buying Guide for Best Waterproof Chelsea Boots

Same as your shaking hand, the first thing that people notice is the footwear you are using. So to help you buy the best Chelsea boots, whether to opt for leather suede, I have gathered the essential features to look for in the best affordable Chelsea boots. 

High Quality

Investing in a pair of high-quality Chelsea shoes would be the best option because they will last longer, and you get the most wear out of your purchase. 

So always look for the boot’s quality rather than compromise on a lower price. Every feature should be made with top-rated material from elastic to heels, uppers to soles. 

Moreover, remember that the elastic panels’ quality will determine the boot’s life. If poor elastic is used in its panels, it will loosen with time with stretching after wearing it for years. 

Ankle height

The main purpose of Chelsea boots is to cover your ankle, thus offering you great comfort. It will also add protection for your country wear and makes it a popular option to wear during hiking and horse riding.

Low Heels

These work boots come with low height as they are used for walking normally instead of high carbon heels.

Rounded Plain Toes

Typically they come with round toes and a plain toe having no designs and details on the vamp, thus creating a clean look. However, some options are growing on trend with chisel square toes and brogue patterns. 

Handy Pull Tugs

Slip-on Chelsea boots should have a snug fit. To make it easier on and off, pull tugs on the front and rear of the boot with the combination of static sides to ensure snug and comfortable wear. 

Minimalistic Style

The most popular style in Chelsea boot with clean lines that makes them more enduring. A dark color Chelsea boot with low heels is never outdated and out of fashion. So if you are buying your Chelsea boots for the first first time, you should go for the plane style instead of selecting with patterns and designs. 

So stay clear, chunky tall heels with high shine pure and patent leathers. Moreover, with more design frills and embellishments on the boots, they will go harder in style and fashion. The simplicity they come with makes them more adaptable and wearable. 

Rubber Soles and Leather Soles

A traditional Chelsea boot comes with a leather sole, but the market is full of those options featured with high-quality rubber soles. Rubber soles are harder for casual wear because you use Chelsea boots for regular walks and outdoor activities. 

Moreover, rubber soles offer better grip on hard surfaces, terrain, mud, and rain, while leather boots are ideal for the timeless elegance of real Chelsea and dress boots. 

Therefore, you should look for a decent sole in your Chelsea boot. Whether you buy a boot with a leather or rubber outsole, it should be well-welted and Goodyear welted. So, the sole can be easily repaired over time, offering you a lifetime of wear on most events. 

Tapered or Rounded Toe

A Chelsea boot with a classic look is featured with a rounded toe. But you can look for square tow that fits your taste. However, the more tapered the toe, the dressier your boot will be. 

So it is best to opt for the boot with neither clown shoes bulbous nor severely pointed. 

Quality of Elastic Sides

Also, the most important factor is the elastic quality used in the boots’ panels for their longevity and shape. The elastic function in Chelsea boots is to hold the boot to your ankle when you get the snug feel while wearing them. 

So to get this snug fit, elastic on the sides of the boot should be of good quality. If you feel it is not providing resistance when you put on your boots and elastic stretches too easily, it will not last long in many situations. 

A Brief History of Chelsea Boots

Chelsea boots got their name and originated from the fashionable district of London.

Chelsea was a center of music and fashion designers during the 1960s as they recreated a style of their footwear or ankle boots because Queen Victoria first wore them in the 1840s. A shoemaker named Joseph Spark s Hall made a traditional English riding boot for everyday use worn by her. 

To offer more comfort and durability, he lowered the height of the shaft to the ankle for easy on and off, with the added gussets made of elastic on each side. This style disappeared during WWI and became popular in late 1800. Then it was forgotten for half a century till the fashion look Victorian style took off in London during the 1960s. The Victorian ankle boots come in tren again, along with lace-cuffed shirts and cricket jackets. 

The boots became popular in the areas where most fashionable people of the UK were residing and came out for hangouts. Then during the 2000s, they came into fashion again when Tom Ford and Saint Laurent sold these boots, and this trend reached a crescendo in 2016 when Justin and West lived in Chelsea. 


Should I size up or down Chelsea boots?

Chelsea boots come in true size, so there is no need to have up or down a size. 

Are Chelsea boots in fashion for 2023?

Among the most popular and trending boots of 2023, we cannot ignore Chelsea boots forever. They are not in a proper trend but rather carryover from year to year. 

How do you know if your Chelsea boots are too small?

Your Chelsea boots should be constructed but snugged. Without laces, you should ensure that the boot grips your ankle and heel best. 


By saying that maybe Chelsea boots will fall at this moment, they will peak in popularity for many other reasons. They will be in men’s fashion style for the next half-century. 

Countless designers, fashionable people, and celebrities have used these boots for a long time due to their foundational price that can complement most outfits. 

Soon enough, when the air catches a chill and days grow shorter, everyone will wear Chelsea boots for every event like so many crispy leaves blanket the ground. 

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