Best Chelsea Style Boots Reviewed & Rated
Richard Haberkost 
Team WJR An excellent choice for fall and winter wear, Chelsea boots are a great addition to anyone’s closet, seeing that they can easily be dressed up or down. Appropriate for work<, casual wear, and even with a suit, they come in a wide variety of designs and styles, from simple and elegant, to rugged, even to those with broguing and colorful details, allowing you to show off your personal style. With a huge number of models available on the market, it may be difficult to find the best one for you. That’s why we compiled this list of the ten best Chelsea boots available for purchase, with options for every budget, style and color preference.
This is the best product on our list that is currently in stock:
Genuine Leather Upper
Soft Leather Lining
Natural Cork Footbed
Antimicrobial Insole
Studded Rubber Outsole
Top 10 Comfortable Chelsea Boots
1. Timberland Logan Bay
Leather Upper
Rear Pull Loop
Anti-fatigue removable footbed
Gripstick Rubber
Steel Shank
Runs Wide
Timberland - the name says comfortable, functional footwear and this model lives up to the reputation of their maker. This oiled leather pair looks rugged and solid and ready to hit the road on a Harley. It’s comfortable inside too so don’t let that rugged look fool you into thinking this is a rough pair. It’s a fantastic addition to your wardrobe.
These Timberlands feature an anti-fatigue removable insole for comfort. The side goring is concealed behind strips of oiled leather for a unique look but also for additional protection for your ankles whether you are working hard or playing hard when wearing them.
They are in the mid-range in price for the shoes on this list. For the investment though you are getting Timberland comfort and functionality combined with a rugged, oiled leather look and extra protection for your ankles. Worth the extra money.
2. Frye Grady
Full-grain Leather Upper
Leather Lined
Leather Sole
Goodyear Welt Construction
11-inch Shaft Height
Expensive
No Traction Pattern
If you want a pair of footwear that will make you look and feel like a real cowboy, then the Grady sure is a good choice. Made by Frye, this quality item is sure to last a lifetime, and you can rest assured that it will get better looking and offer a higher level of comfort the more you wear it. It is available in several color options including black and brown which are easy to pair and can be dressed up or down depending on the occasion.
The upper of the Grady is made with full-grain leather which is either brushed or smoothed, depending on the color option you decide to go with. Easy to take care of, this material will provide breathability, all the while allowing you to break your boots in to fit you like a glove. On and off is relatively easy thanks to the elastic finger goring on the sides, while the 11-inch shaft provides a good amount of ankle stability.
Both the lining and the outsole of this model are made with leather, so you can expect a cushioned, soft feeling underfoot. It will require a break-in period, but you’ll find that these boots will become your go-to everyday option. The construction uses a Goodyear welt which means these can be resoled and repaired as needed, but do keep in mind that they won’t be suitable for wear in rain or snow.
The price of this item depends on the color option you decide to go with. You’ll find that most models go for a price that’s considerably higher than average, being one of the most expensive items listed. Nonetheless, if you’re after something that will be more than just an accessory, and that you’ll feel pride in owning and wearing, the Fry Grady is a great investment.
3. Thursday Boot Company Duke
Genuine Leather Upper
Soft Leather Lining
Natural Cork Footbed
Antimicrobial Insole
Studded Rubber Outsole
Lacks Support
Runs Large & Wide
It's hard to go wrong with a product made by the Thursday Boot Company, and the Duke is no different. Made for those who prefer elegant style, high quality materials and some of the best quality control in the industry, it'll definitely be the pair of shoes you reach for every morning when you're headed to work. You can choose between suede or leather for the upper, and get either a black, brown or tan color that'll be easy to match with a variety of outfits from jeans to suits.
The upper of this boot is made either with quality leather or with water-ready suede that will stand up to unexpected showers. However, it's the Goodyear Welt construction that ensures a waterproof and durable pair of footwear. The outsoles are made with studded rubber for a good amount of grip even on wet surfaces, so you can rest assured that this is a great all-round model for all types of weather conditions.
The Duke features a full glove leather interior that'll be soft to the touch while providing a good amount of breathability in case you've worked up a sweat. The footbed is made with natural cork that adapts to your arch, providing you with great arch support, while a Poron insole ensures excellent shock absorption and antimicrobial properties.
4. Red Wing Weekender
Oil-tanned or Roughout Leather
Stutchdown Construction
Cork Midsole
Made in the USA
Repairable and Resolable
Heavier BootExpensive
Tight Around Ankle
This pair of 6-inch boots by Red Wing is the perfect choice for casual, comfort-oriented wear. Part of the brand’s Heritage line, this model uses high-quality materials and is made in the USA for the highest possible level of quality control. It is available in four color options including black, copper, olive and brown, and will look ideal with a pair of jeans.
The upper of the Weekender comes in a couple of leather options, both of which provide different benefits and looks. The oil-tanned leather uses minimal finishing and offers a natural look and feel. Being durable, it also offers the benefit of being water, stain and perspiration resistant. The roughout leather styles, on the other hand, provide a rugged look that is softer and easier to break in. These will, however, need a higher level of protection, seeing that they’re less resistant to moisture.
The construction of the Weekender uses a stitchdown last which offers exceptional flexibility and out of the box comfort. The Hill sole offers a good amount of traction that will last for plenty of time, while the cork midsole and leather insole provide wearers with a great level of support and cushioning.
Like all Red Wing styles, the Weekender is fully repairable and even resolable, which allows you to wear the same pair of boots for years to come. Additionally, you’ll find that these products provide maximum wearability, not only because of how good they feel on your feet, but because of their versatility as well. Do keep in mind that this type of quality comes at a price higher than average.
5. Blundstone Dress
Leather Upper
Rubber Sole
Anatomic Footbed
Stabilizing Shank
PU Midsole
TPU Outsole
Fits Wide
Classic Australian Blunnies. These shoes look great and are appropriate for kicking around or working. They feature a steel shank for stability, extra shock-absorption in the heel and a premium leather upper. The footbed and PU midsole make it very comfortable for long hours on your feet.
The footbed in this model is anatomically shaped and removable. You can wear your own custom insole or orthotic if you wish. The Blunnies Dress features a steel shank in the midsole for stability and Blundstone's Prono XRD shock protection in the heel strike zone for extra shock-absorption, reducing soreness and fatigue in the heel and ankle.
These shoes are very much an investment, but you will be getting one of the most popular models for the money. The reason they are so popular has nothing to do with the name and everything to do with their quality, comfort, and wearability. Work all day in them without aches or pains and still have the energy to walk around doing your errands at night.
6. Joules Wellibob
Rubber Rain Boot
Rounded, Roomy Toe
Abrasion Resistant
Textile Lined
Fixed Insole
A colorful, fun rainboot in the well-known style. These are a cute rainboot for working in the garden or just keeping your feet dry while walking around town. They come in a variety of printed rubber toppers from solid black, to geese to floral designs to allow you to express your individuality and sense of fun in your rainboot. Comfy padded footbed too!
These are a very durable pair with a rubber upper and rubber. Apart from being cute, they are also waterproof and abrasion-resistant, so they will last you a very long time. Who can be dull and grey like rainy, overcast weather when you’re wearing boots with bright floral prints, vivid stripes or airy, flying geese? You can’t is the answer here! They are fun and all expressive sunshine.
These boots are a great value at the low end of the price range. For the cost, you could get the chihuahuas and the floral print to mix up the fun. They are a great rainboot with the wide-mouthed style and comfortable padding too - not just for working in the garden!
7. Dr. Martens Hurston
Semi-aniline Leather Upper
Air-cushioned Sole
1-inch Platform
3.5-inch Heel
Effective Traction Pattern
Limited Color Options
These pull-on heeled boots by Dr. Martens are the ideal choice for anyone looking for a good combination of quality and style. They offer a feminine look with a touch of rebellion, and can be combined with a number of outfit combinations. Not only are they versatile, but they’ll also offer a good amount of protection from the pain associated with walking, can be worn in wet weather conditions, and are relatively simple to maintain.
The upper of the Hurston is made with genuine leather treated with Analine to achieve a natural look and high durability. It is moisture-resistant, making these heels perfect for fall, and the fit is made better through the addition of elastic panels, as well as a Doc Marten heel pull tab.
The outsole of this model is built on the same principle that’s used in making traditional Dr. Martens boots. It utilizes an air-cushioned AirWair sole that does a great job at absorbing shock and providing a comfortable surface to walk on. The 1-inch platform and 3.5-inch heel aren’t too tall for everyday wear, while the pattern on the bottom of the boots offers a good amount of traction that’ll work on varied indoor and outdoor surfaces.
As for cost association, the Dr. Martens Hurston ranks around average compared to the other models listed and is an excellent choice for those who want a good balance between price and quality.
8. Ariat Spot Hog
Genuine Leather Upper
Round Toe
Everlon Technology
EVA Foam Midsole
Front and Back Pull Tabs
Traction
Sole Durability
These casual pull-on boots by Ariat are an excellent choice for those who lead an active lifestyle, but still, wish to invest in footwear that will look sleek when paired with jeans or trousers. The Spot Hog features a 5-inch shaft, comes in three color options and two choices of material. Our favorite has to be the peanut colored smooth leather upper, but the lighter and darker versions can be just as versatile and stylish.
The most important feature of the Ariat Spot Hog has to be the EVA foam midsole which is a type of shock-absorbing material often used in running sneakers and athletic footwear. EVA is very lightweight and is a cushioning compound that adjusts to the foot and can help ease joint and muscle pain associated with long hours of standing and walking.
The entire sole unit uses Everlon technology to increase durability, giving both the midsole and outsole the properties of blown rubber. While this ensures a lower degree of flattening and wear, it also provides a higher level of energy return which is important for those walking long distances. The bottom of this boot features a chunky traction pattern that is adequate for most weather conditions, however, keep in mind that it won’t perform too well on ide or surfaces where it can become clogged.
The cost association of the Ariat Spot Hog is average, allowing users on a budget to still receive a high-quality product made with real leather and some great comfort technology.
9. Blundstone Original
TPU Outsole
Toe Spring
Premium Thick Leather
Protective Leather Upper
Shock-Absorbing System
Finish Appears Dull
The Original Blundstone that started it all, this is one tough, comfortable boot. You can take it anywhere and work all day in comfort. It’s made of a premium, thick leather for protection and durability. They also feature a toe spring, reinforced stitching and a soft leather and textile lining. They are rugged and will take you anywhere you want to go.
The outsole on these Blundstones is made from thermoplastic polyurethane which provides good traction and much longer wear than other outsoles. It is also oil, acid and fat resistant, making them great in a kitchen. They should last you years.
The leather upper is thick, protective and medium-quality. It is weather-resistant and rugged, ready to take on almost anything. Blundstones are an investment, at the higher end of the price range for shoes on our list. However, like the Dress Blunnie, these are worth every penny for the quality, comfort, and durability you are getting. These are a little tougher than the Dress and should last longer before having to be replaced.
10. Skechers Blaine Orsen
Leather
Rubber Sole
Ankle Length
Deep Traction Lugs
Sizing Varies
Durability
The Skechers Blaine Orsen is a sturdy pair with a bit more rugged styling. Quality leather creates the uppers with decorative stitching that’s also functional to hold the panels together. Rounded toe gives ample room for comfort, and a pattern lug sole provides traction on all sorts of surfaces. Suitable for work or play, it’s a great all-around look that can complement most any ensemble you pull together.
Uppers of the Blaine Orsen have been constructed form quality leather, durable yet pleasing to the touch, and ready for whatever wear and tear you throw at them. Panels are carefully stitched together, and elastic side gores are hidden from view by a panel of stitched leather. Heel and tongue pull tabs make it easy access to pull onto the foot.
Slightly more rugged in its appeal, the Blaine Orsen can be worn for both casual settings, business attire, or when paired correctly, for some formal events. Its rich oiled leather gives it a smooth finished look, while rugged sole allows for traction in any kind of weather or on uneven surfaces. Rounded toe gives room for walking over long periods of time, without getting sore feet.
Criteria Used for Evaluation
Features
To make our list, the footwear we looked at had to have the traditional characteristics of this style. Here are things to look for when shopping for men's and women's ankle boots:
Durability
These shoes are meant to be durable top and bottom. In most cases, not all, you are investing quite a bit of your hard-earned money into the pair you have chosen and you deserve to have it last. What makes it durable?
Comfort
If you’ve read a number of our criteria sections, you will have seen that we talk about comfort quite a lot. There are a few reasons for this:
When you purchase a shoe online, you do not want to be surprised to discover that you’ve purchased a shoe so uncomfortable you will never wear it again.
Here are some brief tips about the comfort of a good pair:
Color
Color is what holds your entire outfit together and unifies the whole look. On top of that, you give off a different impression on others based on the tones you wear. It’s been proven color is a powerful tool for communication that can influence mood and actions? Did you know, for example, that red provokes warmth and even hostility while blue induces a feeling of calmness and sadness?
Scroll through our list and you’ll find that the majority of their footwear and clothing are neutral-colored. It is, after all, a store for men, who often dress more subtly than women. Plus, there are numerous benefits to neutral-colored shoes, including their versatility and formal look.
When picking out a pair, there are some things to consider. It is advised for men to match the color to that of their socks and belt. This helps to unify your overall appearance. In addition, wear shoes darker than the pants in semi-formal or formal occasions - note that the recent white sneaker trend has turned the tables when it comes to casual streetwear. If you’re opting for a pair that’s not white, grey, or black, make sure the color matches or compliments the rest of your attire to avoid clashing.
Value
When deciphering what makes a brand valuable it’s so much more than something as minor as good marketing. The culture and history of a company have a trickle-down effect. The best brands add value not only by choosing quality materials but by creating a culture of excellence. Employees are the meat and potatoes of any company and when they are at their best products will be innovative and stylish. The construction of an item, like; hand-stitching, genuine leather, wool interior, and other quality materials will in-part determine what really constitutes an item that is considered valuable. Classic designs that any brand is known for has stood the test of time. Signature designs can be counted on for quality and consistency. Companies that boast a classic line that maintains its quality over time and is actively creating innovative outerwear is constantly growing for a reason. It’s not always easy to find a line that gifts provocative cutting-edge styles while maintaining the quality of pioneer designs. Correct pricing is important a name doesn’t always mean a superior item. Things like a balanced stride, slip-resistance, comfort cushioning and an interior that warms or wicks depending on its purpose, are all apart of thoughtful appropriate design and add value.
Expert Interviews & Opinions
Features Durability Comfort Color Value
There are so many versatile options you have when pairing chelsea boots! For business attire, pair a classic black pair with a nice suit, or slacks and button down. You can do a little bit of a rocker fashion when paired with skinny jeans and leather jackets, or everyday casual with regular jeans and your favorite top.
The name of the fashionable chelsea boot became popular from the 1950s and 60s, where pop culture combined with Kings Road in Chelsea put them on the map.
Other Factors to Consider
Bottom Line
We spent many hours looking for the best pairs of Chelsea boots available on the market, to suit a variety of needs and tastes. We’ve come up with a list of 10 of the very best ones. There is something on our list to satisfy everyone and one for every member of the family. Depending on your needs, there is a shoe on this list that will suit you. Whether you're looking for an inexpensive style, a pair that lasts forever, a rainboot, a snowboot, or one that is great for work but also works for play, you will find it here - our list really does contain something for everyone.
Frequently Asked Questions
q: Are these a new style? I’ve only really seen them in the last few years.
Ah, fashion. Everything old is new again. They date all the way back to the Victorian era, when the streets weren’t so very clean and good footwear was a necessity. They were worn by both men and women. They also saw a surge of popularity again in the 1960’s among the mod crowd. They are now seeing another surge of popularity for their stylish look, durability, and ease of use. The name became attached to the boot in the 1960s, named after a street in London, England.
q: Are there variations of them? I’ve seen styles with pointed toes.
Yes, there are several variations. One is a pointed toe variation that was created for the Beatles and are often called “Beatle boots” and another is the jodhpur model, a specifically designed one for horseback riding.
q: What is goring?
Goring is elasticized paneling that is added to shoes to help in getting them on. It is also used in jodhpurs and a lot of slip-on styles like loafers.
q: The synthetic leather on my boot is peeling away. Is there anything I can do about that?
There are repair kits that you can purchase for synthetic leather peeling. However, these kits are not cheap and it takes quite a bit of time and talent to use them in a way that isn’t readily obvious. It’s often not worth the money and time to replace a synthetic upper. Read reviews to avoid this problem and know that inexpensive synthetic leather shoes are not going to hold up as well as genuine leather and higher quality synthetics.
q: Size guides are so confusing, why should I waste my time figuring them out?
Like anything else, they do become easier to read the more of them you are exposed to. They are worth reading because no two manufacturers will make shoes in exactly the same size or the same way. And no manufacturer can even be said to create two different shoe models in exactly the same size or way. Reading the size charts and guides is a good way to ensure your purchase will fit your foot. Also reading reviews will tell you if the size chart is accurate. Most are but not all.
q: When a shoe is described as a fashion shoe, what does that mean?
It usually means that the shoe was built with its appearance as the primary design aspect and less focus may have been put on the other aspects of the shoe. For example, functionality, comfort, and durability may be sacrificed for the look of the shoe.
q: I’m a vegan for ethical reasons but I really love this look. Are there options for me?
Several of the models on our list are made of synthetic leather and one entirely of rubber. One is even specifically made of vegan leather. When looking for vegan-friendly shoes it is important for you to carefully read the specifications. You can also post questions on many online buying sites. The manufacturer or experienced consumers may tell you whether the synthetic material is vegan-friendly.
q: Leather or suede? I can’t pick!
Sorry, can’t help you there. Leather and suede are both great and the choice will be a personal one to you. Think about where you want to wear them, how they might scuff, what outfits they will match and you’ll soon have your answer. Either way though, if you purchase quality, you won’t go wrong and you’ll rock the look.
q: So excited that I received a great pair for my birthday. But what do I wear with them?
They are designed to be a little slim so skinny jeans look great with them but so do straight cut jeans and pants, skirts, dresses, and capris. You can pair them with whatever makes you look good and feel good. These are a very versatile style. Younger folks are creating their own styles and don’t get bogged down by stiff fashion rules anymore, so go with what makes you happy.
q: Oh man, the leather is cracking on my pair. I’ve had them for years and I don’t want to give them up. Help!
Cracking leather can be caused by a number of factors - UV radiation exposure (i.e. too much sun), excessive aridity (desert-like dryness), heat, and chemical exposure. First, clean it carefully with a dry cloth. Using a damp cloth with a leather cleaner, gently clean the leather being sure to wipe away any residue with a clean damp cloth. Apply a good quality leather conditioner and work it in according to the manufacturer’s directions. Allow them to dry and then treat them with a waterproofing sealant to restore their water-resistance. Be prepared to treat them with the conditioner again in a week or two to help further restore the leather. If the cracking is very deep or has created a hole, you may have to just give up and replace your pair, or take it to a cobbler to see if they can do more for you.
