Best Fall Boots Reviewed & Rated

As the air turns from humid to crisp, and the leaves begin their kaleidoscopic change, you find yourself putting away your summer clothes and tugging out your warmest flannels, snuggest sweaters, and knit caps. The centerpiece to any autumn ensemble cannot be neglected, however, and manifests in that singular item that conveys both function and fashion; fall boots.

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By Nina:

We've added some stylish options for slouchy and tall ones, classy work and chukka styles, and some new brands to vary selection. All trendy for 2018, and all sure to keep you warm when cooler weather hits!

Whether you live in a place where autumn means plenty of precipitation, or where the sun is always shining, the right choice of footwear will mean the difference between having a fun autumn season or suffering through that transitional period that is neither here nor there, wearing footwear that is inadequate and leaves you frustrated at the end of the day. There are lots of features to consider before making a purchase, as different climates will require different types of shoes. You may want to get some with thick soles for good traction, or you might be considering whether lace-up tall ones for the outdoors will fit your needs better than an efficient slip-on ankle ones for work.

Featured Recommendations

Dr. Martens 1460
  • Dr. Martens 1460
  • 5 out of 5
    Our rating
  • Hard Synthetic Sole
  • Durable upper
  • Price: See Here
  • BEARPAW Emma
  • 5 out of 5
    Our rating
  • Fur Lined
  • Insulated
  • Price: See Here
  • 5 out of 5
    Our rating
  • Knee-High
  • Adjustable Tie
  • Price: See Here

Whatever route you go with your footwear, make sure it speaks to your personality, has the key features you want most, and has a price tag that is reasonable and reflects the quality and durability you are looking for. To help you prepare for the season, we’ve compiled a list of the top ten options to make your decision easier.


10 Best Fall Boots


1. Dr. Martens 1460

No other model pairs with a bold and bright outfit quite like a pair of 8 Eye Patent Leather Dr. Martens. They are durable enough to be worn both at work and during your off hours, but provide you with a look that is the perfect combination of polished a rugged, making these a fashion statement that has a punk edge. The Dr. Marten’s brand is synonymous with individuals that make their own mark on the world, so wear these and march to the beat of your own drum (coming from a Nirvana compilation).
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The 1460 came out in 1960, and has never been out of production. It has an 8 eyelet upper that comes in numerous colors, and is made out of the classic Doc smooth leather. They are tough, and you can rest assured they won’t scuff easy, with an air-cushioned sole that makes them surprisingly comfortable. The leather ensures that over time and with proper care, they’ll begin to mold to your foot. They’re resistant to oil and fat, as well as being slip and abrasion resistant. Made with Goodyear welt, the upper and sole are heat sealed and sewn together, which means they won’t come apart as easily as other footwear.

Dr. Martens are incredibly versatile, despite being popularized mostly by the punk elite in the United Kingdom in the late 1970’s. They have the commanding presence of a boot that can be used to make a feminine outfit more masculine or, because of their polished exterior, give an edge to a finely tailored suit. Have them stand out by cuffing your stovepipe jeans like 60’s British dock workers, or have their round shiny toes peek out from under a long flowing skirt. Because they come in a variety of colors as well as prints, the sky is really the limit with this incredibly versatile and popular model.

Cost and Value
Dr. Marten’s aren’t cheap by any means, but then again, they had been assembled in the same factory on Cobb Lane in Nottinghamshire up until very recently. The quality of the brand is well known and can be seen in its great styling, its thick lug sole, and eye-catching yellow stitching. After you find the perfect pair for your personality, you’ll get years of wear out of your Docs. Just remember, the break-in time takes some time but after a while, they’ll fit you like a second skin.
  • Quality materials
  • Thick lug sole
  • Polished full grain leather
  • Comes in a variety of colors/prints
  • Air cushion outsole
  • Take a while to break in
  • Quite heavy


This model by BEARPAW is perfect for women looking for a comfortable and casual style that will look good with jeans or even a casual skirt or dress. Available on Amazon in 14 colors, you are sure to find a pair that you will want to own. What makes them great is the soft upper that will keep you comfortable even with all-day wear, while still providing you with the warmth that you might need during the colder months.
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Cow Suede Upper
The upper of the BEARPAW Emma is made out of cow suede which is soft to the touch, yet durable and breathable. They are lined with a sheepskin and wool blend lining, making them warm, without the use of synthetic materials. This means that you can rest assured that odors are less likely to develop, while moisture generated while walking will evaporate more easily.

Flexible Outsole
Their outsole is made out of TPR rubber, and is a low profile outsole that can easily be worn outside and inside. An additional feature is that the outsole is non-marking, making these shoes the perfect choice if you need to keep the surfaces you walk on daily nice and clean looking. Even more, the TPR rubber provides the wearer with plenty of flexibility, making them suitable even for use around the home.

Cost and Value
Depending on size and color, you could get the BEARPAW Emma for a relatively cheap price. Nonetheless, they are made of real leather, and some styles might cost you more than the average item on this list. They could be perfect for you if you are looking for a style that is comfortable and warm, but which you don’t plan on wearing in rain or snow, seeing as they are not water resistant.
  • Cow suede upper
  • Wool lining
  • Flexible rubber outsole
  • Variety of colors
  • Available at low prices
  • Not water or snow resistant
  • Soles might get slippery on some surfaces

3. Clarks Desert Chukka

One of the classic boot styles, the chukka, is an ankle length bootie with simple lace vamp and more formal design. These can be paired with slacks for work or more formal occasions, but also go great with a pair of jeans, cuffed or straight, when out with friends. The Clarks Desert Chukka also keeps you stepping in comfort, with footbed design and cushioning for those who are on the go.
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The Clarks Desert Chukka has simple suede leather uppers with a clean look, and is available in several colors and designs. A crepe sole keeps your steps light, and maintains traction when you need it with its sticky base. A low stacked heel gives some your swagger some confidence, and the simple lace vamp allows for some adjustable fit, and gives a flair of sophistication in styling.

Clarks knows comfort, and keeps the Desert Chukka functional for the entrepreneur on the go. A suede lined heel counter helps to stabilize and support your steps, and minimizes any heel slippage that can occur when walking. Rounded toe allows for a roomier fit in the toe box, and allows for better comfort when walking to your next appointment or outing.

Cost and Value
Averagely priced for those on our top ten list, the Clarks Desert Chukka is really quite a steal for a staple pair to add to your collection of footwear. Its more formal design gives it the versatility to go from the office to happy hour, while brand name secures that you’ll be comfortable all day when wearing. A solid purchase for those looking for a go-to pair this autumn.

Crepe Sole


Rounded Toe




Not Waterproof

Require Break In

4. Thorogood American Heritage

4. Thorogood American Heritage
Thorogood's footwear is made by workers in the United States with the use of high quality materials and with technologies that ensure excellent comfort, practicality and a long lasting wear. Available both in a non-safety toe and a steel toe version, this pair could either serve as your next pair of work footwear or something you wear when the weather gets colder. With their Goodyear storm welt construction, you can rest assured that they will serve you well in all conditions, while still giving you an attractive, versatile style.
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Genuine Leather Upper
Their upper is made out of oil-tanned leather, and is available in four different colors. Their 6' height will cover your ankles, giving you both support and stability, while also ensuring some additional warmth when the weather starts turning chilly. You will definitely appreciate the cotton drill vamp lining which is there to give you a softer feel around your ankles.

Durable, Ready for Work Outsole
The outsole is a Single Density Polyurethane MAXwear Wedge Outsole with a composite shank for added stability. It is slip resistant, s well as abrasion, oil heat and chip resistant. The midsole is made out of rubber for good shock absorption which will protect your joints, while the insole is a Poron comfort cushion insole with a removable shock absorbing footbed.

Cost and Value
Considering the fact that they have been made in the USA using genuine leather and plenty of safety features, these shoes come with a very reasonable price tag. If you decide that the Thorogood American Heritage is the right shoe for you, you are bound to get a pair that you will want to wear all year round, and that is sure to serve you well for a long time.
  • Goodyear storm welt construction
  • Removable cushioned insole
  • Leather upper
  • Excellent grip on all surfaces
  • Shock absorbing midsole
  • Not waterproof, but can be treated with water repelling products
  • May require breaking in

5. Red Wing Iron Ranger

5. Red Wing Iron Ranger
This model by Red Wing, a company that has been around for over 100 years, has become iconic through its high quality of make, durability and classic, timeless style. Originally made for miners from Minnesota, these shoes feature a double-layered toe cap, oiled leather and a nitrile cork outsole that is oil resistant and provides excellent comfort that only gets better with wear. One of the great things about Red Wing is that they have their own repair facilities so that you can rest assured that whatever happens to them, you will have the option of repairing them with free shipping on services above $50.
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Oil-Tanned Leather
They are made from oil-tanned leather from the S.B. Foot Tanning Co., and are water, stain and perspiration resistant. This type of leather uses less additional materials in the production process, allowing for a more natural look that is still very practical. When they are still new, they will feel comfortably tight on your feet, molding to your foot shape through wear and time.

Nitrile Cork Outsole
The outsole of these shoes is made out of nitrile cork which is oil and water resistant, and provides better traction than leather, and more durability than rubber. Thanks to the cork components, it also provides you with better padding and shock absorption, and it will mold to the shape of your foot over time. The insole of the Red Wing Iron Ranger is made out of leather, for durable, all-day comfort. Red Wings are constructed using a Goodyear welt which ensures that you have a durable pair of shoes that won’t come apart at the seams.

Cost and Value
While they aren't the most expensive on this list, they will require an investment. Red Wing footwear is made to last and to get better with time, and with the proper care, you could be looking at a lifetime spent wearing it. You will love wearing them in spring and autumn, however, the outsoles won’t provide you with good enough traction in icy conditions, so you may not get much use out of them during winter.
  • Oil-tanned leather
  • Water, oil and perspiration resistant
  • Good traction on most surfaces
  • Double layered raised toe cap
  • Leather lining
  • Require a break in period
  • Run about ½ size large

6. Dream Pairs OTK Slouchy

6. Dream Pairs OTK Slouchy
If you’ve not tried over the knee (OTK) ones yet, this is your chance! As one of the trendier styles for autumn 2018, a good pair can really add a bohemian style to your wardrobe, or just keep your casual look amped up a bit. Dream Pairs OTK Slouchy is a soft and cozy pair that you can let slouch as low as you like, or tie up and secure with the boot opening tie to keep them high over the knees. A great option for cooler weather!
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Slouchy Style
This model that has a slouchy style to it gives it a casual kind of appeal, but when designed properly, it can add a luxe element to your attire. The OTK Slouchy is constructed with synthetic uppers which are soft to the touch, an inner zip, and back lace closure. Soft faux fur lines the top of the boot, helping to keep you warmer in cooler weather. Slouch the boot down and pair with thick knee-high socks, or tie up over the knees to pair with shorter dresses and skirts.

The OTK Slouchy is a low heel boot with rounded toe, so you’ll be able to walk easily and comfortably in these for the day. A cushioned insole and soft lining help add some more comfort to your feet, and with two sizes for the boot opening in regular and extra wide, you can find a fit perfect for you. Inner zip makes them a cinch to get on and off!

Cost and Value
One of the most budget friendly options on our list, the Dream Pairs OTK Slouchy will keep you looking trendy and help you keep warm. Versatile with its options of wearing low or high, and smart design to help keep the boot up as well as the right fit for you, it’s sleek look is sure to have you out and about looking good!



Adjustable Tie





Narrow Calf

7. Chippewa 6 Lace Up

7. Chippewa 6 Lace Up
Want something a bit rugged looking, but still stylish enough to wear out for the evening? Chippewa’s 6’’ Lace Up boot is handcrafted quality at its best. You can sport the American Flag lace pin as well to show some patriotic support, or just remove if it’s not your style. But, the rich leather look combined with comfort and Vibram outsole make this boot one in the running to consider!
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Quality Make
Burnished leather creates the uppers of the 6’’ Lace Up, with logo at the side, and an American Flag lace pin for patriotic adornment. Lace-up closure features D-ring hardware, durable and able to give a snug fit. Within the book lies a cushioned insert which is removable should you prefer custom orthotics or insoles.

Vibram soles help give this boot an added security of traction in wet or slippery weather or surfaces, making sure you stay sure-footed. Grooved sole helps displace water when walking or out in the elements. Along with its great rugged look, the 6’’ Lace Up is also perfect for casual parties, work, or yard work.

Cost and Value
One of the pricier options on our list, the Chippewa 6’’ Lace Up is a quality constructed work boot, that keeps a rugged look paired perfectly with and antique kind of flair. Burnished leather makes these great for pairing with jeans, or for work when pair with heavy duty pants or slacks for the office. A great choice if you’re in the market for a new pair to wear at work that has some ‘off worksite’ appeal.

Embellished Laces

Six Inch Lace Up

Burnished Leather

D-ring Closure



Sole Durability

Arch Support Lacks

8. Lucky Brand Basel

8. Lucky Brand Basel
This is a little bootie that packs a lot of punch. With a modest 1.5” heel, it’s easily an everyday boot, and the side zip makes it easy to slip on and off. What sets it apart is the intriguing nature of its design, which allows for breathability as well as a unique look. Ankle booties like this model are perfect for office wear or even for after work activities taking place at a swanky lounge. No matter where you wear these, you’ll look on point. They’ll dress up any outfit, which is especially helpful given some autumn outfits can be drab if they’re only geared towards being functional.
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They come in many various designs for which the only thing in common is the quality leather upper and rubber sole. One pair may have dozens of tiny triangle cut outs that dot the entire body of the boot. Another may be entirely covered in paisley. One may have a soft metallic gold finish, while another will have a wild leopard print. There are classically demure options like black suede, or daring options like grey snakeskin. There is an option for every wearer, provided they can decide on just one.

One would ordinarily expect these sort of shoes to pinch your toes or possibly slice into your ankles seeing that the toe box narrows to a point. However, their leather upper is soft enough that it molds to your foot shape with little break in time. They have a stacked block heel that distributes your weight more easily, and a pull-on loop near the entry to the boot that, combined with the side-zip, lets you get them on and off without any fuss. They can be walked in for several miles without fatigue, but those with wider feet will feel discomfort until they are perfectly broken in.

Cost and Value
These will cost about average compared to the rest of the items on this list. Being that Lucky Brand is associated with all things Rock ‘n’ Roll, and that the brand is devoted to the pursuit of individual style and making customers feel authentic, it’s not surprising that they have the wide variety of design options that they do. Whatever aesthetic you enjoy, there’s a Basel boot for your taste. These are not advisable to be worn in harsh weather conditions or any climate that gets a lot of rain and snow.
  • Wide variety of designs
  • Comfortable
  • Modest heel
  • Side-zip
  • Good traction rubber sole
  • Show signs of scuffing after a few weeks
  • Not suitable for wear in rain and snow

9. Timberland Premium

9. Timberland Premium
Just as the classic 8 eyelet Dr. Marten’s boot found its way onto our list, so too does the Timberland that started it all. Timberland footwear is known for their quality and their rugged appearance that can stand up to the elements coast to coast. The Timberland 6” Premium Waterproof Boot is made entirely from leather with a padded collar, lace up vamp, and has a rubber sole with thick tread. It will get you through the slushy streets of NYC in October and crunching over the falling leaves of CA in November.
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Made to Last
Favored by everyone from construction workers to rap artists, Timberlands are renowned for their durable exteriors that can take a beating. They have a tread that provides excellent traction on a variety of terrain, and the use of the same leather materials around the entire body of the shoe ensure that no portion of it wears down faster than the other, which can be the case when synthetic blends are used.

Removable Insole
They have a removable insole that allows for comfort customization, and the extra padded portion of the collar is robust enough so that the ankle doesn’t get chaffed where it touches the shoe. This is particularly handy if you plan on wearing your Timberlands for prolonged periods of time. The stitches don’t wear out along the inseam of the heel, since it’s made out of one solid piece of leather.

Cost and Value
In 1973 Timberland introduced its first ever waterproof boot, and they have been in production ever since. Known to represent quality materials, craftsmanship, and superior protection against the elements, their footwear represents a commitment to the outdoors and their customers that enjoy them. Though they can be pricey, it's well worth the investment considering the superior performance you'll get out of them well into the winter.
  • Removable insole
  • Waterproof
  • Padded collar
  • Quality leather
  • Thick tread outsole
  • Run small
  • Will show signs of wear

10. Vince Camuto Felana

10. Vince Camuto Felana
The Felana is a boot made to make legs longer, sleeker, and have heads turning with it’s long faux lace up and sexy heel appeal. Vince Camuto out-does it with this suede beauty, and keep in trend fashions for 2018 rocking with the lace up detail, plush black suede, and knee-high styling. A chunkier block heel makes these great for dancing or walking about town in the evenings, and the Felana can work great when paired with shorts, skirts, dresses, or jeans!
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Sometimes, knee highs with heels, although quite catchy, can only be worn for one or two hours before your feet start to get a bit sore. The Felana helps keep foot pain away by keeping a chunky heel to the boot, which not only is trendy for 2018, but distributes weight better. You’ll be able to wear this pair out for dancing or walking about town, or even to work when paired properly with jeans or asymmetrical skirts.

Sleek Suede
Keeping on trend again for autumn of 2018, soft, supple suede makes the uppers of this stylish sexy boot, and gives some flexibility to fit. A faux lace up vamp hides the fact these are pull ons, but gives them some added appeal and flair. A padded footbed helps keep you comfortable with each step, and a synthetic sole maintains good traction.

Cost and Value
While the Vince Camuto Felana may be one of the most expensive on our list, it’s one the sleek, sexier options of a knee-high boot for the season. Keeping on trend with its suede look, faux lace up, and chunky heel, this boot is sure to have heads turning. Versatile enough to pair with dresses, skirts, or jeans, as well as being comfortable, and they may just be your next favorite pair!


Soft Suede

Faux Lace Up

Brand Name

High Boot



Run Small and Narrow

When the season’s change, so must your footwear. Shorter days, colder air and more precipitation all mean that it’s finally time to put away your open-toed shoes and lightweight sneakers in favor of some warmer footwear with Thinsulate liners and over-the-knee coverage. This list proves that comfort and style can pair very well with functionality, allowing you to have a pair of autumnal footwear that will not only keep you warm and dry but will also look good, whether in a casual, dressy or professional environment. Depending on your needs and the price range you want to shop in, you can opt for features such as extra traction for when you’re out raking leaves, complete waterproofing for places that get wetter during October and November, or a higher shaft for added warmth. Some of our favorite ones will even combine more than just one of these features, making them the perfect choice for versatile use no matter the weather conditions. With this buying guide, you are sure to have plenty of information about a variety of options that will help you make an educated purchase. In case you find you need any additional information, make sure to read up on our Criteria for Evaluation, as well as the Frequently Asked Questions section at the end of this article.


Criteria Used for Evaluation

A woman throwing up red and orange leaves in autumn

Material (Waterproofing)

Unsurprisingly, one of the most important features you want to look for in your next pair is waterproofing. You may be surprised how few makers will produce footwear that is both warm and can keep water outside, making shopping for a good pair of autumn footwear a task much harder than it should really be. If you live in a climate that sees any level of precipitation during the months of October and November, you need to make sure that the ones you choose will be up to the task of keeping you dry and comfortable.

One of the things that will influence the way it performs in wet weather is the material it is made out of. Most companies will make autumn footwear out of leather, seeing that it is a great material that is both stylish and functional, and it provides the wearer with unique comfort and plenty of wear time. However, one of the downsides of leather is the fact that it’s not waterproof, and can even be damaged when exposed to rain or snow. If you have chosen to purchase leather ones, make sure to treat them with a water-repelling agent that will not only keep you dry but will also prolong the life of your shoes.

Rubber rainboots are another excellent option for autumn, seeing that they are completely watertight, and you can rest assured that you can go through any puddle without fear of ending up soaked. However, they do have two downsides. One is related to warmth, as a great number of rubber ones are not insulated, meaning that they will work better for mild climates with heavy rainfall. The other one is the fact that rubber footwear is not breathable, and can become quite the breeding ground for bacteria and odor, especially if you spend a lot of time wearing this type of footwear. This means that rubber rainboots are not suitable for everyday wear, and you should only opt for them if you already have a pair that will do well on dry days, and will provide you with a warm but breathable fit.

Last but not least, you could opt for one of the techier models on this list, and go for a pair of shoes that are weathertight, have a gore-tex lining or that are seam sealed. Having these options will ensure that your pair has an outer that looks good, just like any other pair of shoes, but your feet will get the benefits of complete waterproofing, no matter the situation.



It is very important to consider the weight of your next pair, especially if you intend to spend a whole day in them, or if you are purchasing them for outdoor, hiking use. As a rule, the heavier a pair of shoes get, the more tired you will feel after having worn them for a few hours. So, for example, if you are in the market for a pair that you can wear to your job, you need to consider the fact that you will be spending over 8 hours wearing these shoe, making it really impractical to choose something that is clunky. Instead, try to opt for footwear that is as light as possible, but still offers the features you need, including a lining to keep you warm and weatherproofing to prevent you from having to walk around with damp socks all day.

While some people will need the protection of a higher shaft, they can be a great choice when it comes to weight, seeing that they are often made as ankle booties – giving you the perfect combination of protection and warmth without the unnecessary, heavy addition of a high top that can be saved for winter and colder days.



While durability and a cheap price are not always mutually exclusive, it is important to decide how much you are willing to pay based on how long you intend to wear them. Some people prefer spending less and purchase new ones every few months, while others will be willing to pay a higher price and have a pair that will last them a lifetime. Whichever your preference is, there is a couple of things you need to consider. One is the reliability factor of your chosen autumn footwear. While you may be tempted to go with the least expensive item you find, it’s important that you don’t waste your hard earned money on something that will fall apart or start leaking after just a few wears. On the other hand, you might find that investing a couple hundred dollars could actually buy you a pair that you will wear for the next twenty years.

Whether you are shopping for just one season or for a lifetime of wear, it’s good to consider the reputation of the brand before making your final choice. For example, models made by Red Wing, Wolverine, Timberland and L.L. Bean are all excellent choices as they make footwear that is ready for any challenge, providing you with plenty of wear time. Dr. Marten’s is also excellent, as are brands that make footwear for the Armed Forces such as J. Crew and Alden.

A brown cowboy hat, a cup of coffee and autumn leaves laid out on a wooden surface

Climate Protection

Leather is versatile and looks great on anything people can wear. But water, snow, and salt are leather’s enemy as these tend to age it too quickly and turn it into a cracking, unrepairable mess. Basically, what this means is that leather is not the best choice of material to wear out in places where there’s more snow than solar panels. You can preserve said leather by cleaning it with saddle soap. Or you can buy some from any sporting goods and cold weather clothing store, that have been made from the ground up to survive in the cold. Waterproof membrane, Thinsulate, leather mixed with silicone during the tanning process, or even a mixture of these choices. Be prepared to spend a lot of money if you want long-lasting and anti-weather ones, though, seeing that high performance such as this can set you back quite much. It’s a great idea to look at brand reputations for making high-quality weatherproof footwear, and starting with names like Baffin, Sorel, Woolrich, KEEN, and Kodiak is a good option.


Ground Traction (Thickness Of Tread)

While some places get a dry but chilly autumn, others will have to deal with plenty of rainfall that makes life (and choosing footwear) quite difficult. One of the most important things you need to consider is the outsole they are made with. Leather will not perform well on wet or slippery surfaces, and it is your best bet to avoid it. A rubber outsole will give you more grip, so choosing a pair of shoes that has a rubber sole is a safer bet. In addition, rubber and rubber compounds will do well with wetness, snow, and can even be used in the workplace if you need to walk on oily surfaces. Furthermore, the rubber will prove to be more flexible and will give you the benefits of better shock absorption and cushion, overall improving your wear experience. Materials that also work well for the autumn season include nitrile cork, polyurethane or even some combinations that include EVA foam.

It’s also important to consider the pattern on your outsoles, seeing that a flat surface will generally not do as well as one with more lugs. If you need to walk on wet pavements, in muddy conditions, or if you want to extend their use into the winter season when you’re looking at snow and ice underfoot, it’s better to opt for a shoe that has more grooves on the bottom, allowing you to confidently take each step without having to worry about slipping and hurting yourself.



There is footwear that is drab and boring and is made only with productivity in mind. And then there are others that look so cool and stylish that you want to wear them even when the cold weather has passed. It’s a great thing to be able to choose a pair of shoes that are as versatile as possible. This not only relates to style – as we all want a comfy pair of shoes that look good both with a casual as well as a more dressy outfit, but also to functionality. The perfect ones will perform just as well in rain as in dry weather and will be comfortable to wear in both cold weather and on those days when the sun decides to shine through the clouds. If you manage to find a pair that can even work in the summer, such as the Ariat Heritage Roper, you can consider yourself to have made a really great purchase.

Another thing to consider is that they offer a versatility of use outside the autumn season, and if you’re someone who needs a pair of shoes for those long hikes, rock concerts or even a good pair of protective work gear, they will prove to do well on these occasions.

A fall road lined with trees with red and orange leaves in King City


Ultimately, a good pair of shoes is only worth as much as the benefits they provide you with. While durability, waterproofing, traction, versatility, and warmth all come into play, you still need to consider what makes a perfect pair perfect for YOU. Some people might prefer a thigh-high style for aesthetic reasons, while others appreciate it because of the added warmth they supply. Designers and popular shoemakers have wised up with their potential customers, recognizing the need for footwear that will both look good and perform well in certain types of situations. A great example of this is calf width and how it relates to the construction, as well as the need for more orthopedic features for maximized comfort and support. Having zippers on tall, over-the-ankle models was probably the best idea ever; getting rid of the time it takes to fit the feet into them whilst avoiding the moving of cushions on the insoles. Amazingly, great looks don’t need to be compromised in exchange for functionality, which is our definite favorite part of each and every one of our top choices. There are not many things that are as great as getting to wear shoes that match your wardrobe to a tee, yet can still keep your feet dry, warm and protected.



Whether you’re strolling through the woods with your loved one, or you’re walking through the rain between a corporate office and the light rail station, wearing a pair that can keep your feet dry and comfortable can be worth every dollar or extra dollar spent. Cushions that circumfuse around the bottom of your feet, materials around the ankle that give you support and don’t cause any chafing, the use of Thinsulate and waterproof material in them – these are all crucial aspects of any pair of footwear, especially if you have to wear it for longer periods of time. Based on your needs, possible foot conditions and preferences, you can actually choose a style that will work best for you, keeping you both pain-free as well as happy knowing that they match your outfit perfectly.



Unlike the earliest individuals who inhabited the same spaces you do today over hundreds of years ago, you have the advantage of facing cruel winters and bitter rain storms knowing that you’ve got the footwear that will keep you nice and warm. While traditional footwear used wool and animal hide, which are widely used today as well, you have the advantage of available technology (despite its side effects on the environment) to create insulation. Like 3M’s “Thinsulate” – a thin and highly insulating fabric made from polypropylene fibers. 3M had trademarked that name and it can be found in most autumn and winter ones. A few other companies would try either to create their own style of insulation or will use straight-away polyurethane foams which also provide good protection from the cold.

Frequently Asked Questions


Q: Should I avoid “cheap” ones? And where should I buy them?
A: You might want to avoid buying ones from any well known big-box stores, seeing that those run the risk of being ill made or hurriedly-manufactured. Even if you’re only using them for a year, don’t be afraid to spend more money on something that can last you more than just a season. Do some research; visit the multitude of sporting good stores, specialty shoe stores, “premium outlets,” and online company-based shops. Even if your favorite music artists promote certain brand named ones, there might be something better on the other side of the noise.

Q: Zippers or laces?
A: Remember that one Levi’s pants commercial where two guys were using the bathroom stalls after snowboarding? The words “Zippers Freeze” came up and then one of the guys were screaming? Fortunately for people today there’s “non-freezing zippers,” a piece of technology that’s used by the Armed Forces. However, laces have always been the definite way to go over using zippers. (Velcro has also seen its use, but not so much.) For those who’d choose laces, there are several ways and styles to tie your laces. So, when you have the time, be adventurous and see how far you can go in style and functionality.

Q: How do you wear them with pants and with dresses?
A: While there isn’t any official “wrong way,” the “play of the game” is to make sure what you’re wearing doesn’t look too tacky or out of place. The type you wear at a punk rock concert or masquerade ball won’t fly too far at a convention center or large social gathering. The general idea, for those that go above the ankle and towards the knee, is to wear them with your pants tucked inside. If they don’t go far from the ankle, some people tend to roll up their pants legs to make cuffs, being sure they don’t hit the top of the booties. For dresses; the fashion tips of the day are 1) not to wear all black (because it’s dreary), 2) not to be afraid to show a little leg (even if you’re wearing stockings or thigh-highs), and 3) to lighten up and use a variety of colors.

Q: What are ankle models good for?
A: “Ankle Boots” are those that go up either around the ankle or about an inch over it. They’ve been around since the early 19th century and have been making a comeback because of their versatility. And while there have been some for men, the list and choices for women’s ones are much bigger than for men. A bit of advice here is not to wear ankle booties with heels that are too high or have a stiletto heel. It should also be noted that they should be avoided if you have bad or injured ankles. They might make these problems even worse.

Q: What are tall ones good for?
A: Like ankle ones, they can be worn for style points if done correctly. There are companies that make them work well as for the autumn (i.e. Hunter, Fergalicious, Bearpaw, Durango, Ariat, and Aerosoles). But the lot of them are created for fashion and not functionality which can cause some problem. One case is that the top is too wide and forms a gap around the thighs. So they end up moving around the legs as you walk. Another case is when the top lands on the thickest part of the thighs, thus making the legs look wider. They should fit snugly and comfortably around your legs. If your thighs are your “problem area” then you should opt for ones that reach up or over the knees

Q: Are combat/hiking/mountaineering/hunting ones good for autumn?
A: The simple answer is yes. All of those are made to keep your feet comfortable whilst in the most extreme conditions. With most users, lace hooks are preferred over closed eyelets as they make it easier to get your foot out if it gets injured. Whether you’re suddenly fighting rebel forces in some unknown land, travelling up and down a mountain, or laying low with your rifle in the hopes of getting your next week’s dinner, even for looking good on the busy streets of New York, they can be a great choice for autumn wear.

Q: …okay so what’s the difference between them?
A: Hiking ones are light and meant for traveling along rough terrains, woods, and fields. Mountaineering ones are heavier and have better-gripping outsoles. They’re obviously made for climbing mountains and near-vertical terrain. Hunting ones are specially created to keep your feet warm and dry while you’re hunting for game or waiting for it to appear; whether you’re out in the cold woods or snow, or out on the extreme prairie or desert. Combat ones are specially designed to keep your feet and ankles safe from sprains and other damage; keeping yours from failing on a mission or in the thick of a firefight.

Q: Are western/cowfolk and motorcycle ones good for the fall?
A: Those worn by cowboys and cowgirls have been the staple of the “wild frontier” and career that involves riding on horses. Of course, they’ve been specifically created to keep your feet and lower legs warm and secure. So wearing them during the cold seasons is a non-issue. In fact, it’s a little more difficult to wear them out in the heat. So it’s best to make sure your socks are able to take up a lot of sweat you’ll be producing. Motorcycle ones are specially designed for people who ride motorcycles. About half of them either have short laces or avoid them altogether (using either velcro or straps) because they’ll get caught in the engine parts. They have that unorthodox look of them, which makes them pretty cool, and they are still as functioning.

Q: What are Chelseas? Chukkas? Uggs?
A: Chelseas are elastic-sided, ankle-high booties. They appeared during the era of the United Kingdom’s Queen Victoria (circa 1876-1901) and took root in the country’s “mod” (modern jazz) scene. The Beatles (in 1961) wore them with tailored suits. Chukkas, (alias “desert booties” or simply “Clarks”) also had their roots in the UK. They’re lightweight and grippy, made of leather but with rubber soles and around 3 eyelets. And they were first seen on the British forces during the Western Desert Campaign of WWII. Uggs are unisex sheepskin ones that originated in Australia and New Zealand during the 1960s. They were worn by surfers for the warmth they gave their feet; being popular amongst surfers in Australia, New Zealand, and California. Uggs are still popular despite issues with animal rights activists, trademark disputes, and being tied to the unfashionable or social outcasts.

Q: Are those with wooden soles/heels any good?
A: Wooden soles and wooden shoes are not really a good idea. They are popular in places like the Netherlands, Sweden, and Japan. But wearing them is not good because your feet can’t get any feedback about the ground. They’re already on something solid, the wood itself. Plus they destabilize your foot arch and contribute to toe ailments like hallux valgus, bunions, tailor’s bunions, hammertoes, and claw toes. Wooden heels, however, are slightly better. Wide wooden heels to be exact. It’s important to have stable footing while you’re in your shoes; to make sure your ankles don’t roll or you don’t slip. Having rubber under the wooden heel can also help a lot.


When it comes time to clean your footwear, we have a guide for that.

If you need to repair a shoe, we have a guide for that too.

Is your current shoe causing blisters? Here’s how to prevent them.


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