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Best Men’s Ankle Boots For Rustic Vibes Reviewed

last updated Feb 06, 2019

The cold weather is slowly creeping its way in, and it’s time to say goodbye to casual sneakers and breezy sandals. Although, it might still be too warm to wear actual boots, so what are you supposed to do? Any style-minded man knows ankle boots are the solution. Crafted just right to keep you warm and fashion-forward no matter the occasion, ankle boots come in a variety of styles that are the upgraded version of your old-fashioned dress shoes.

No matter how peculiar your own fashion sense may be, there will be an ankle boot swank enough to make a statement with! We have collected some of the fanciest ankle boots found on the market today, and rated them in our helpful guide so you can discover just what you’re looking for!

In a Hurry? The test winner after 6 hrs of research

icon
Ted Baker Twrens
97.4/100 our score
Comfort
95
Materials
98
Style
99
Durability
97
Versatility
98
Ted Baker Twrens
Why is it better?

Wingcap Oxford Boot

Brogue Details

Textured Panels

Branded Grosgrain Tape

Ted Geometric Pattern

In a Hurry? Editors choice:
Ted Baker Twrens
Test Winner: Ted Baker Twrens
Researched Sources
9
Researched Sources
Reviews Considered
1180
Reviews Considered
Hours Researching
6
Hours Researching
Products Evaluated
10
Products Evaluated
Sorting Options
Comfort Materials Style Durability Versatility By Default
Rank
PictureProduct
Name
Rating
Shops
#1
The rating is based on the average rating (1-100) from all the criteria in which we rated this product.
97.4
Comfort
95%
Materials
98%
Style
99%
Durability
97%
Versatility
98%
Price Comparison Last Updated (20.04.19)
$132.49
#2
The rating is based on the average rating (1-100) from all the criteria in which we rated this product.
94.2
Comfort
93%
Materials
95%
Style
96%
Durability
95%
Versatility
92%
Price Comparison Last Updated (20.04.19)
$299.99
#3
The rating is based on the average rating (1-100) from all the criteria in which we rated this product.
91.2
Comfort
89%
Materials
93%
Style
90%
Durability
95%
Versatility
89%
Price Comparison Last Updated (20.04.19)
$319.98
#4
The rating is based on the average rating (1-100) from all the criteria in which we rated this product.
90.2
Comfort
89%
Materials
91%
Style
92%
Durability
89%
Versatility
90%
Price Comparison Last Updated (20.04.19)
$465.95
#5
The rating is based on the average rating (1-100) from all the criteria in which we rated this product.
86.4
Comfort
87%
Materials
88%
Style
88%
Durability
84%
Versatility
85%
Price Comparison Last Updated (20.04.19)
#6
The rating is based on the average rating (1-100) from all the criteria in which we rated this product.
85.2
Comfort
86%
Materials
85%
Style
84%
Durability
86%
Versatility
85%
Price Comparison Last Updated (20.04.19)
$99.95
#7
The rating is based on the average rating (1-100) from all the criteria in which we rated this product.
83.6
Comfort
85%
Materials
83%
Style
81%
Durability
84%
Versatility
85%
Price Comparison Last Updated (20.04.19)
$72.03
#8
The rating is based on the average rating (1-100) from all the criteria in which we rated this product.
81.6
Comfort
82%
Materials
80%
Style
83%
Durability
83%
Versatility
80%
Price Comparison Last Updated (20.04.19)
$364.00
#9
The rating is based on the average rating (1-100) from all the criteria in which we rated this product.
75
Comfort
76%
Materials
73%
Style
75%
Durability
77%
Versatility
74%
Price Comparison Last Updated (20.04.19)
$139.95
#10
The rating is based on the average rating (1-100) from all the criteria in which we rated this product.
72.4
Comfort
74%
Materials
72%
Style
74%
Durability
70%
Versatility
72%
Price Comparison Last Updated (20.04.19)
$100.00
In Depth Review Top 10
  • Ted Baker Twrens
  • Belstaff Stockwell
  • Red Wing Heritage
  • Tricker's Stow
  • Timberland Brook Park
  • UGG Dustin
  • Clarks Vargo
  • Wolverine 1000 Mile
  • Dr. Martens Church
  • Steve Madden Blackburn
Table of contents
  • Criteria Used for Evaluation
  • Other Factors to Consider
  • Frequently Asked Questions
  • Sources

Top 10 Picks

1. Ted Baker Twrens

The rating is based on the average rating (1-100) from all the criteria in which we rated this product.
97.4
Ted Baker Twrens
Comfort
95
Materials
98
Style
99
Durability
97
Versatility
98
best offer for today
$132.49
Pros:

Wingcap Oxford Boot

Brogue Details

Textured Panels

Branded Grosgrain Tape

Ted Geometric Pattern

Cons:

Narrow

The Oxford Boots are the ideal formal pair that can keep you both warm and fancy! The Twrens has a leather upper, with a lot of going on there! First, we have the brogue details, that dance around the edges of the wingtip detail and the vamp. The change of leather texture signifies a new era of tasteful shoes and fancy parties! The textured panels combined with the accent stitching is what makes this pair fit for the most extravagant of events.

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The padded collar makes it easy for your ankles to survive the break-in period and cushions you gently. The cozy sock liner eases every step of the way and makes it possible to enjoy the beauty of these boots all day long. The sole is molded, and it features a geometric finish, offering a trendy yet durable solution for stylish trendsetters everywhere.

2. Belstaff Stockwell

The rating is based on the average rating (1-100) from all the criteria in which we rated this product.
94.2
Belstaff Stockwell
Comfort
93
Materials
95
Style
96
Durability
95
Versatility
92
best offer for today
$299.99
Pros:

Vintage Style

Calfskin Suede

Low-cut Profile

Molded Footbed

Stacked Short Heel

Cons:

Pricey

The luxury British heritage brand gives us a taste of their medicine with the Stockwell lace-up boots. Every pair is handcrafted, and this one is no exception. Supple suede was stitched together to breathe life to this unique vintage boot. The low-cut profile lets the world glimpse at your socks, so if you want to explore silly patterns and crazy colors, now’s the chance! The metallic eyelets wrap around the round laces, that is more than just a fashion detail.

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Rounded toes remind us why we like the extra wiggle room, as there will be nothing there to pinch or irritate you. The footbed is molded, giving you support just where you need it. There will be no bulky cushions here, only sublime comfort! The short stacked heel gives you much-needed arch support and a little pizzazz to your gait! The Stockwell is complete with the scintillating metal logo attached to the soles.

3. Red Wing Heritage

The rating is based on the average rating (1-100) from all the criteria in which we rated this product.
91.2
Red Wing Heritage
Comfort
89
Materials
93
Style
90
Durability
95
Versatility
89
best offer for today
$319.98
Pros:

Supreme Durability

Copper Rough Tough Leather

Moc-toes

Traction Tred Outsoles

Nickel Eyelets

Cons:

Stiff

This super chunky boot is a handsome solution to our smart casual attire problems. Their leather upper in a palette of various colors, so there will be plenty to choose from! The moc-toes accentuate the bulky silhouette and help reinforce the construction, making this pair a lasting one. They have triple stitches, and a Goodyear welt, so test these out on any terrain as much as you like and be surprised by their remarkable endurance!

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The Nickley eyelets will never rust over and will look shiny and clean for a million years. The insoles are leather as well, wicking away moisture and keeping you dry and happy. The outsoles have a crepe wedge, and a traction tread so you’ll get plenty of arch support and grip!

4. Tricker's Stow

The rating is based on the average rating (1-100) from all the criteria in which we rated this product.
90.2
Tricker's Stow
Comfort
89
Materials
91
Style
92
Durability
89
Versatility
90
best offer for today
$465.95
Pros:

Heavy Brogue Details

Storm Welt

Huge Pull-tab

Derby Boot Style

Half Bellows Tongue

Cons:

Tight Fit

Stay safe in the cold weather and keep up with the latest fashion trends with the Stow wrapped around your feet! One of the first things we should mention is the heavy brogue details. In case you don’t know, brogue details are the various circular laser cut-outs scattered all around the uppers of many trendy shoes, in this case, the upper of the Stow. On the front, they fold out and accentuate the toes, while the rest of them follow along with the lines of the stitching sharpening their lines. A wingtip is also present, also hugged by brogue details. They are 100% leather, giving you sublime comfort and a refurbished look.

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Now let’s talk about their color. The colors might be all quite neutral and calm, but you’ve got virtually every shade of brown, so you can match it up with a lot of bright hues. Their design helps you put them on easier while simultaneously improving their fashion. Derby boots are more casual by nature, but since the appearance of this one is so classy, they might even fly for formal situations. The half bellows tongue is attached tightly, keeping it in place and your skin irritation free. A storm welt strengthens the construction, so when the outsoles get worn down eventually, you will be able to replace them.

5. Timberland Brook Park

The rating is based on the average rating (1-100) from all the criteria in which we rated this product.
86.4
Timberland Brook Park
Comfort
87
Materials
88
Style
88
Durability
84
Versatility
85
best offer for today
Pros:

Smooth Leather Upper

Blind Eyelets

Contrast Stitching

Anti-fatigue Technology

Gripstick Soles

Cons:

Soles Separate Near Toes

Runs Narrow

Timberland is a company known for creating gorgeous boots, in the signature yellow color. Although that kind of boot is their most popular one, we shouldn’t look over their other boots, like the Park, a super fancy Chukka boot! These versatile babies are premium leather, with a smooth finish and gentle gloss, giving them a formal vibe. A handy pull-on ribbon sits on the heel counter, meaning there will be no more struggle to pull them on. Four blind eyelets make it easy for the slim laces to wiggle through, enhancing their clean lines.

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The contrast stitching helps hold the boot together, and also adds just the right amount of detail to this sharp pair. A little leather accent sets the border between the heel and the upper, and adds a dash of color to the solid black or brown, depending on what you choose. The heels have a leather welt, reinforcing their construction, even more, making them a super durable pair.

Environmentally friendly-linings caress your feet and help recycle plastic, since they are 50% PET! The anti-fatigue comfort technology keeps you well-rested and cushioned, eliminating the possibility of pain or aches ever knocking on your door. The arch support is also something that you should not take lightly, as they will brace you for any impact or shock the ground might create as you go about your day. Gripstick soles fashion peculiar patterns, a unique L7 lug design, that make it easy to dance in the rain and walk vertically!

6. UGG Dustin

The rating is based on the average rating (1-100) from all the criteria in which we rated this product.
85.2
UGG Dustin
Comfort
86
Materials
85
Style
84
Durability
86
Versatility
85
best offer for today
$99.95
Pros:

Earthy Colors

Chunky Outsoles

Wide Boot Opening

EVA Insoles

Treadlite Outsoles

Cons:

Narrow Toebox

UGG is best known for creating super comfy casual boots, but they can surely create a marvelous pair of fancy boots, and the Dustin proves that effortlessly. The soft suede upper comes in four Earthy colors, great for many various clothing combinations.

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The different upper colors feature the chunky outsoles in colors that accentuate them the best, so no matter what you choose you’ll always look dashing. The boot opening is wide enough for the highest of arches, and if that doesn’t work, there are always laces present to help you transition into them without any issues. The insoles are EVA, which is a superior material that provides great support, enough shock absorption and is light enough so you don’t get tired so fast. The outsoles are Treadlite, their unique innovation for outsoles with just the right amount of grip, weight, and traction to propel you into a perfect life!

7. Clarks Vargo

The rating is based on the average rating (1-100) from all the criteria in which we rated this product.
83.6
Clarks Vargo
Comfort
85
Materials
83
Style
81
Durability
84
Versatility
85
best offer for today
$72.03
Pros:

Different Leather Colors

Red Color Details

Cushioned collar

Removable Ortholite Footbed

One Regular Eyelet

Cons:

Sizing Is Off

Clarks might not be the first company you’d think of for stylish ankle booties, but trust us when we say they’ve got an ace up their sleeves. The Vargo fashion boot has a lot to offer, and you’d be silly not to take it up! They have a leather upper, constructed out of bits that vary in color and shape, giving them a slightly formal vibe. A super chunky stitch connects the strip that stands out, acting both as a statement and as additional support.

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A red strip runs along the border of the outsoles, while red stitches peep through the opening of the boots, settling on top of the tongue. The collar is cushioned, so you can rest easy knowing nothing will cut into the skin of your ankles and cause discomfort. A reinforced heel counter lengthens their lifespan and keeps you blister-free. A removable ortholite footbed sits on the inside, working harmoniously with the Cushion soft technology to provide you with all-day comfort and pain-free life. The eyelets might look regular, but only the first one is visible, while the rest are blind - a very bold urban detail. The outsoles are chunky and help keep you safe from falling down.

8. Wolverine 1000 Mile

The rating is based on the average rating (1-100) from all the criteria in which we rated this product.
81.6
Wolverine 1000 Mile
Comfort
82
Materials
80
Style
83
Durability
83
Versatility
80
best offer for today
$364.00
Pros:

Handcrafted

Vibram Rubber

Goodyear Welt

Stacked Leather Outsole

Cons:

Narrow

Handcrafted in the USA, the iconic 1000 Mile boot is a pair we had to include in our guide. This brilliant combination of style and function is what we all need hugging our feet. The full-grain leather upper ensures maximum durability and supreme comfort. The flat waxed cotton laces stay in place and strap your feet in. This updated model of the original 1000 boot features Vibram rubber, a highly functional and durable kind that will surely keep you safe and sound.

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A Goodyear welt holds their construction together and allows you to replace their outsoles once they get worn down. There’s no doubt that you will have this pair for a long time! This welt is also flexible just enough to support your feet the right way. A stacked leather outsole keeps you warm and has enough grip to keep you upright even on the slickest of surfaces!

9. Dr. Martens Church

The rating is based on the average rating (1-100) from all the criteria in which we rated this product.
75
Dr. Martens Church
Comfort
76
Materials
73
Style
75
Durability
77
Versatility
74
best offer for today
$139.95
Pros:

Various Colors And Details

Air-cushioned

Slip Resistant

Doc Marten DNA

Monkey Boot

Cons:

Heavy

Tongue Slips Around

One more iconic British brand brings us their version of ankle boots: the monkey boot, a sturdy yet classy pair. They are 100% leather, but their appearance varies slightly depending on the color of your choice. The tan boot is a classic, mature pair, with a solid look and intricate stitching. The light grey one, or mare, is suede, with a fizzy finish and a rich look. Now the black one is more fashion-forward, with a stitch splitting down the two different sides - a completely smooth, solid black side, from the lower part riddled with a million little holes, acting as eye-catchers. And last but not least, the one colored in oxblood has an almost plastic-like look, thanks to the brilliant shine and the yellow stitching.

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The rest is the same for every boot, including their construction. They all have five eyelets, through which slim fabric laces pull through, helping you achieve a secure fit. The sole is air-cushioned, a staple with many Doc Marten shoes, and it does bring a lot of comfort with it. Every pair has the classic doc DNA - the yellow stitching, the AirWair pull tab, and of course, the Goodyear welt, which is somewhat responsible for their well-deserved fame and icon status. The outsoles are chunky, rubber and slip-resistant.

10. Steve Madden Blackburn

The rating is based on the average rating (1-100) from all the criteria in which we rated this product.
72.4
Steve Madden Blackburn
Comfort
74
Materials
72
Style
74
Durability
70
Versatility
72
best offer for today
$100.00
Pros:

Double Elastic Panels

Chelsea Boots

Earthy Shades

Leather Strip Under Gore

Cons:

Not Too Durable

This famed British designer will stop at nothing to bring you the affordable, yet comfortable and trendy pair, and the Blackburn is one of them. Chelsea boots have always been a fashion staple, both for men and women, since their effortless style and cozy comfort make everyone ecstatic. Their suede upper comes in four refined colors, their hidden shades brought out by the brown elastic gore. The lack of details is what sells them as a formal option, but that doesn’t mean they won’t pass for casual events as well!

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The double gore panels stretch out as your feet make their way in, negating the need for zippers or laces, so say goodbye to extra details. A leather strip covers the stitches under the gore and contrasts the soft suede with its shiny surface. A short heel gives stability and balance, while the finish makes them look stacked without the extra weight wood tens to bring with it!

Criteria Used for Evaluation

Comfort

Just like any other shoe, ankle boots should be comfortable. You might be tempted to sacrifice comfort in order to look sharp, but we urge you not to. Comfort is very important, and proper footwear will make sure you don’t suffer the consequences of ill-fitting footwear. Yes, that boot might look out-of-this-world, but it tires you down and causes blisters, and why should you suffer through that? Of course, some troubles always arise when you first buy the pair, since you’ll probably need to break them in. But how can you be sure that the problems you are experiencing are because the shoe is new, not because it was badly made?

It’s quite simple - if the problem persists, blame the badly made pair! You should rule out everything else first though. Make sure you know your size, including whether or not you need a wider fit, and take the sensitivity of your feet and existing health problems into account too. If you suffer from mild or more serious health problems, prepare with good orthotics and look for a pair that is more suited for your needs. There is no need to sacrifice beauty either! Plenty of smart and elegant pairs exist out there that look mind-blowing, and are comfy too.

But, when people say comfort shoes, you immediately imagine grandpa sandals and bulky unsightly footwear right? This is not what we’re about here, and we work hard to show you that you can look AND feel good at the same time! Look at Timberland boots, for an example, - yes, they do make work boots, but they have plenty of lookers too. And, all of their lookers are fitted with anti-fatigue comfort technology, and as the name suggests, it will help you feel cozy and well-rested. They cushion the collars, the insoles, make proper midsoles with good support, and quality outsoles that will not let your feet slip around and feel sore. Clarks is also one company we feel should be mentioned. Their cushion soft technology helps keep you happy and healthy and makes the days so much easier. You will need to invest more to get a pair that is just right, but think about it this way - you will pay more, but you will look and feel much better too!

If you already decided to go for a less than a comfortable shoe, then there are a few tricks that can help you make them just a bit cozier. Stretch them out as much as you can! Put an ice pack in them and stick them in the freezer. As the water expands while it chills over, the material will expand as well, and the lower temperature will help them remain stretched out. Or, you can put on thick socks, grab a hair dryer and heat them up - the same thing will happen.

If none of these things help, just take them to be professionally stretched out! Ankle boots also tend to cut your ankles, or the skin around them to be precise. If this is happening, try adding an insert to lift your feet up a little bit. But then, the top of the shoe squeezes you down! Nothing a little bit of stretching can’t fix. Since most ankle boots have eyelets, sometimes a boot with scratchy ones will appear. Don’t suffer the irritation and cuts, just tape over those bad boys and you’re good to go! And, don’t forget that arch support! Add an insert with arch support if this is a troublesome area for you.

Materials

Choosing the right kind of material to create footwear does wonder to a pair. If you care about the way you look, then you probably already know just how important proper material is. The type of upper a shoe has can make it casual, or it can make it fit for a fashion show. When it comes to boots, there is not much variety. Since they are meant to be worn when the weather is colder, the obvious choice here would be leather. Textile is too thin and will not keep you warm, and quite frankly, it would probably look silly on boots! But if it’s combined with other materials it can look great.

Leather was always considered to be one of the best choices for footwear, no matter the type. It’s natural, protective, and durable, so you will have a proper shoe for a long time. And the best part is, leather has a certain tone it brings with it, making anyone appear refurbished and sumptuous. This material works the best when paired with dressy boots and evening wear since it will fit there like a glove. Also, leather is quite versatile - it does not take on color very well, so you will usually end up with brown or black uppers.

These two colors blend in with anything you throw at them, and since leather by itself is very versatile, you will end up with something you can wear to a million different events. Is it raining outside? It doesn’t matter, leather is there to keep you dry and fresh! Has the sun played us a fool and showed its face too early? Do not fret, leather acts like real skin and will keep you sweat-free and odor-resistant! The leather is quite heavy though, so it might take some time for you to get used to the eight, and you will need to spend a considerate amount of time breaking leather in.

And that’s where suede comes in! Suede is also leather, just without one important layer. The absence of this layer reveals the surface we all know suede best for - soft and luxurious, fuzzy and sophisticated. Suede looks great on boots, and when combined with the right details and decorations, be sure you’ll look like a fashion icon! This linty upper does have drawbacks though; it’s not so durable, and it’s very hard to clean.

Style

Of course, when you look at ankle boots, one of the very first things you will consider is their style. And we’re not talking just about how good they look, but about what they look like overall. Ankle boots come in a huge variety of styles, all with a different story and all meant for different events.

One of the most popular styles of ankle boots is the Chelsea boot. What makes them stand out is the lack of laces and that dual panel elastic gore on the sides. The lack of laces makes them look sharp and clean, fit for formal occasions.

The gore panels help you put them on easily since the lack of laces would make that troublesome. Interestingly enough, Queen Victoria was the one who is credited for the design, and the Beatles also loved their style. They are popular as riding and working boots as well since they offer a lot of flexibility thanks to those elastic panels.

Chukka boots also make a good fashion detail. These boots are almost always made out of leather or suede. What makes them special is their ability to blend in with a lot of outfits you might procure! They are a great match for both casual and smart situations, but they are not too formal since their round toes make them look a little mellow.

The Oxford boot should also be mentioned. They are the origin of Oxford shoes, and as such appear imposing and cultured. They emanate sophistication, and should not be worn with anything that can’t match their level of grace. These boots are what the perfect gentleman needs to have in their closet (at least when the weather gets colder, for everything in between turn to your Oxford shoes)!

Durability

Impeccable style is eternal, and the shoe that brings that with it should also last forever. Well, nothing really lasts forever, but why should you have a pair that lasts only one season? If you’ve found that perfect boot and want to enjoy its company for as much as possible, it’s only logical to search for something that will last for a long time! We all know how difficult it can be to find footwear that both looks and feels good, and when you do, you can only hope it will hold on.

Buying a proper pair will, without a doubt, mean that you’ve got a long partnership ahead of you. Since ideal ankle boots are leather, and leather is considered to be the most durable material out there, you can rest easy knowing you won’t need to replace them soon enough. Although, watch out for the grade of leather and the way it was put together too! Top-grain leather lasts the most, while bonded leather falls apart almost as fast as textile does. And, it looks patchy - no one wants to look like they’ve found their shoes behind a dumpster!

Poor stitching or bad glue also won’t help your case. Besides being short-lived, bad stitches also impact the way you appear, and excess glue on the sides or outsoles affect your style, preventing you from shining like the true star you are. Inspect the boot closely, and keep the construction in mind; this will ensure you’ll get something you will be able to wear for forever and a day.

Versatility

A versatile, quality shoe is something we all dream about. Who wouldn’t want to invest in footwear that will be able to complement most of their wardrobe? A good looking boot should make any outfit stand out. But what exactly makes a pair versatile? Well, for starters, their style. If you’ve got a plain pair of Chelsea boots for an example, you are set with a pretty flexible item. But if you’ve got a super flashy boot adorned with many details, you won’t have so many options. In fact, you might only be able to wear just one combination like that! So if you’re on a budget, find simple, yet tasteful shoes.

The color is important too! Calm colors like tan or black work with many outfits and patterns, since they are the perfect backdrop. Vivid colors and wild patterns will never be versatile since they are a statement piece by themselves. So, if you’re looking for a pair that will go along with various clothing combinations, keep these things in mind!

Expert Interviews & Opinions

Most Important Criteria (According to our experts opinion)
Sort criterias acording to:
Experts Opinion Editors Opinion Users Opinion By Default
Click on a to rate the most important criteria:
#1
Comfort
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#2
Materials
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#3
Style
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#4
Durability
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#5
Versatility
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Expert Tip

Comfort is an important factor when it comes to fashion. Let’s just say you will never look good if you struggle to walk or stand right! Comfortable footwear will give you confidence, making sure you achieve everything you set your mind to since there will be nothing left to bother you!

Expert Tip

Struggling to clean your suede pair? Doing it wrong can seriously damage your boots, rendering the pair useless! But if you clean them properly, they will last a long time, all the while looking great. Think ahead of time, invest in a good suede protecting spray. And avoid wearing light colored suede in the rain! Water leaves gnarly stains, and we don’t want that. Get yourself a suede-cleaning brush, or an eraser made for suede uppers, which works great for any type of stain. If the stain is really stubborn though, use vinegar - pour it on a cloth and lightly dab the affected area, and then wipe it dry!

Fun Fact

The Beatles also loved the Chelsea boots! In fact, they loved them so much that they incorporated them into their iconic style. But, they did make a few changes - the toes were squared off, and a Cuban heel was added, giving the wearer more height. This redesigned shoe is what we know today as a Beatle boot! If you also wish your Chelsea boot gave you more height, look for this style instead!

Other Factors to Consider

Bottom Line

Ankle boots are something everyone who cares about style (and warmth) should have. Their length keeps you warm, and their style makes you fashionable. As you can see, the world of ankle boots varies a lot, so you won’t be left empty-handed. The style options are diverse, but leather and suede are prevalent, which only makes them quality items. If you had any questions about ankle boots, we hope we managed to answer them with our guide. Our comprehensive list includes boots we believe work good with everyone, and we do hope that you have found your new autumn pair!

Frequently Asked Questions

q: Is the style of my ankle boot important?
a:

Choosing the right style of ankle boots does seem like a troubling task, but believe us, it’s not. You should choose the style depending on the occasion you will be attending (casual, formal, or something in between). For casual events, Chelsea and Chukka boots work great! They are simple in design and complement plenty of various clothing combinations. Timberland boots are a great casual option too, working even with sweatpants. Chukka and Chelsea boots can also be smart casual or even business attire. For formal events, you can go with Oxford boots or any of the boots we listed in our guide with formal details added on!

q: How do I wear ankle boots?
a:

The length of ankle boots is what gives them their name, and their versatile look. But, to some people, this length is confusing. Do you tuck them in your pants, or do you let the pants hide them? Are socks important? For Chelsea boots, you can do whatever you like. Both tucked in and not look great since most of their appeal is in the front. For the other types though, wear pants that just reach your ankles, leaving the bootie completely visible - or you can cuff your pants, which can also add an interesting detail. Socks should be thin, and match either your pants or your boots - but if you’re feeling frisky (and you’re not going to formal occasions) you can explore different colors and patterns!

q: Do ankle boots need to have heels?
a:

Well, no shoe has to have a heel, but trust us you do want them! Contrary to popular belief, completely flat footwear can cause health issues too. Arch pain is the most common one since you will have nothing there to support them. Sole pain can happen too, and you can feel overall foot aches. So always try to buy a pair that has a little short heel (or proper midsoles) and you can avoid this issue completely.

q: Can ankle boots be formal?
a:

Of course, they can! Besides, what else would you wear to formal events in the autumn or winter? You can go in regular dress shoes, but you’d probably freeze. Just look for polished pairs and formal details, like wingtips or brogues. Leather that has a lovely finish can work with the most extravagant of outfits, and will bring out your inner shine!

q: Does the brand of my ankle boots matter?
a:

It does, but not in the way you might think! Sometimes, a popular brand can be pricey but really not that good, so you’d be paying only for the brand name. Check out the brand before you buy their shoes; are the reviews good? If not, skip it entirely. Find a brand that combines style and comfort, since these are the two things you should look out for the most. You might even end up paying less if it’s a local company or a smaller brand!

Sources

  1. Dr. Steve Rosenberg, How to Make Fall Boots and Booties Comfortable, Medical,
  2. Multi, Chelsea boot, Encyclopedia,
  3. en.wikipedia.org, Chukka Boot, Encyclopedia,