How To Buy A Men’s Boot

How to buy boots

Look how the outsole attached with the upper,❞ says Simon Crompton

Do you enjoy wearing a boot? Well, such indulgence depends on your relationship with boots, and that relationship depends on the boots you wear. We want you to think of ❝where boots stand in your life’s priorities.❞

The caliber of boots you own, their initial outlay, how often you wear ’em, and how nicely they serve the purpose you need them for—it, in conjunction, defines How you think about boots and How easily you spend on ’em.  

We’re explaining all this to you, Mr. Lavish Spender, because you approached boot purchases thoughtfully, researching How To Buy a Good Boot before you actually buy one. The idea of this guide is to encourage readers, like you, to buy boots in a more mindful way. 

In all honesty, getting a pair of boots is as complex—or as simple—as you choose to make it. Fortunately, the pace, of this guide, is more relaxed. There’s no right or wrong approach. The best writers have written our learnings into a guide you can happily absorb.

For What Do You Need A Boot?

Over a Century, Boot has made many attractive cases for itself

What are you supposed to do in your shoes? In a decade, designers have pushed many footwear styles beyond their original purposes, with no dramatic redesigns, that it is hard to keep your—for instance, White Sneakers or leather Oxford shoes—unused! 

Boots, being a footwear style for around 1,800 years, have evolved more illustrations ❝of their desirability❞ than any other style. We tend to believe that all boots are evaluated on a universal scale of versatility, but in fact, each occasion has its own boot.

It’s always interesting to learn why people choose the boots they do, and we learned about some purposes that were new to us, too. However, boots, for many, are still tough footwears, which seems to make sense because being robust is a boot’s most immediately striking need. 

But the essence of guarding our feet through footwear is more diverse today from, well, when we first wrap our feet with leather mimicking a boot. A work boot is protective, but it doesn’t necessarily suggest the protection the way hiking boots might. 

It’s a dress boot, that we always prefer to pair with the smartest tailoring in our studio or a meeting, but our lazy-style-oriented mind always saves a thought for The Great Laceless Chelsea boots. 

Lace into a pair of hulking construction yard shitkickers below your best soft-shouldered double-breasted suit: and that odd extra attention will help you put some faith in our belief that The needs of the moment dictate the sorts of boot we choose, and how those boots meet and contribute to your outfit and the moment is a measure of greatness.

Understanding the purpose of the boots and their meaning to you is crucial to zoom in on the sort of pairs that’ll serve you best. But when the desire to own Boots is not driven by a reason—that, surprisingly, is the most mature reason to buy boots. 

If you are one of the above, then it is more likely that you’ll find a boot that’s more interesting, more complex, and defines your taste, personality, and (not to be crass about it) status in this cupidinous world of ours – well, here are some classic styles of the boot to give a little context.

types of boots

How Much You’d Spend On Boots?

Try to be generous, please!

How much spend on boots

You might have roughly outlined What you want those boots to do. But, How much are you willing to pay for what they’d do? Even if your only concern is your wallet, pursuing a price barely makes your quest for boots better. But clarifying it, though, does make it seem more logical.  

Despite no direct correlation between the price of a pair and the quality of the boots, setting the financial boundaries is a crucial determination that can only be made individually, depending more on where boots figures in your life’s priorities than, well, on your bank account.

By dictating your cut for boots, you’re actually subscribing to a specific echelon of boots and eventually reeling in those oh-so-tempting shopping sprees. 

Higher prices do not guarantee better boots, but if you want to explore the world of fine boots, to really get to know it, you have to be willing to spend some money. 

For my money, though, we try to avoid excessively costly boots and to seek value in my closet and suggestions. Having written over boots for years, we get to know that the best values in boots are between ₹10k and ₹15k. 

Good boots in that range cost enough (barely) to finance conscientious bootmaking and quality materials. Once you get below that, compromises are inevitable. We believe there is no point in buying boots unless you’ll enjoy wearing them. 

This is not a universally held opinion, but if what you are after is mere synthetic leather footwear, there are better ways to achieve it than wearing the cheapest available plonk.

It would be easy to justify ₹15k for a Welted boot if you understand that quality leather and manufacturing come at a premium or have ever experienced a quality boot’s crazy ability to stimulate emotions. 

And if that amount seems too far from the number you’ve placed… don’t stretch! Adding a few hundred rupees to choose and wear better boots could develop a desire for ever-better boots and the initial outlay would gradually feel reasonable. 

What Makes Great Boots… Great?

Learn How To Read A Boot’s Quality

It would be foolish (and a little gauche) to place a boot on the ladder of greatness just because it broke your credit card. Cost never automatically equates to quality but takes you to some specific shelves testing your abilities to find boots that represent good value for the money you’ve decided to pay. 

Then, Who is to say what a “Good Boot” is? Is it one that has chunky rubber soles? One that is placed vertically on supermarket shelves? One that costs more than ₹20K? There is, of course, no definition. 

As older we get writing about shoes – the further along my footwear journey – the more we realize how subjective narrating greatness in boots can be. Many associate greatness with boots that showed toughness and presence. ❝A working man’s tool,❞ and sold. 

Some couldn’t restrain their boots to just heavy duties, and the best boots, for them, should be elegant enough for, well, every duty. It can quickly become philosophical, but the greatness of a boot is classically described on the authority of craft. 

In the 1,800 years of legacy, boots evolved and refined a form for every state and occasion. And, unlike other footwear styles, fine-tuning boots into many categories feels so natural and original that even a little more refinement will drop the integrity. 

How nicely the construction and material of a boot align with your Boot-ing purposes would actually define the rather subjective greatness of Boots. So it helps to be honest with yourself about purpose, liking, and budget, and to know what makes a good boot.


The Hiking Boots

These are basically a tool (a.k.a gear) for High Kings: those who enjoy
heading up to harsh and brutal terrains.

How to buy hiking boots

What Is It?

Hiking boots are for the natural and purest environment, for which boots were primarily made, where they will serve their part of protection, support, and stability: rather than loafing in a soothing metropolitan setting.

Unlike hiking shoes, hiking boots are for ceding comfort to a hiker carrying backpacks over 15 Kilograms, varying from mid to high-cut, and often have a stiff shank incorporated between the midsole and outsole.

What Defines Quality in A Hiking Boot?

Boots are getting versatile, and so are the ways to get one. As more and more desire boots as their typical footwear, there are more doors, stores, webshops, and IG accounts where you can buy your next sole. 


The Work Boots

These are the kind of boots that’ll get the job done.

How to buy work boots

What Is It?

The essence of ❝Work‚❞ on the subject of work boots‚ doesn’t resemble a carpeted office, sitting at a desk, probably 9 to 5. Work Boots are for the kind of work that is physically demanding.

Each job has its own work boot. But unlike hiking boots, nailing which pair of Work boots to wear doesn’t call for extra effort. Your boots are informed by elements of your work or a style that feels right for your job.

What Defines Quality in A Work Boot?

Perfectly stands up to the rigors of hard physical labor: Work boots, originally, are commissioned by bootmakers of developed nations and were—more or less—perfected half a century ago.


The Derby Boots

A style, in particular, that sticks in the memory when
many conjure up a boot.

How to buy derby boots

What Is It?

Many recognize a derby boot by the construction of its facing tabs, for its country origins, or for its fitting qualities. To me, it’s a little bit formal tempered with a touch of off-duty, to create a silhouette that averages out somewhere in the middle.

Pretty similar to balmoral boots but with greater margins of adjustment―thanks to the open-lacing system―to ensure the right fit is achieved. But if we just scan the lacing system, every boot would qualify to be a derby boot. They are, in fact, defined by the materials and proportions.

What Defines Quality in A Derby Boot?

So what makes a great derby boot? It’s not as detail-y as the Balmoral boot, but the signs of quality in a derby boot are perceptible, and the process rarely changes.


The Balmoral Boots

The dressiest style of boot you can put yourself in.

How to buy balmoral boots

What Is It?

Have you heard the phrase ❝Suited & Booted?❞ In that phrase, the ❝Booted❞ one resonates deeply with the Balmoral Boots! What initially was created to walk the grounds of Balmoral―the Scottish estate of Prince Albert―today, many would prefer to describe Balmoral (the boot) as an Oxford in the form of a boot.

Favored by gentlemen for clinical settings, the sleek lines and no-frills profile are enough to understand it being dressy. A distinctive seam that runs parallel to the ground―which earlier is a defining characteristic for such boots―is now a point where many bootmakers gradually switch the material.

What Defines Quality in A Balmoral Boot?

Wrangling through suits is a tough part. Organizing the tie and trousers will be a challenge while parceling out suit space for folds and more details requires advanced techniques in both logistics and psychology.


The Chukka Boots

Apart from the typical hardwearing abilities, there aren’t
a mood the Chukka doesn’t complement.

How to buy chukka boots

What Is It?

There is no firm evidence to support different theories about Chukka Boot’s history

But what unites all those theories is the seven-and-a-half minute Polo game played in our country and the word ‘chukkar’, which is used in the context of taking a leisurely stroll.  

Followed by the fact that the polo players preferred to stroll around in boots―similar to today’s chukka boots―after a game rather than in their polo boots. 

Not that a history lesson helps you actually figure out what it entails, but CONTEXT is important. This is, perhaps, why the Chukka boot is often an afterthought for many. 

Raised just to the ankle, enough to qualify to be a boot, with three open lacing eyelets, utmost, are enough for a boot to be called Chukka. Today, we can get a pair for every need. They come in canvas, suede, leather―in neutrals, and standout colors.

What Defines Quality in A Chukka Boot?

I know bootmakers in our country have spawned many excellent Chukka boots since the early days of my affection with ’em.


The Desert Boots

A style that shows how a boot can be worn, well, in the heat.
Perfect for those who are too erotic for sandals.

clarks desert boots

What Is It?

Many think of boots primarily as an accompaniment to colder weather, ‘coz you’ve either doubted a boot’s inner fortitude when it came to beating the heat or have never introduced your-shelf to desert boots.  

A type of Chukka boot designed for hot weather from the very start, the Desert boot represents the apex of summertime footwear versatility. Most recognizable by soft suede with a bouncy, crepe rubber sole.

Born in 1950, and inspired by the shoes worn by British soldiers fighting in World War II, its fascinating heritage could catch your attention more than design does.

Though, you don’t need to be near sand to appreciate this 60-year-old classic!

What Defines Quality in A Desert Boot?

A man’s choice of Chukka―from the many versions of a Chukka―initiates the mere act of reading its quality. However, we just have to navigate the quality, as what constitutes a desert boot is dictated from the day this style was born.


The Chelsea Boots

It’s the perfect hybrid that’ll immediately put you on
the smarter end of smart casual.

How to buy Chelsea boots

What Is It?

In context with the many reinventions of the classic Chelsea boot for the 21st century―a lot can be said to dictate what a Chelsea boot is. 

At their core, the best Chelsea boots for men are defined by two important details. First: a lace-less ankle-hitting height. Second: elastic gussets or elasticated sides with pull tabs.  

There is significant evidence to believe that the first Chelsea boot was designed by Queen Victoria’s bootmaker, Mr. J Sparkes-Hall in 1837. 

It was said that he created the pair of ankle-height boots with elastic inserts on either side, to make them easy to pull on and off for her majesty. 

Since then, it ceased to be a small part of London; Chelsea became international, and its name is interpreted as a way of living and a way of dressing far more than a geographical area.

What Defines Quality in A Chelsea Boot?

No boot style has been re-envisioned, redesigned, reworked, and iterated quite like a Chelsea boot. As every person has their own go-to version, pretty much every bookmaker has their own definition of this style.

How Boots Should Fit?

Bear in Mind―There are no industry standards
for what a size eight or nine should be.

How a boot should fit

The world, you see, is perhaps unsurprisingly full of these perfect boot wearers, and rather than a specific brand or site or store, the universal explanation came down to one idea: fit. 

Oh, come on, I’d say, you do know your size, right? That’s it! Who has the time? However, nobody’s normal. Sizes are standardized. Bodies aren’t. And, today, even those sizes weren’t all that efficient at fitting you a second skin anyway. 

For clothing, the idea of what the “perfect” fit looks and feel like is evolving as the film and fashion worlds embrace greater diversity. 

In shoes and boots, however, the subtleties of fit aren’t a matter of style and fashion. There are some timeless details to watch for when determining whether or not a boot actually fits you properly. But is it really…

Are Boots Suppose To Fit Like A Second Skin?

Many shoe enthusiasts and writers feel comfortable suggesting Second Skin is how the perfect shoe fitting should feel like. And that trait pursues the way many like to think about a Boot’s fit. 

I feel, in an age of increasingly mechanized shoemaking, many people, unfortunately, often grossly underestimate the cost of carving a boot to your unique specifications.  

Boots have the greatest fit potential. After all, what other style of footwear can a man wear that is so built up and rises over the ankle? 

It cost― roughly ₹100k―to commission a beautiful boot that hair precisely wraps a decent portion of your feet. But what if your Boots didn’t fit like that? Well, the impact depends on the type of boot.

Having written in-depth pieces on boots for years, I think many types of boots didn’t have to fit like a glove―especially those which tilt heavily over the functional side.  

Every type of boot has its definition of ❝The Perfect Fit❞ and its dimensions of deviation. The deviation between how a boot fits and the fit depicted by the sartorialist. 

Some room in hiking boots, for instance, is known to be a mark of perfect fit as it indulges your swollen feet during longer hikes. But a little room on leather derby or Chelsea boots can aggravate creasing―the most visible sign of low-quality leather. 

So just like the quality standards, there’s barely a fitting attribute that qualifies on every type of boot. Scroll to the genre of boot you are curious about, and the reading below will make sure you’re never wearing a poor-fitting boot. 

Size Do Help Begin 

Finding a boot that fits perfectly is not as complicated as selecting a size that perfectly reflects the proportions of your feet. 

Rightsizing your feet is actually the most mystifying and intimidating element of planning a boot’s fit. What ought to be a simple task often produces a feeling of dread and the fear of making mistakes―especially if you’re buying visually. 

That anxiety can set in for both occasional online shoe buyers and regular consumers. Counting on the type of store or online merchant you are buying a boot from… 

…you’ll get advice from more experienced people, except that advice is often uncomfortably specific, implying that only one size can do the trick, or mind-bogglingly complicated. 

You can’t recognize yourself from a list of measurements, but you can build up from there. Whether there’s an expert to assist, you’re buying online, or from a store where no one is happy to assist: begin with a pair of sizes you believe your feet belong to.   

That boot may not promise a perfect fit―though many times it does―but they help to ease the fears of making mistakes and act more like a base to compare and adjust from; until you feel the ideal fit.


The Work Boot

Work boots are typically heavier and more difficult to fit than conventional boots, which is understandable given the additional protection they provide to your feet.

The typical list-of-fitting attribute is confusing and somehow irritates. You just need to check three areas on your boot, which, pretty much, will cover everything it takes to get the fit right.

The Toe-box

As you work your feet swell and comfortable work boots have enough space for your feet to swell without causing discomfort. There should be plenty of space in the toe box to allow your toes to move a little.


The Hiking Boot

The typical process of trying on pair after pair until you find the best fit doesn’t work on Hiking boots if you don’t understand your needs; specific spots, for instance, where you demand support or stability from. 

In many manners, you can modify the fitting of hiking boots depending on the cut, degree of stretch, terrain, and the desired support. You should be really clear about how your new hiking boots should fit, even before trying one. 

Hiking boots have come a long way over the past couple of decades. It fitting has never been more inclusive, more flattering, more sustainable, and, well, more customizable. Here’s a break-down

The Toe-box

You want a boot that has enough room to wiggle your toes. If your toes have enough room to move around, they won’t rub against each other.


The Balmoral Boot

Well, it takes years, even for a master bootmaker, to define how a Balmoral boot should fit so it echoes the sophistication of an Oxford shoe. In fact, fitting possibilities of a Balmoral aren’t limited to just how good you feel in ’em. 

For a style of boot―which nurtures your finest tailorings―❝How the final fit LOOKS❞ is a fine detail that we might not think much about for any other boot. A boot may look awful, even if your foot sits perfectly into the boot. 

The Lacing Shape

Is ill-fitted Balmoral missing out on the beautiful I-shape that close-lacings Oxfords meant to have? The opening should be closed after lacing the Oxford, though many prefer a small V too.


The Derby & Chukka Boots

The only reason to buy a Derby boot (shoe) over a Balmoral boot (Oxford shoe) is the greater margins of adjustment that ensure the right fit from the very first time you try them on.

The fitting qualities come at the cost of sophistication and dressiness. On a primary level, a derby boot puts you in charge of your own micro-climate. 

It provides a decent fit and coverage, without any of the primness or frumpiness that so many contemporary iterations have drooped their way into. 

Overall, it’s the most online-buyable boot style. And maybe that’s why derby boots are badged with an extensive portfolio of brands you may have heard of. 

The Heel

Getting the heels right is, pretty much, the only thing about a derby fit that, if don’t fit perfectly, might push you to try a different pair.


The Chelsea Boot

How Chelsea Boot should fit

Is there any style of boots on which we place more expectations than our Chelseas? They need to look good. They need to feel comfortable. They need to go with everything else we own. 

And they need to last many years because we don’t want to go through the shopping process again any time soon. The aggressive marketing, leaning heavily on its laceless easy accessibility, made us believe in Chelsea…

…but not even whispers that Chelsea isn’t the most straightforward fit to get right. Well, it is the cost of firing the laces. It is a usual problem to which we’ve devoted a writing, that you might love to read if you’re drawn to many slip-on styles

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