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The Basic Men's Wardrobe Guide - Five Footwear Essentials

Men's wardrobe basic footwear

In modern day society, with an ever-expanding abundance of goods just a click away, choice is hard. The truisms of commerce that had stood for centuries - geographical barriers, limits on selection and even price - are slowly being eroded by the internet.

In many ways, this is fantastic. We can now shop the bazaars of Northern Africa and the markets of South Asia from the comfort of our living rooms, and get our purchases delivered with unbelievable speed. Whereas we were beholden to local shops and their prices, we can now seek out the best offers (did we mention that all our orders come with free returns, and that orders over £50 gets free UK delivery, by the way?).

However, there are downsides. When it comes to certain things, you can be faced with some many options that you become paralysed by indecision, and nowhere is this truer than with fashion. With everyone from huge multinational conglomerates to tiny local shoemakers now able to offer their wares to the masses via the web, and physical retailers scrambling to keep up as well, the choice has never been wider.

With all this in mind, itís perfectly understandable that most men simply donít know where to begin when it comes to building a succinct, reliable, versatile wardrobe that will stand the test of time and transcend the peaks and troughs of fashionable trends.

At Cloggs, weíve already put together a menís formal shoe guide, designed to offer those making their first forays into the veritable minefield of monkstraps and moc toes a helping hand, but thatís only one style of shoe. In this guide, weíll give you a rundown on what types of shoes that you should look to have in your wardrobe at all times, dos and do nots for each style, and when to wear them. Scroll down to get started, or click on one of the buttons below to jump to a specific style's section.

Men's formal shoes basics†††Men's casual boots basics†††Men's basic trainers†††Men's basic casual shoes†††Men's basic boots

Basic rules of thumb

Men's shoes basics

One of the key facets of this guide and the styles we discuss will be versatility - essentially, being able to mix and match shoes and clothes with ease. Obviously, it takes two to tango and your footwear will only be as versatile as your clothes. You can read a fantastic guide on how to create a basic, versatile wardrobe here.

In the same vein, if youíre someone who has a very certain sense of fashion and has built their wardrobe around that, then this guide can be adapted accordingly. The suggestions here have been made for people with no one single thread running through their wardrobe, if youíll excuse the pun.


When it comes to trying to buy genuine wardrobe staples, itís rarely a good idea to go for the lowest price point you can find. The old saying goes ďif it sounds too good to be true, it probably isĒ, and while this isnít always the case, itís general good practice to view footwear purchases as investments rather than ephemeral purchases. This isnít to say that every pair of shoes you buy should cost as much as the 200-year old Russian reindeer leather formal shoes we alluded in our menís formal guide, but just remember that, if taken care of, the right pair of shoes can last for years and will work out cheaper in the long run.

Niche styles

This guide is designed to cater to basic needs and those who want to be able to keep their everyday looks varied and fresh. Obviously, certain professions, holidays and pastimes require specialist footwear (such as hiking, in which case check out our hiking footwear guide).

Men's formal shoes basics

Whether you wear them day in, day out for your job or just for the odd special occasion, a good pair of formal shoes is an absolute must. For the uninitiated, navigating the sometimes labyrinthine world of formal shoes can be intimidating to say the least, so if you need some help on terminology or deciding which style and colour shoes will best suit your needs, why not consult our menís formal shoes guide?


When it comes to formal shoe material, leather is the definitive option. Suede brogues have come into vogue recently, although this tends to make shoes look less formal and therefore weíve included them in our casual shoes section below instead.

Leather comes in a variety of different finishes, and the general rule is the smoother it is, the more formal it is. Full and top grains are a great choice for formal shoes, with black patent leather being by far the most formal option. Elsewhere, embossed leather such as pebble grain can help add personality to the shoe, ideal if theyíre going to be see a lot of action as a smart-casual item.


As with the overall style of the formal shoe you opt for, the colour should be dictated by what social situation theyíre likely to be worn in, as well as what colour suits you tend to wear.

You can read more about all of this in our menís formal shoes guide, but as a quick rule of thumb:

Black - The most formal colour choice, black is also limited in its versatility. It works best with a black suit, but can be paired with dark greys and navys too, although it is restricted in its use in smart-casual ensembles.

Dark brown - Although not always working with black suits, dark brown tends to go with just about every other colour suit, and can be dressed down with chinos or jeans.

Tan - The least formal option, tan shoes look great when paired with more casual outfits and also work particularly well with lighter coloured suits.


The construction of formal shoes is entirely dependent on price points, and can play a decisive role in determining the lifespan of a pair. Cheaper formal shoes tend to be cemented, while brogues at a middling price point are often blake stitched, which offers some added durability and a slimline profile. Finally, Goodyear welting is frequently used on more expensive shoes. This complicated method of construction is not only extremely durable but also means that the shoes can resoled easily after their sole wears out. Goodyear welted shoes tend to be wider than ones which have been blake stitched.

Featured styles

Our featured formal styles cover a range of formalities and constructions. First is the Loake Chester, a tan Derby brogue that errs on the more casual side on the formality scale thanks to its colour, lace closure, wingtip toe cap and elaborate broguing. However, despite not being the most formal option, the Loakes are extremely high quality, with a double leather Goodyear welted construction.

Second is the Cheaney Lime, an Oxford that also boasts a Goodyear welt. Very much the formal choice of our three featured styles, the simple toe cap is the only aesthetic embellishment on the Lime. However, donít let this simplicity fool you - the Lime is a study in master craftsmanship.

Finally, the Ted Baker Martt is a versatile dark brown Derby brogue, complete with stylish burnishing on the toe and heel.

Dos and do nots

Buying to suit your needs goes without saying, but it's particularly important with formal shoes. Will you be wearing them for work? Do you frequently attend black tie events? A black cap toe Oxford may be the way to go. Will even your most formal ensembles be quite laid back? You can afford to experiment. Having more than one pair of formal shoes eradicates this need for selectivity somewhat and will enable you to rotate, which can do wonders for the lifespan of your formal shoes.

Perhaps more than any other style in this guide, formal shoes are the ones where the pricing rule we mentioned above is the most relevant. A good pair of formal shoes can truly last a lifetime, and will work out much cheaper than buying a pair every other year, so buying from a reputable brand such as Oliver Sweeney, Cheaney, Barker and Clarks shoes (as well as the brands we've featured) is always advisable.

Men's casual boots basics

One of the most versatile pieces of a manís wardrobe, the casual boot can be worn throughout the year. Less heavy duty than a pair of full boots but often tougher and more reliable than trainers or casual shoes, casual boots encompass a range of styles. Casual boots are often smarter than trainers, so they can function as a substitute for casual shoes or even formal shoes in certain scenarios.


While leather is still king, casual boots tend to have a bit more flexibility. One of our featured shoes, the Clarks Desert Boot, is famous for its use of lightweight suede, which stems back to the style's roots. If your main boots are built to last and can work with summer outfits, then you can afford to experiment with the style a bit more.


Once again, casual boots tend to be a lot more flexible when it comes to colour than regular boots or formal shoes. For versatility, earthy tones tend to be best, but given how interchangeable the style is with others on the list, you can be more adventurous with your casual boots. Blues and reds may not go with everything, but, done right, they look fantastic and bring a whole new element to an outfit.


With such a broad remit, casual boots come with a multitude of construction methods. As theyíre likely to be doing less miles than your regular boots, you can perhaps afford a slightly less sturdy design (especially if the casual boots you opt for are interchangeable with your casual shoes and trainers). The devil is in the detail, and it is often more than worth it to go for a slightly higher price point from both a comfort and durability standpoint.

Featured styles

Our first featured style is the Barbour Readhead chukka boot. Featuring a stacked sole and a beautiful oiled leather upper, the Readhead is a classic chukka boot that looks fantastic with jeans and can pass as a formal style if need be.

Second is one of most iconic footwear styles in the world, the Clarks Desert Boot. Similar to a chukka boot, the desert boot is differentiated by its crepe rubber sole and suede upper, chosen due to their lightweight properties, which made them ideal for walking on sand. Like the Readhead, the desert boot can function in casual to formal ensembles easily.

Finally is the Dr Martens take on another classic style, the Chelsea boot. Another incredibly versatile style, the Chelsea boot has been a perennial favourite for decades, and this Docs version is a fantastic choice thanks to its padded AirWair sole which offers comfort and durability in equal measure.

Dos and do nots

Casual boots can be highly versatile as well as extremely specialised. Based on what you're planning for your casual shoes and trainers, you can either go for a style that goes with everything like the ones we've featured , or something which works best with a certain aesthetic (although it's generally best to avoid buying footwear with only one specific look in mind).

Men's trainers basics

Street wear is a truly evergreen trend, and can be achieved in a variety of simple, minimalist ways. A classic combination of plain, block coloured t-shirt and jeans can be transformed into an on-trend look with the simple addition of a pair of the right trainers.


Given your trainers will see the most wear in summer, breathable canvas is a safe bet. Leather is also increasingly popular, and can lend even trainers an air of formality. As with every other style in this guide, which material works best for you will depend entirely on the direction the rest of your wardrobe leans.


Trainers are one of the few styles where you really can let your imagination run wild. Blacks and greys are once again the staples, but thereís no style where branching out can be more rewarding.

Take a look at your wardrobe and identify any dominant colours you may have, and then look for trainers either in complementary or contrasting tones to maximise the effect and make them stand out.


Like casual shoes, trainers are a broad enough category to resist any sort of ubiquity in terms of construction. Rubber cupsoles are a timeless feature to look out for if youíre searching for a more laid back, less athletic-looking trainer. The same is true for the amount of embellishments on the upper - the general rule is the more details, the more athletic the look.

Featured styles

Weíve gone for the old reliables with our selection of featured styles, with two from Converse and one from Vans.

The first choice is the classic low top Converse Ox in navy. Although clearly a casual style, the All Star has become so popular that it has even been incorporated into formal wear by some fashion-forward troubadours.

Monochrome trainers are definitely in at the moment, and these true white Vans Authentics tick all the boxes. Another evergreen style is leather trainers, and our final pick - the Converse Chuck Taylor All Star in black - marries the two fantastically well.

Dos and do nots

Be sure to keep your casual shoes and casual boots in mind when buying your trainers. Aim for at least one highly versatile style within the three, as choosing specialist options will limit your choices for casual summer wear.

Men's casual shoes basics

While casual shoes undoubtedly have a lot of crossover with trainers, for variationsí sake itís a good idea to have at least two pairs of laid back summer shoes. Depending on your style, you could trade the trainers for another pair of casual shoes, or vice versa.


Being predominantly worn in spring and summer, breathability is certainly a consideration when it comes to casual shoes, while water-resistance is less of one.

Being able to go barefoot and keep your shoes fresh are both important, so light materials such as suede, mesh and canvas are all great choices. When it come to leather, many summer styles such as boat shoes will offer special odour-blocking technology in anticipation of being worn in warm weather.


Casual shoes, just like trainers, give you the opportunity to break from the restrictions of formal shoes and really let your personality shine through. Light blues and vibrant reds are two classic summer colours, and you can go even further if you donít mind compromising on versatility somewhat with greens, purples and more.


As we mentioned in the materials section, breathability is paramount when it comes to casual shoes. The same is true of comfort, as youíre probably going to be doing more walking in the summer months than you are in the winter.

While high quality blake stitching or Goodyear welting are less important here than with other styles, itís still worth keeping an eye on the brand - big names such as TOMS have earned their reputations thanks to years of producing high quality goods that last.

Featured styles

Our first featured style - the Peter Werth Nesbitt brogue - is something of a crossover with formal shoes, although the Derby construction and suede upper means these are far better suited to a relaxed, smart-casual setting than most formal shoes.

Boat shoes - like these Timberland Classic 2-Eyes - are a tried and tested summer classic, and look just as at home with shorts as they do with chinos. The style began life as a yachting shoe, but has since become a staple prep style that is an absolute necessity for anyone whose wardrobe consists of more than their fair share of Oxford shirts.

TOMSí meteoric rise since being founded in 2006 has been largely on the back of their making a truly timeless style - the espadrille - available to an extent that it had never been before. Light, airy, and casual without looking scruffy, a pair of TOMS Classics espadrilles can tie an outfit together and give even the most casual of beach outfits a touch of sophistication without looking overdressed.

Dos and do nots

Not so much a tip for building your wardrobe as one for dressing well in general - just because these shoes are designed to be worn with casual outfits doesn't mean they can't still be smart. Once again, which style will suit you best depends on the rest of your wardrobe, but don't be afraid of straying on the more formal side of casual.

Men's boots basics

An integral part of any winter outfit, the bulk of a boot's silhouette naturally lends itself to the added layers of a winter ensemble. In contemporary fashion, itís also perfectly normal to see boots worn with jeans and t-shirts during summer, but with so many options for summer wear above, you might want to save them for more frequent rotation later in the year.


Leather is once again a reliable go-to, with suede also not unusual in boots. However, if winter wear is your primary goal for your boots, itís worth bearing in mind that suede is less water-resistant.

A durable rubber sole is a must, and a deep lug pattern is also desirable if the boots will see a lot of action outdoors.


When it comes to colour, itís best to follow the same rules of thumb as with formal shoes, particularly as your boots can often be tasked with replacing your dress shoes in winter (especially if you opt for brogue boots).

You canít go wrong with blacks and browns, although less popular colours, such as dark blues and reds, will effectively convey a sense of sartorial confidence, albeit while possibly trading off a little bit of versatility.


Perhaps more than with any other style of footwear in this guide, itís vital that boots feature a strong, heavy-duty construction, be it stitched or a modern technique such as injection molding. Repeated exposure to wet and cold will quickly separate the good quality boots from the lesser ones.

Blake stitched boots will tend to be a nice middle-point between waterproofing and price, but the gold standard is Goodyear welted boots.

A Goodyear welted construction is more common with boots than it is dress shoes, and for good reason - the additional water resistance provides is incredibly helpful in winter, and should your needs change, they can be easily resoled with a more appropriate outsole.

Featured styles

Our featured styles - the Cheaney Tweed C, the Dr Martens 1460 and the Red Wing 875 Work Boot - cover three of the key styles of boot to keep an eye out for.

The Cheaneys are a beautiful example of a brogue boot, offering many of the features youíd expect to see on a formal shoe transplanted into a taller silhouette and fitted with a rubber commando sole. Brogue boots are a great choice for those with wardrobes that err on the more formal side of things in general, looking excellent with cords or chinos as well as suits.

The Docs exhibit the punkier side of boots in general, with their rich history of being co-opted by various subcultures. Ideally paired with classic mod fashion - think shirts, jeans and pea coats.

Finally, the Red Wings are classic work boots - rugged, hardwearing and unashamedly masculine in appearance, with a sturdy moc toe rather than a smoothly curved toe box. These look fantastic with a whole host of outfits, particularly with Americana-influenced styling, such as check shirts.

Dos and do nots

Remember that your boots are likely to be your go-to - regardless of season - in bad weather, so choosing an option that will keep your feet dry and can withstand a bit of wind and rain is very important. A rubber sole with deep lugs will give you more grip in slippery conditions than a leather sole, which is also a big help.

We hope you find this guide helpful. If you're feeling generous and would like to leave us some feedback, use the comment box below - we read everything to make sure our guides are as up to date and as comprehensive as possible.

Images courtesy of Micheli Claudio Arredamenti and Style Park.

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