Best Styles For A Versatile Shoe Collection

Fortunately, men’s shoes come in all sorts of designs, materials and colors. It’s a good thing that you have such a wide variety to choose from, but it can get a little confusing and overwhelming.

To start, you should at least get the basics covered as explained by my colleague Gavin in his article The 5 Shoes Every Man Should Have. Once you do that, why not branch out and mix things up to build a versatile shoe collection? Variety is the spice of life after all.

In this article I’m going to talk to you about 6 styles of shoes you should add to your rotation for some spice and versatility.

Ready to have some fun? Great! Let’s get started.

Chukka Boots

beckett simonon chukka boots

Mired in a murky history, the Chukka boot is something special. Some people think they were created for polo players to sport between periods of play called chukkas or chukkers, or after matches. The polo connection continues because the original Chukkas bore some similarities to the Jodhpur boots, which were in fact, created for polo.

Others believe British soldiers wore them while serving in the South African desert. Or did they originate in India for casual strolls called chukkars?

Whatever the real story is, the Chukka has been a wardrobe staple for almost a century, ever since the style made its way onto the feet of the general public. That public included the Duke of Windsor who - legend has it - was the first person to wear a pair on North American soil when he visited in 1924. Other aficionados of the style included Hollywood royalty Marlon Brando and Steve McQueen who seems to have had a real love for them.

In any case, the ankle-length, clean lines, thinner sole, open lacing system and two to three eyelets of the Chukka makes it a great choice for when you just want to kick around, or sport a casual look. The formality factor is influenced by the material the upper is fashioned from. For example, calfskin leather is dressier than suede or rugged pull-up leather which is shown above. The type of sole also changes the overall appearance with leather being more elegant as can be seen in our sleek Ellis Chukkas, whereas crepe or rubber signals informality displayed nicely with our Laval Chukkas.

Chukkas look cool with rolled-up cuffs, jeans, chinos, corduroy and shorts. You might even try them out with casual suits.


beckett simonon hoyt monkstraps

Did you know that Monkstraps started life in a very humble way? They were first created by monks as utilitarian footwear to help protect their feet while working long hours in the fields. Of course, the originals looked a bit different than the refined style you see today, but the basic idea remains the same. Convenience, comfort and practicality are still very much an important part of this design. 

Single Monkstraps, like our Leonards, used to be seen as the shoe you would wear only occasionally. Mostly worn by guys who stepped-out of the fashion norms, and flaunted their different point-of-view. To some extent that’s still the case. But, with the introduction of the Double Monkstrap, such as our Hoyts, the single suddenly took on a comparatively conservative air.

Monkstraps are amazing for a number of reasons. They’re always unexpected, add a surprising element to any outfit, look cool with or without socks, and go really well with anything from casual jeans to tailored suits.

In soft and supple calfskin leather or textural suede, Monkstraps are a “must have” for anyone who wants to mix-up their shoe rotation, and always be on point with their choice.

They are also incredibly convenient. Once you have the strap adjusted to the snugness you enjoy, you can leave it in place and simply slip your feet in and out with no trouble at all.


beckett simonon split toe derby

Just like other men’s shoe styles, the origin story of the Derby is like a fun mystery. As explored in my article The Difference Between Oxford and Derby Shoes, this now popular style was either constructed in the 19th century to be a gentlemen’s hunting shoe; inspired by a Prussian Field Marshal during the Napoleonic wars as an alternative to the stiff and clunky boots for his troops to wear; or commissioned by the 14th Earl of Derby who was in need of a comfortable shoe to support his girthful body.

The quarters are sewn on top of the vamp, which not only creates the defining open lacing system. It also provides more space for people who need a roomier instep.

Derbies are often considered to be a more casual dress shoe due to their open lacing system. That actually works to the Derby’s advantage since it can be worn comfortably with a wider range of outfits than more classically formal shoes like Oxfords.

Nowadays the Derby shoe runs the gamut from a formal look like a Clegg Split-Toe pictured above, to very casual, like our Dunham Derby in Pebbled Leather. 

A lot depends on the design, color and material they are made out of. Even though you probably wouldn’t pair Derbies with a tuxedo, they can still work well with nice chinos, twills, jeans and some suits. Derbies are the ultimate when it comes to dressing them up or down with ease.


beckett simonon beaumont horsebit loafers

You are most likely familiar with the Loafer, a shoe style that was first inspired by the moccasins worn by Native Americans. The design has changed a lot since then, of course. And, many variations can be seen all across the world.

Over the years since the original Loafer was introduced, it has become a true wardrobe staple. These are perhaps the most convenient shoes, and are what I like to call “street slippers.” Why? Because they are that comfortable.

Perhaps the most popular version is the Penny Loafer. But, the one I want to focus on is the Horsebit Loafer which was inspired by the equestrian lifestyle and tradition. Of all the versions of Loafers, the Horsebit, like our Beaumonts, is perhaps the one where you can still detect some of the hallmarks of the original inspiration.

Made with true moccasin construction, the insole is wrapped around the last so the upper becomes more flexible, comfortable and lighter than shoes where the insole is a separate piece of leather.

Every needle hole is punched, and every stitch on the apron is executed by the hand of a master craftsperson. The result is a loafer that feels like no other shoe you will ever own. The crown of this style is, of course, the solid brass snaffle laying across the vamp. What was once a humble instrument has been transformed into a symbol of elegance.

All of these details come together to create a shoe that is not only attractive, but highly practical. Wear the Horsebit Loafer with just about anything you’d like, including nice trousers, some shorts, casual or dressy jeans, or a suit. With or without socks, they will never let you down.


beckett simonon suede chelseas

Chelsea boots are amazing. Plain and simple - except they’re much more than that. This boot style actually ranks up there with the favorite styles of many people. Perhaps their most famous fans were the Fab Four themselves, The Beatles. But, they were actually created by Queen Victoria by the royal shoemaker J. Sparkes Hall. The queen desired something easy to put on and to take off for her country walks, and to go horseback riding with.

With the introduction of vulcanized rubber, the shoemaker had the perfect solution: create flexible, elastic side walls for normally constricting boots. This also eliminated the need for laces which the queen complained about getting caught in the stirrups.

Since they were created as riding boots, they were originally called Paddock boots. The name changed sometime between the 1950s and 1960s when the style was adopted by the rockers and mods who frequented Kings Road in the Borough of Chelsea, London.

A sleek, almost wholecut upper, and those snazzy elastic side gussets really make a statement. I mean, just look at these stunning Bolton Chesleas in Bordeaux as an example of how extraordinary Chelseas can be.

Wear them with tapered suits, slim fitting jeans or trousers or ankle-length pants and you will be swinging in the big leagues.

Balmoral Boots

beckett simonon balmoral boots

Also created for a royal, Balmoral boots are a style you might not know much about. This time it was Queen Victoria’s fastidious consort, Prince Albert, who tasked J. Sparkes Hall with creating a special type of boot for him; one that could be worn both outdoors and inside and always look good.

The shoemaker delivered a boot that was destined to become coveted by connoisseurs of fine footwear, and lovers of dress boots. The signature detailing of the Balmorals include thin lines of stitching which separate the lower part - called the golosh - with the form-fitting shaft. The golosh actually resembles an Oxford shoe, which is reinforced by the closed lacing system - as can be seen in our Elliot Balmorals pictured above.

Slightly unusual - or should I say uncommon - this style makes an instant statement, and will get people talking. They are perfect for the person who wants to make a statement without being loud or obnoxious.

Svelte and sexy, with a devil-may-care attitude, Balmoral Boots are well-suited for, well...suits. And cool trousers. And nice chinos.


There you have it, 6 amazing, and perhaps unexpected, shoe styles you need to add some versatility and pizzazz to your shoe rotation.

If you’d like to know how to best break-in your shoes and boots, check out this article. If you’re concerned about leather creasing, find out why you really don’t need to be, and what you can do about it by clicking here.

Let us know how you would wear any, and all, of the suggested styles by leaving a comment below.



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