Guide to Men’s Dress Shoes – What shoes should you wear?

Ever notice how an impeccable suit can still look a bit lackluster if paired with the wrong shoes? That’s because shoes, often underrated, play a starring role in the theatre of fashion. They’re the silent narrators of style, speaking volumes about a person’s attention to detail and personal taste.

On the practical side, they’re the workhorses, tirelessly supporting us throughout the day. But on the style front, they’re the final brushstroke on a canvas, tying the whole look together. A well-chosen pair can elevate even the simplest outfit, while a mismatch can overshadow even the finest attire. So let’s dive deep into the world of men’s dress shoes and ensure every step we take is a stylish one!

guide to men's dress shoes

The Anatomy of Men’s Dress Shoes

Stepping into the realm of men’s dress shoes can feel a tad overwhelming with all the jargon and choices out there. But, just like understanding the elements that make up a fine watch or car, grasping the anatomy of a dress shoe can truly deepen your appreciation for it. Let’s break it down piece by piece, unraveling the craftsmanship and design behind every step you take.

The Upper

First up, the upper. This is the top part of the shoe that wraps around your foot, made from materials ranging from leather to suede. It’s basically the face of your shoe, setting the tone for style and formality. Think of it as the suit jacket for your feet. The way it’s constructed and designed—like with broguing or without—can totally change its vibe.

The Sole

Then, there’s the sole. This isn’t just the part that meets the pavement; it’s the backbone of your shoe. While the upper shows off style, the sole is all about function. Whether it’s made of leather for that classic dress shoe feel or rubber for a bit more grip, the sole’s quality often dictates a shoe’s lifespan. And between the upper and the sole lies the midsole, providing that essential cushioning and support.

The Heel

The heel, that raised part at the back? It’s not just for height; it’s about posture and presence. A well-crafted heel ensures you walk upright and offers a rhythm to your stride. Some even come with a rubber insert for added durability, especially if you’re pounding the pavement regularly.

The Insole

Lastly, don’t overlook the insole. This is where comfort lives. It’s that inner part of the shoe that cradles your foot, often made from cushioned materials for added comfort. Because style matters, but so does feeling good in your shoes all day long. After all, what’s a dashing shoe if it feels like a foot trap?

Tying It All Together

So, there you have it – the intricate tapestry of design and function that is a man’s dress shoe. From the defining upper to the subtle comforts of the insole, every component comes together in a symphony of style and purpose. As with any fine art, understanding its composition only heightens our appreciation. The next time you slide your foot into that leather masterpiece, remember the craftsmanship beneath every step and stride with newfound respect.

Choosing a Shoe Color

Ever heard the saying, “Shoes make the man”? Well, while there’s more to a gentleman than his footwear, there’s no denying that the color of your dress shoes plays a pivotal role in your overall look. It’s like choosing the right shade of paint for a masterpiece. Each hue has its story, its occasion, and its statement. Dive in with us as we explore the classic, the versatile, and the daring colors that bring your outfit to life from the ground up.

Black: The Universal Pick

Black shoes are the unsung heroes of a man’s wardrobe. Much like the timeless black tie, they are your steadfast companions in the world of fashion — always dependable and eternally chic. Whether it’s the anxious moments before a job interview, the jubilation of a friend’s wedding, or just another day navigating corporate corridors, reaching for those black shoes is almost instinctual.

But why do we love them so much? Their versatility is unmatched. These shoes are the universal translators of the footwear world, effortlessly communicating elegance across a multitude of outfits. From the deep blues of a navy suit to the nuanced tones of gray, black shoes effortlessly bridge styles, ensuring you always step out with your best foot forward.

Exploring Shades of Brown

Ah, brown, the ever-adaptable relative in the shoe family. Where black shoes are like that reliable friend who’s always up for any plan, brown shoes are the adventurous ones, full of stories and character. The spectrum of brown is vast and varied, much like the myriad of experiences one encounters in life. Dive deep into its shades, and you find rich espressos reminiscent of cozy winter evenings, perfect allies for those heavier, formal fabrics like charcoal or deep navy.

But as the seasons change and the warmth sets in, brown effortlessly shifts gears. Its lighter tones, like the warm tans and caramels, beckon. These are the shades of sun-kissed beaches and lazy afternoon soirees. Not only do they find a harmonious match with summery suits, but they also lend a touch of refinement to casual ensembles, like a pair of well-fitted jeans. With brown shoes, it’s always about finding that sweet balance between elegance and ease.

Daring and Diverse: Other Colors to Consider

For the audacious gentlemen out there, craving a dash of flair in their step, the world of shoes offers a veritable treasure trove of options. It’s not just about the classic blacks and browns anymore. Enter the rich realm of oxblood and burgundy — shades that are imbued with an old-world charm yet feel incredibly modern. Their deep, wine-like hues make them unexpected standouts, particularly when paired with contrasting gray or navy suits. They have a way of lending an air of sophistication while making heads turn in appreciation.

And then there’s suede, the material that sings of luxury and tactile pleasure. Ever thought of sporting a blue suede or perhaps a mossy green? Perfect for those days when you want to break away from the norm or attend an event with a hint of whimsy. However, a word to the wise: when you opt for these statement shades, allow them to be the stars of your ensemble. Keep the rest of your attire understated and let those standout shoes bask in their well-deserved spotlight.

Tying It All Together

With all these color options, it’s tempting to amass a rainbow collection. But if you’re just starting out, focus on the basics. Secure a reliable black pair, dabble in a shade or two of brown, and then, as you become more confident, dive into the world of daring colors.

Remember, shoes are not just functional; they’re an expression of personal style. So, let your feet do the talking and make sure they’re saying exactly what you want them to!

Shoe ColorBest Occasions/When to Wear Them
BlackJob interviews, Weddings, Funerals, Formal events, Corporate meetings
Dark Brown (Espresso)Formal dinners, Winter events, Corporate meetings, With navy/charcoal suits
Light Brown (Tan, Caramel)Summer events, Casual outings, Beach weddings, With light suits or jeans
Oxblood/BurgundyFall events, Trendy parties, With gray or navy suits, Wine tastings
Blue SuedeCasual parties, Summer outings, Fashion-forward events
Green (Mossy, Olive)Whimsical events, Spring parties, Casual weekends, With neutral attire

Men’s Shoe Styles

Navigating the world of men’s footwear can sometimes feel like traversing a vast and intricate labyrinth. Each shoe style, from the artistic brogues to the casual buck oxfords and the statement-making wingtips, tells a unique story. These diverse designs reflect a rich tapestry of history, functionality, and fashion nuances, offering a perfect pair for every occasion. As you embark on this sartorial journey, understanding these distinct shoe styles can elevate your fashion game, ensuring that every step you take is both stylish and informed.


When one thinks of a classic shoe with a rich history and character, the brogue immediately comes to mind. These shoes aren’t just about utility; they’re a veritable canvas showcasing artistry and craftsmanship. The hallmark of a brogue is its decorative perforations – patterns made by meticulously punching holes into the leather. The variation in these patterns gives us the half brogue, where the design runs only midway, and the full brogue that sees this pattern dancing across the entire shoe.

Yet, it’s the medallion brogue that often captures the most attention. This design choice zeroes in on the toe, generously adorning it with detailed perforations, making it a focal point of the shoe. And while these designs might now be synonymous with style and class, they had a more practical origin. The brogue was born in Ireland, and its perforations were designed to let out water as wearers trudged through wet terrains and bogs. Today, they serve as a sartorial statement, enhancing business casual and semi-formal outfits with an air of timeless sophistication.

pair of brown brogues

Buck Oxfords

When you’re seeking to inject a hint of effortless style into your ensemble without going overboard, buck oxfords come to the rescue. Defined by their use of nubuck or suede, they stand out in a sea of traditional polished leather shoes. Their softer texture and matte finish lend a relaxed charm, making them the footwear of choice for less formal, more chilled-out occasions. Picture yourself stepping into a weekend brunch or strolling on a casual Friday in the office; these shoes effortlessly bridge the gap between casual comfort and dapper style.

But it’s not just about aesthetics with buck oxfords. While they might seem carefree, they come with a message. A message that whispers, “I’ve got an eye for fashion, but today, I’m in a laid-back mood.” So, while they might not be the star at a posh gala or a black-tie event, they play their role perfectly in settings where comfort meets style. In the universe of footwear, buck oxfords are that cool, easy-going friend who’s always up for a coffee chat or a leisurely walk in the park.

pair of buck oxfords

Cap-Toe Oxfords

Among the vast family of dress shoes, the cap-toe oxfords stand tall, proud, and undeniably classy. At first glance, what sets them apart is the distinguished ‘cap’ over the toe – a design feature achieved by adding an extra piece of leather. This touch not only adds visual interest but also a nod to traditional craftsmanship, making the shoe instantly recognizable and a favorite for those aiming for a polished look.

Yet, there’s more to the cap-toe oxford than meets the eye. While they ooze sophistication, they’re also the epitome of versatility. Tailored enough for a confident stride into the office, they’re equally at home at an upscale dinner or a night at the theater. However, if the invite says ‘ultra-formal,’ you might want to reserve them for less ceremonial outings. Nonetheless, cap-toe oxfords have a special knack for threading the line between formal charm and everyday elegance, making them a staple in every discerning gentleman’s wardrobe.

pair of cap toe oxfords


Dive into the world of men’s footwear, and you’re bound to stumble upon chukkas, a timeless classic often dubbed as desert boots. Their distinctive design features ankle-high construction combined with either suede or leather uppers, all tied together with open lacing and typically two or three eyelets. This combination brings forth a boot that’s both comfortable and stylish, radiating an aura of effortless elegance.

However, chukkas aren’t just about aesthetics. They also tell a story of versatility, fitting seamlessly into both casual and semi-formal ensembles. Planning to don them for work? It’s wise to first get a read on your office’s dress code. While chukkas might shine in a business casual setting, evoking a sense of relaxed confidence, a traditional corporate or strictly formal event might require something a tad more conventional. Still, for those who appreciate a blend of comfort with understated style, chukkas are a wardrobe essential.


Monk Straps

When you’re looking to add a dash of European flair to your ensemble, monk straps are your go-to choice. Evoking a sense of old-world charm combined with modern sophistication, these shoes distinguish themselves from the crowd with their unique buckle straps, forgoing traditional laces. Those preferring a cleaner, more streamlined look often gravitate towards the single strap variant, which, besides its aesthetics, can offer enhanced comfort for some. On the other hand, the double strap style is all about making a bold fashion statement, drawing attention to the foot with its distinct design.

But monk straps are not just about their captivating appearance; they also speak volumes about a person’s fashion sensibility. Perfectly suited for office wear and casual soirees, they seamlessly blend form and function. However, for ultra-formal galas or black-tie events, it might be wise to opt for something more traditional. When you step out in monk straps, remember they’re meant to shine — pair them with a more subdued outfit and let these shoes do the talking.

monk straps

Penny Loafers

A symbol of relaxed elegance, penny loafers have long captured the hearts of shoe aficionados. With their iconic slit at the instep, a nod to a bygone era where one might stash a penny “just in case,” these shoes speak of tradition while adapting to contemporary tastes. Comfortable, slip-on, and devoid of the fuss of laces, penny loafers are a testament to the notion that simplicity often yields the most timeless style.

While they effortlessly complement casual outfits, especially when paired with chinos or jeans, penny loafers are also daring enough to venture into the business-casual realm. When worn with a well-tailored suit, they bring a hint of nonchalance to an otherwise formal ensemble. However, while they’ve broadened their horizons, the grand ballrooms of ultra-formal events might still remain foreign territory for these classic shoes. Always remember, with penny loafers, you’re not just wearing shoes; you’re donning a piece of history.

penny loafers

Plain Loafers

There’s an understated elegance to plain loafers. Devoid of embellishments and flashy designs, these shoes let their simplicity do the talking. They are the embodiment of the phrase, “less is more.” In a world filled with complex designs and patterns, plain loafers stand out by blending in. The absence of defining attributes gives them a chameleon-like ability, making them suitable for a myriad of outfits and occasions.

What truly determines their versatility, though, is the quality and finish of the leather. A glossy, high-shine finish might elevate its stature, making it apt for business settings or semi-formal events. On the other hand, a matte finish or soft leather can render it perfect for a relaxed afternoon or a casual night out. Regardless of the variant, plain loafers are the unsung heroes, offering sophistication without the shout.

plain loafers

Side Gussets

Imagine a shoe that hugs your feet just right, every single time. That’s the charm of side gusset shoes. Recognized by their elastic sides, they effortlessly mold to the contours of your feet, ensuring not just a perfect fit, but unparalleled comfort too. The absence of laces or straps gives them a clean, uninterrupted design, which only accentuates their elegance. They’re a testament to the idea that simplicity, when done right, is unparalleled in its appeal.

But don’t be fooled by their simplicity; these shoes pack a punch when it comes to versatility. From boardrooms to bars, they seamlessly adapt, proving to be a worthy companion. Their design makes them an obvious choice for those who prioritize comfort without compromising on style. So, whether you’re stepping into a crucial business presentation or stepping out for a leisurely evening, side gusset shoes ensure you’re always putting your best foot forward.

Split-toe Oxfords

There’s a certain boldness to split-toe oxfords that sets them apart. The defining feature, a prominent stitching line bisecting the toe, not only adds character but also an element of artisanal craftsmanship to the shoe. This design isn’t just about aesthetics; it’s a nod to traditional shoe-making where every detail was crafted with purpose. The slightly bulkier structure ensures they stand out, lending weight and gravitas to your step.

In the realm of office footwear, they’re the audacious heroes, making their presence felt, especially when paired with a sharp suit. But it’s not just about show; it’s about making a statement. When you slide into split-toe oxfords, you’re choosing a shoe that speaks of confidence, attention to detail, and an appreciation for classic, timeless design. Whether it’s for a big meeting or just another day at the office, these shoes ensure your style quotient is always a notch above.

Tassel Loafers

Ah, tassel loafers, the delightful blend of tradition and playful elegance. Characterized by their dangling tassels, these shoes harken back to an era where style was all about flair and flamboyance. Once the darling of the sophisticated crowd, these loafers carried with them a sense of whimsy in an otherwise formal world. They were the showstoppers, the conversation starters, and a mark of the style-conscious gent.

Fast forward to today, and while their ubiquity might have waned, their allure hasn’t. The modern man who sports tassel loafers is making a statement – he appreciates the classics but isn’t afraid to infuse a touch of quirkiness into his ensemble. They’re the go-to choice for someone who wishes to add a vintage vibe to their outfit, be it at a throwback party or even just a regular day at the office where one wants to channel some old-world charm.

tassel loafers

Wing Tips

Wing tips are a staple in many a discerning gentleman’s wardrobe. At first glance, what truly captures the eye is the intricate brogue detailing, artfully splayed out on the shoe’s toe, reminiscent of wings in flight. This design not only adds character to the shoe but also brings a touch of panache to the wearer’s ensemble. Whether it’s to enhance your daily business attire or to add a sophisticated touch to a casual brunch outfit, wingtips are your trusty companions.

However, as versatile as they are, even wingtips have their limits. While they shine in many a setting, when it comes to ultra-formal black-tie events, it might be wise to opt for something a tad more understated. It’s all about understanding the occasion and letting your wingtips elevate your style where they shine brightest.

Take a look at the table below to see when you’d want to wear each different style of shoe.

Shoe TypeKey AttributesBest Suited For
BroguesPunched hole patternsBusiness casual, Semi-formal events
Buck OxfordsMade of nubuck/suedeCasual Fridays, Relaxed outings
Cap-Toe OxfordsDistinct toe ‘cap’Office wear, Dinner dates
ChukkasAnkle-high, 2-3 eyeletsFormal and informal settings (depends on office)
Monk StrapsSingle/double strapOffice, Casual outings, Not for ultra-formal
Penny LoafersSlip-on, slit at instepCasual outings, Business-casual office settings
Plain LoafersSlip-on, sleek designBusiness meetings to casual outings
Side GussetElastic sidesBusiness to casual occasions
Split-Toe OxfordsStitching at the centerOffice wear under tailored suits
Tassel LoafersDecorative tasselsRetro-themed parties, Office with flair
WingtipsBrogue wing patternBusiness wear, Casual outings, Not for black-tie

Making Your First Dress Shoe Purchase

One thought to keep in mind when buying a pair of men’s dress shoes is that the less ornate the shoe, the more formal it is.  This might seem counterintuitive, but it’s true.

While a nice pair of wing tips or brogues might require more work to produce than a pair of plain oxfords, it is less formal.  The reason for this is that the shoes with the least amount of styling will stand out the least.  This allows the suit, as well as the man in the suit, to stand out on his own.

Robert Phillips

From classic styles to the latest trends, I take pride in empowering my visitors with knowledge that enhances their personal style and boosts their confidence. As an advocate for the art of dressing sharp, I'm committed to inspiring men to exude sophistication and charm in every step they take, one perfectly fitted suit at a time.

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