While priming your wardrobe for your suiting, shirt and casual wear staples is absolutely imperative, no set of attire is complete without the perfect shoes. In this detailed guide on essential shoes for men, we will cover both formal and smart casual shoes that every aspiring dapper gentleman should own.

The stage is set. You’ve adorned yourself with that perfect attire for the occasion. Flat front pants, an impeccably tailored shirt and a bespoke suit that fits like a glove. Like your body was poured into it, filling it seamlessly as it shaped its way around your body lines, muscular definition and bone structure, forming that perfect silhouette.

Yes, that’s right. You’ve worked damn hard for the perfect suit, and you’re ready to make an impression on the day – whether its for an important presentation of your own wedding! However, that elusive question that always seems within sight, but never fully resolved, lingers in the background. What pair of shoes do I wear with this damn suit? What color and style of shoes would complement my ensemble, so that I can literally (no pun intended), put my best foot forward.

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Transplant yourself to another setting. You’re read to strut those slim fitted dark jeans or chinos, along with the perfect dress shirt to go with, or in the summer months, that effervescent Henley that makes you look dapper chic. Effortlessly sartorial. You’re ready for that big date night, and the conundrum rears its ugly head again. What shoes do I rock with this ensemble that’s going to bring in an aesthetic level of consistency, while allowing me to portray my values through the manifestation of clothing. 

In this detailed guide regarding essential shoes for men, we will cover both formal and semi formal / casual shoe options for men, so that you are always dressed in congruence with both your intention and the setting that you are attending.

Types Of Formal Shoes

Before delving into both formal and informal shoes on the essential shoes spectrum, we thought it would be helpful to discuss the anatomy of a dress shoe. From back to front, a dress shoe is comprised of four key components – the toe, the vamp, the facing and the quarter.

It is the construction and attention to detail with respect to these four components that largely determines the uniqueness of each shoe. As an example (which we will see in more detail below), Derby’s are often confused with Oxford Dress Shoes, even though a Derby Shoe features an open lacing system whereas an Oxford Dress Shoe comprises of a closed lace interface.

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1. Oxford Cap-Toe Dress Shoes

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The Oxford dress shoe, considered a staple in the dapper gentleman’s wardrobe, epitomizes luxury and tasteful selection. Oxford dress shoes started gaining popularity in the 1800’s with students at Oxford University.

Oxford dress shoes are characterized by their closed lace system, indicating that the shoes facing is secured beneath the vamp, leading to a more streamlined, sleek silhouette that is congruent with more formal fashion or events.

The Oxford Cap-Toe, on the more formal end of the oxford dress shoe spectrum (less formal than the oxford wholecut, discussed below), should be a staple in every discerning gentleman’s wardrobe. Characterized by an extra piece of leather across the toe box of the shoe, the oxford cap toe is ideal for more formal settings, and can be worn to an important presentation, cocktail party or your next wedding reception.

Courtesy of www.hespokestyle.com

The Oxford Cap-Toe can be strutted with a charcoal grey, traditional black or navy suit. This shoe is as formal as any gentleman needs on a regular basis, while also being versatile enough to be dressed down slightly for daily office wear.

The Oxford Cap-Toe will prove to be highly versatile as you wear it across a range of functions and settings. It is important to note that a higher quality oxford dress shoe is constructed of box-calf leather, in addition to not having any brogueing or perforations (which, as the name suggests, is typically associated with brogued shoes, which we will discuss below).

2. The Derby Shoe

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Often confused with oxford dress shoes, as mentioned above, the derby shoe was a sporting and hunting boot that came into prominence during the 1850’s. It was at the turn of the 20^th century that these shoes became commonplace as a fashion statement piece!

Derby Shoes, distinguished by their open lace system, are considered a more ‘casual’ dress shoe option. Courtesy of www.untamedstreet.com

Derby shoes are distinguished by their open lace system, with the facing attached to the top of the vamp, which leads to a looser, more casual fit that isn’t as streamlined as that of the oxford shoe. Consequently, these shoes are considered more versatile and can be worn to a range of settings, whether it’s a summer wedding with a linen or cotton suit, or with a pair of well fitted dark denim jeans!

3. Wingtip Brogues

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Wingtip Brogues are considered less formal shoes that can be worn with a range of suits, including lighter grey, blue, navy and brown suits. These shoes are considered essential, as they can be used to dress down slightly more formal attire, or dress up a more casual getup.

Brogue shoes, which feature perforated holes, originated in the marsh conditions of Scotland, where workers would often wear them to help the shoes drain out excess moisture. It is important to note that any style of dress shoe can feature broguing, as it refers to the decorative perforations in various patterns. Broguing can therefore be seen across a range of shoe styles from oxford, derby and monk strap, across four cap toe styles: full brogue, wing top brogues, semi-brogue and quarter brogue.

 Wingtip brogues, where the lacing is secured beneath the vamp, are more formal in nature (brogued oxfords, essentially), and can therefore be worn with a suit. Courtesy of www.pinterest.com

Brogue dress shoes will quickly become the perfect wardrobe complement, as they can be worn with virtually any suit color and due to their durability, be worn to the office day in and day out. Whether you are dressing up for daily work, or an important business meeting, these shoes will make you seamlessly fit in at practically any setting.

While brogues are generally available in a variety of shades of brown, darker shades will lend themselves to more formal settings, whereas a lighter shade of brown will be best used within a less formal capacity.

The Dark Knot Tip: The trick, with brogues is – to figure out which brogues are most appropriate for formal vs informal settings. While color, as mentioned above, will play a critical role in your decision making process, ascertaining whether the brogued shoes you are evaluating are open laced (derby) or closed lace (oxfords) is of paramount importance. Open laced brogues will not look appropriate at an important presentation or a more formal office setting, whereas closed laced brogues that feature perforations on an oxford style shoe, will be more apropos for a formal office setting or important business presentation.

Brogues with lacing above the vamp (derby shoes) are considered more casual and can hence be worn with denim or chinos on an evening out! Courtesy of www.pinterest.com

 4. Double Monk Straps

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The double monk strap, as its name suggests, originated with monks that used to wear them as a more protective option to their traditional sandals. Monk strap shoes emerged as a fashion trend in England in the 1900’s and have remained a mainstay with men’s style ever since.

While the single monk strap shoe is the original monk strap, the modern interpretation of the double monk strap makes it an ideal addition to our list of essential men’s shoes.

While the double monk strap resembles the shape and construction of an oxford, it features wider swatches of leather fastened across the front of the shoe with a double buckle. Though double monk strap shoes are typically available in a range of colors, the brown and oxblood variants, with good reason, are by far the most popular.

Double monk straps are highly versatile and can be worn across a range of settings. While darker double monk straps will work best with a charcoal grey or navy blue suit, a medium shade of brown monk straps could work exceptionally well with either a suit or a pair of well fitted jeans or chinos. For some European flair, try opting for a pair of rolled chinos!

Alternatively, if you are looking for a pair of more ‘casual dress shoes’ with a lighter colored grey or blue suit at your next summer wedding, or country club cocktail party, a pair of lighter or medium brown double monks will work exceptionally well.

5. Oxford Whole-Cuts

The Oxford Whole-Cut, the second oxford dress shoe to appear on this list, has become a gentlemen’s wardrobe staple in recent years. This dress shoe features a simple, elegant design constructed from a single piece of leather without a back seam. Given that a whole-cut is constructed from a single piece of leather, it is a truly unique shoe that also happens to be delicate.

Being constructed of a single piece of leather, it is imperative that the shoe goes through a rigorous manufacturing process. It is for this reason that Oxford Whole-Cuts are typically found at higher-end shoe retailers.

Oxford whole-cuts are extremely sleek shoes that are best suited for more formal occasions. Courtesy of www.paulevansny.com

Oxford Whole-Cuts feature a closed lace system, indicating that the shoelaces have been attached under the vamp. This, combined with one piece design, results in an extremely sleek and elegant shoes that is best reserved for more formal events or black tie settings.

Smart Casual / Casual Shoes

6. Loafers

Loafers are slip on shoes that typically feature a decorative segment. This could include a plain strap, a strap with a slit (penny loafer) or metal ornament (bit loafer).

With Norweigian roots, the first loafers came into existence in the 1930’s. Fisherman in Northern Europe strutted a slip on style of shoe similar to that of a moccasin, which quickly caught on, as men began to transition into every day smart casual wear when not wearing boots. It wasn’t until the 1960’s that American businessmen and lawyers started to regularly strut loafers with their daily office wear.

In 1966, Gucci revealed the bit loafer, which featured a metal strap across the instep of the shoe. Gucci’s revelation lifted the loafer shoe to another gear of formal wear, or at the very least, no longer precluded more formal settings as an option.

Bit loafers allow you to look casual, in a more formal capacity. Courtesy of www.asos.com

Penny loafers were developed years later, and are considered a more casual option that can be worn with chinos or slim fitted jeans, whether its for lunch or an evening out.

Penny loafers, as mentioned above, feature a strap with a slit opening. Penny loafers ease of wear and relaxed chic vibe make them the perfect option for dressing up while dressed down – creating a relaxed, elegant look without much effort! Now who wouldn’t want that?

Penny Loafers provide a great, casual shoe option. Courtesy of www.lanecrawford.com.hk

The Dark Knot Tip: If you are looking for a pair of shoes that can be worn with chinos or dark denim and still have you looking dapper and elegant, loafers are almost your defacto option. Easy and effortless (yes, that was needed for emphasis!), loafers are a no brainer when adding shoe staples to your wardrobe.  Penny loafers provide a more casual option, whereas bit loafers (with a metal ornament), are considered more formal and can be worn with a suit, along with tassel loafers.

7. Chelsea Boots

Chelsea Boots, alternatively known as Jodhur Boots, Paddock Boots or Dealer Boots, are ankle high, close fitting boots that feature an elastic side panel. This elastic side panel is a key component, allowing for ease of wear and being able to slip in and out.

The Chelsea Boot is the perfect representation of casual intersects with corporate. Falling somewhere between boots and dress shoes, they provide an incredible way to add contemporary flair to your style.

Suede Chelsea Boots provide for an incredible look! Courtesy of www.thursdayboots.com

Chelsea boots are available in a range of styles. Leather Chelsea boots are best suited for smarter settings, such as Friday night drinks, while suede Chelsea boots can work at all times of the day!

8. Chukka Boots

With a strong sporting and military history, Chukka boots have become incredibly popular, and hence, a non negotiable in every dapper gentleman’s wardrobe.

Chukka Boots are characterized as ankle high boots, typically made of calf skin, with an open lacing system and two or three pairs of eyelets.

Chukka Boots were conceptualized by a South African walking shoe design called the veldskoen (‘field shoes’), originally introduced during the 17^th century by Dutch settlers in South Africa. Given that these shoes were easy to manufacture, light weight and extremely durable, they quickly took over society and were worn by all classes and professions – often sans socks! The Chukka Boot was further popularized by the British Army during World War II, yielding this iconic boot the nickname ‘Desert Boot’.

While Chukka Boots are typically offered in a variety of styles, a definitive chukka boot must contain a few distinctive characteristics. These entail the top of the shoe hitting the ankle, two or three eyelets and a rounded toe box.

Additionally, Chukka Boots feature a noteworthy two part style (vs traditional one piece), a shoe with a folding over effect on the top of the boot where the laces converge. Chukka Boots are typically unlined and feature either a leather or a crepe sole.

Chukka Boots are best paired with dark denim or chinos. It is imperative that an appropriate color of trousers are chosen so as to avoid color clashes. For a more rugged look, through on a leather jacket, while a pea coat will add some level of formality to the look.

Chukka Boots provide a more casual alternative to Chelsea Boots! Courtesy of www.themodestman.com

The Dark Knot Style Tip: Aspiring sartorialists can often be confused when choosing between Chelsea Boots and Chukka Boots, and understandably so. There are a couple of key similarities between both. Both styles are ankle length boots, and both are designed primarily for the Fall & Winter Seasons. Both styles of shoes have been designed to provide your feet with added protection that you don’t get with traditional shoes or trainers. However, the key distinction is that Chelsea boots are best reserved for more formal settings, while Chukka Boots work best in a more casual setting. Both Chelsea & Chukka Boots can be worn with a smart casual ensemble!

Another way of looking at these two is that Chelsea boots are best seen as an alternative to more formal shoes such as Derby’s, while Chukka boots are seen as stand-in for more casual shoes such as brogues.

9. Boat Shoes

Boat shoes with their moccasin, loafer like style are the perfect shoes for summer months. Boat shoes are characterized by a rubber sole for superior grip, and provide the best water protection (go figure!). A key distinctive feature of boat shoes are the laces that run around the topside of the shoe. While these were initially in place for functional purposes, most contemporary boat shoes feature these laces from a purely decorative standpoint.