Casual shoes like sneakers are the backbone of men’s footwear fashion. They are comfortable, stylish, and highly versatile. But, no matter their quality or construction materials, they are not professional shoes to wear with suits. You cannot rock a pair of low-top sneakers to work with dress pants, button-ups, and a formal tie outfit as that role is reserved for dress shoes for men.
These shoes are an essential component of formal wear. To look professional, you need a pair of high-quality men’s dress shoes in your closet.
Best Comfortable Dress Shoes for Men
The world of dress shoes is vast with various types, color options, and material choices. Not to mention the extra knowledge like learning how to stretch leather shoes.
Navigating this world might seem daunting initially, but you can make it easy by looking at the best men’s dress shoes on the market. One factor that often intimidates us from even starting a conversation regarding dress shoes is the idea of them being uncomfortable – this is far from actuality. Dress shoes don’t necessarily have to be uncomfortable. It all comes down to their construction model and the quality of materials used.
At The Jacket Maker, you will find a great collection of comfortable dress shoes for men that ace in terms of style without compromising on comfort. Without further ado, here are 8 of the best dress shoes for men:
Greyson Brogues Oxford Oil Pull-up Brown Leather Shoes
If we had to recommend just one type of dress shoe, oxfords would be the one. They are timeless footwear that has been a staple of men’s dress fashion for decades and a good reason. They are the ideal starting point for your dress shoe journey and the prime example of leather dress shoes.
The defining feature of most oxfords is their closed lacing. In other words, the inner vamp edge is above the shoe’s facing. The result of this particular arrangement is a shoe that hugs the natural contour of your feet, giving it a very slim silhouette. The Greyson brogue Oxfords are the best dress shoes for walking – the Blake stitching has made these dress shoes for men incredibly lightweight and flexible.
The Greyson Brogues Oxford dress shoe for men is distinctive in its finishing style; oil pull-up – retaining the traditional heritage. Furthermore, its moccasin construction elevates the wing-tip toe design and hand-punched brogued detailing, making it an easy-to-style and classic pair in your shoe closet that is equal parts versatile and unique.
Greyson Brogues Oxford Black Nubuck Leather Shoes
The supremely comfortable men’s Oxford shoes are flexible and lightweight all thanks to their classic Blake stitching. The high-quality cowhide leather adds durability which further strengthens the water-repellent properties of the nubuck finish. The hand-sanded outsole is compressed with the heel and gains optimal traction via rubber capping.
As for styling these oxford dress shoes, pretty much anything goes. You can dress up with these shoes with suits and all that stuff, or dress down for a more casual-centric approach to dress clothing. Also, brown oxford shoes with brown pants are an excellent combo with nearly limitless possibilities.
Should you want to remove yourself from the traditional oxford shoes in black and brown, you can even get your order customized – order custom oxford shoes and get them personalized according to your requirements, and that too, at a reasonable price.
Dirk Brogues Derby Maroon Leather Shoes
Brogue shoes are extremely fancy and offer a glamorous and stylish look that is packaged with comfort and elegance. The closed-lace style is further elevated with rust-proof eyelets and seamlessly durably poly-cotton waxed laces. The color maroon is fantastically classy and stylish, enhanced by the brogue detailing.
The signature characteristics of brogue shoes are also their main appeal, and that is their decoration. You will find decorative stitches, serration, and perforations on the top in swirling patterns and connecting lines.
These can spice up almost any outfit you rock them under. Even the most professional-looking and serious suits will get a glow-up that’s stylish while following the formal fashion protocol. These are some of the best dress shoes for men under $1000 – you can find them in varied sizes or try out our custom-made shoes as well.
Dirk Brogues Derby Brown Nubuck Leather Shoes
Derby shoes look similar to oxfords, so much so that you might even confuse them with each other at first glance. The telltale sign of men’s derby shoes is their simpler design. They have a similar silhouette to oxfords but derby shoes are one of the best casual dress shoes for men.
Dirk Brogue Derby brown nubuck leather shoes are aesthetically gorgeous and one-of-a-kind. The interior is formed of naturally milled cowhide leather which grants the footwear its breathability and soft feel.
The construction is further enhanced with the use of the premium Blake stitch method – making the footwear supremely lightweight and comfortable. The Eva insole bedding cushions the foot and adds support and comfort to the wearer. The nubuck leather is fuzzy and formal, making these shoes your best option for a dressy outfit.
Attorney Derby Black Suede Leather Shoes
Derby shoes are less formal than Oxford; a great option as men’s casual shoes that can be used for dressing up. This casual nature is reflected in their material options as well. You can wear them with almost any oxford shoe outfit and they will work okay at worst. The Attorney Derby black suits are one of the most comfortable dress shoes on this list – all credited to their brilliant design and exquisite craftsmanship.
That said, since these high-quality men’s shoes are more casual-focused, wearing them with full suits is not a good idea. Instead, these work best below pants like chinos or rolled jeans topped with button-ups and polo t-shirts. A word from the fashion community – there’s no look more put together than black shoes with khakis, and even better, if those black shoes are in Derby style.
Its hand-sanded premium outsole gives a sleek and formal look that is further enhanced by the leather stacked heels with partial rubber capping. These black dress shoes for men are to die for – their water-repellent suede finish, closed-laced with wing-tip toe design, and leather stacked heels exude power, wealth, and confidence.
Boston Double Monk Strap Brown Leather Shoes
These are the middle ground between oxfords and derby shoes when it comes to being formal. This balanced design gives them the ability to work well on both sides. You can rock them with the most dapper suits or fancy cuffed jeans. The defining feature of these shoes is their lack of laces on top and a wide strap that then goes into one or two buckles.
When it comes to the lining of our wonderful Boston double monk strap leather shoes in black, its naturally milled cowhide leather interior is important to mention. The clean lining is soft, lightweight, breathable, and supremely comfortable. The Eva insole bedding cushions the feet and the outsole is constructed with premium and hand-sanded leather, giving you sleek and contemporary black dress shoes.
Boston Double Monk Strap Oil Pull-up Brown Leather Shoes
This dress shoe is unlike any other – traditional in terms of its look, this double monk strap has an interesting oil pull-up finish that pays homage to its classy heritage. The overall silhouette is slender and contoured. This fitted shape makes them some of the most comfortable dress shoes for men as well. The light brown tone feels like it’s following the famous latte trend.
The prime example of a stylish double monk strap outfit would feature a pair of dark blue jeans with rolled cuffs, a blue and white striped button-up, and a drab green blazer. You can also swap the button-up for a maroon turtleneck for more style, or swap the jeans with chinos for a more formal-inspired look. What you need to know is that these are superlative in terms of design and quality, and one of the most comfortable shoes for work.
Director Wholecut Black Leather Shoes
Wholecut is the sneakers of modern men’s dress shoes. Look formal enough to qualify for black tie tuxedo outfits in these men’s leather shoes made from full-grain cowhide leather. Styling wholecut dress shoes for men is both easy and complicated. Easy because they are exceptionally versatile.
You can rock the same leather wholecut leather shoe with a jeans & t-shirt combo and everyday office attire. But, this ease of styling is also the hard part. Since there are so many possibilities, it can be confusing to find the outfits that you like the most. Also, if you’re looking for the ultimate black shoes with khakis pants, these close-laced and Blake-stitched leather wholecut design is the way to go.
Now in case you’re wondering what shoes to wear with suits, you have a long list of options to choose from.
FAQ – Dress Shoes for Men
The wholecut leather shoe design is the best casual dress shoes for men. It is offered by The Jacket Maker has constructed these comfortable dress shoes so that men can clean up nice without having to put much effort – something they would gladly do. The clean-cut, close-laced, and wing-tip toe style is supreme at all levels of class and suave.
Blake stitching, despite being conventional, is strong and durable. This type of construction formulates some of the best men’s dress shoes. Its lightweightedness, flexibility, and durability allow these shoes to become comfortable office shoes for men. Thus, one can address that it’s comfort that is a top priority when giving a verdict of best men’s dress shoes.
Oftentimes we stress on the color best suited for dress shoes when one should ideally be focusing on its function and features. But it’s understandable since we look and get impressed by the color instantly. Hence, if one has to boil down the best color for men’s dress shoes, it has to be either black or brown – mainly because they’re classic but also because they offer versatility.
Yes, it’s okay to match the dress with shoes. However, if you’re confident and want to challenge norms, you can indulge in complimentary colors. For instance, you can wear a grey suit with the best comfortable dress shoes for men in brown or even black.
Usually, closed-laced dress shoes are deemed formal shoes because they have clean cuts and a sleek design. In addition, perforations and hand-punched brogue detailing are also usually found on wing-tip toe style footwear; also pretty formal.
Dress shoes are footwear that isn’t a sneaker or boots and pairs well with formal clothing. Any footwear that exposes your feet can’t be considered dress shoes either.
The minimum number of dress shoes a man should have is one. A man should own at least a single pair of nice dress shoes for formal events and situations. There is no upper limit, but the ideal would be to own at least one pair of each, oxfords, loafers, tuxedo shoes, and Chelsea shoes.
Dress shoes are the preferred footwear for formal clothing. They pair well with dress pants, button-ups, suits, and tuxedos.
The most versatile dress shoe color is the good ol’ black with brown following not far behind.
The most versatile dress shoes are loafers. The same pair can be worn under a tuxedo and a jeans/t-shirt outfit.
Dress shoes for men are essential. No matter your lifestyle or job, you need to own at least one pair of dress shoes for formal occasions. Sure, sneakers are great but you can’t wear them under a suit, or to a job interview. Different dress shoes also open a whole world of unique outfits and ensembles that won’t look good with casual footwear. The Jacket Maker has a wide collection of dress shoes, from leather loafers to men’s oxford shoes, you can get quality-assured footwear that is comfortable, versatile, and classy. You can even opt for custom dress shoes should you want to give a more personalized feel to your personal shoe collection.