Are you in search of the best casual shoes for men that effortlessly combine style, comfort, and versatility? Look no further! In this article, we have curated a collection of must-have footwear options that are sure to elevate any outfit. From sleek oxford dress boots to timeless suede chukkas, we have the perfect pair to suit every occasion and personal style. Get ready to step up your shoe game and discover the ultimate essentials that every man should have in his wardrobe.


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Dress Shoes

When you’re getting ready for a date night, a wedding, or any formal occasion, a sleek and shiny pair of dress shoes is still the way to go. 


The most classic form of dress shoe—also known as a balmoral—Oxfords feature a vamp sewn on top of the eyelets, resulting in a sleek, formal look. 

Cap Toes

Cap toe shoes are capped with an extra layer of leather, adding an extra touch of visual interest and toe protection to your standard plain toe oxford. 


Brogues are heftier than the average dress shoe, with decorative holes originally meant to prevent water damage. They pair well with thicker wool trousers.

Oxford Dress Boots

Oxford dress boots are a symbol of a man who values quality craftsmanship. These boots offer warmth and coverage in colder months, with a breathable lining for summer comfort.

Oxford dress boots complement well-tailored suits or dress pants, adding a touch of class to any outfit. They can also be dressed down for a more casual look.

Oxford Sneakers

Oxford sneakers are a stylish choice for casual footwear. Pair them with jeans or chinos for a chic and comfortable look.

The oxford casual sneakers are comfortable and fashionable. Get a pair of brown or white oxford sneakers for all-day comfort.

Chelsea boots

What makes Chelsea boots stand out is their ease of comfort. These boots have elastic on the side for easy on and off, eliminating the need for laces.

Owning a pair of suede Chelsea boots in your closet prepares you for casual outings. Their leather build pairs well with jeans, trousers, and more.

Chukka boots

Chukka boots are the go-to choice for minimalist style. With just 2-3 lacing holes, rounded toes, and ankle height, they are versatile and fashionable.

Pair a light-colored chukka boot with your casual outfit for an elegant look.

Chukka boots have become more popular in recent years and are a wardrobe staple for stylish men.

Suede Boots

Suede boots add sophistication and style to any wardrobe. Made from soft, velvety suede leather, they offer luxury and comfort.

One of the most distinctive features of suede boots is their texture, providing a unique and luxurious look. The suede material is also comfortable and versatile, making suede boots a long-lasting choice.

The Chelsea Boot

Chelsea Boot Inspirationcredit: PinterestThe Chelsea boot is iconic in its design and offers versatility. It can be worn with jeans, chinos, or even suits.

Where To Buy Men’s Chelsea Boots

Mo’ Money No Problem

Chelsea ExpensiveFrye Chelsea Boot: Frye | Suede Chelsea Boot: Mr. Porter | The Dean Chelsea Boot: Paul Evans | Troy Chelsea Boot: Ace Marks

Ballin’ On A Budget

Chelsea BudgetDuke Chelsea Boot: Thursday Boots | Vianello Chelsea Boot: Aldo | Chuck Suede Chelsea Boot: Cestfini | Suede Chelsea Boots: ASOS Design | Jude Tonal Chelseas: TaftDid you know that the Chelsea boot has Victorian roots and has been around for over 150 years?

The Suede Chukka

Suede Chukka Inspirationcredit: PinterestSuede chukka boots are a versatile choice, landing above sneakers in formality. They offer tremendous versatility, pairing nicely with suits or dark wash denim and a white t-shirt.

Where To Buy Men’s Chukka Boots

Mo’ Money No Problem

Suede Chukkas ExpensiveSplit-Toe Suede Chukka Sneakers: Mr. P | Bowery Chukkas: Frye | Tod’s Suede Chukka Boots: Tod’s

Ballin’ On A Budget

Suede Chukkas BudgetFudge Suede Desert Boot: Clarks | Gordon Rush: Austin Chukka Boot | Bushacre 2 Chukka Boot: Clarks | Scout Chukka Boot: Thursday Boot Co.Chukka Boots The Complete Guide Everything You Need To Know Hero» Related: You might be interested in this Best Chukka Boots Complete Guide.


When you're facing tough situations, you need sturdy boots. These are the year-round boots that matter most. 

Hiking Boots

Hiking boots offer rugged appeal and rock-solid support. Modern versions use lightweight materials while providing weather protection.

Chukka Boots

Originally designed for British troops in desert locations, chukka boots have become a casual footwear icon. They are perfect for wearing with jeans or khakis.

Chelsea Boots

Invented in the 1830s, Chelsea boots are distinguished by their elastic side panels for easy slip-on wear. They cut a sleek and dressy figure, perfect for tailored pants.

Work Boots

Built for hard labor, work boots are tough and durable. They pair well with jeans and a rugged outerwear.

Dress Boots

Dress boots are taller versions of your favorite dress shoes, adding sophistication to your look.

Cowboy Boots

Cowboy boots are flashy, rugged, and elegant. They can be worn with bootcut jeans and Western shirts, as well as for subverting traditional suits or creating grunge-inspired outfits.


Sandals are a favorable choice for casual summer footwear. They complement casual outfits when styled well.

Sandals come in various designs and builds, from rubber to leather. They are perfect for hot summer days, allowing your feet to breathe.

Pair sandals with shorts, knickers, or casual trousers for a comfortable and stylish look. Avoid wearing socks with sandals.

Flip Flops

Flip flops are a classic choice for casual footwear. They are versatile, comfortable, and easy to clean.

Pair flip flops with shorts and a t-shirt for a laid-back look, or dress them up with chinos and a button-up shirt.

Flip flops offer breathability and arch support, making them ideal for hot summer days. They are low-maintenance and can be easily cleaned.

When choosing casual shoes, consider comfort, style, and quality to find a pair that suits your needs and lasts a long time.

Casual Loafers

Loafers are a must-have casual shoe for men. They provide comfort and showcase your sense of style during the summertime.

Loafers are smart and suitable for various outfits, whether formal or casual. A pair of brown loafers adds elegance to any ensemble, while navy loafers offer versatility.

Penny Loafers

Penny loafers are a versatile and stylish choice for casual shoes. They can be worn with shorts and a t-shirt or a tailored suit, making them a wardrobe staple.

Penny loafers exude confidence, style, and a touch of nostalgia. With their timeless design, they evoke images of carefree summer days and add sophistication to any look.


Moccasins are similar to loafers but with some key differences, such as their flat soles. These casual shoes offer versatility and can be worn with various outfits.

Moccasins have Native American origins and often feature decorative laces. They provide comfort and can be paired with casual outfits effortlessly.

The Monkstrap Shoe

Monkstrap Inspirationcredit: Pinterest

Technically, the monkstrap is considered a loafer because it lacks laces, allowing you to easily slip them on. There are options with a single strap, double strap, and even triple straps, with double straps being the most popular choice. People either love or hate monkstrap shoes. I see them as the grown man's version of velcro sneakers.

Where To Buy Men's Monkstrap Shoes

» Quick Note: You might be interested in this detailed comparison of Cole Haan vs Beckett Simonon.

Mo' Money No Problem

Monkstrap ExpensiveLeather & Suede Monk Straps: Mr. Porter | St. John's Double Monk Strap: Allen Edmonds | Brown Suede Double Monk Strap: SuitSupply

Ballin' On A Budget

Monkstrap BudgetWilliams Single Monk Strap: Cole Haan | Fletcher Double Monk Strap: Johnston & Murphy | Hoyt Monkstrap: Beckett Simonon

Did you know that the name "monkstrap" originated from an era in Europe when monks wore buckle shoes as an alternative to sandals?

Monkstrap shoes may not be everyone's cup of tea, but many stylish men have at least one pair of double monks in their wardrobe. They look best when paired with pants that have no break, allowing the shoe and buckles to take center stage.

The bottom line: Monkstrap shoes are incredibly stylish and can be worn formally with a suit or more casually with jeans and a blazer.

The Brown Leather Boot

Brown Leather Boot Inspirationcredit: Pinterest

Completing the list of essential stylish shoes for men is the brown leather boot. A pair of brown leather boots is a must-have for good reason.

Depending on the style, brown leather boots can add a touch of sartorial sophistication or ruggedness to your look. There are dress boots, casual work boots, chukkas, chelsea boots, and even cowboy boots.

Where To Buy Men's Leather Boots

» Quick Note: You might find this long-term review of Thursday Boots interesting.

Mo' Money No Problem

Brown Boots ExpensiveFirst Avenue Dress Boot: Allen Edmonds | Dalton Wingtip Dress Boot: Allen Edmonds | Heritage Moc-Toe Boot: Redwing | Evans 1000 Mile Boot: Wolverine | Iron Ranger 6" Boot: Red Wing | 6" Service Utility Boot: Chippewa

Ballin' On A Budget

Brown Boots BudgetCaptain Boot: Thursday | Lace Up Boot: Aldo | Full Grain Leather Wingtip Boot: Thursday | Rome Cap-Toe Boot: Taft | Dowler Cap Toe Boot: Beckett Simonon

Did you know that many heritage brand boots like Red Wing, Thorogood, and Wolverine have been around for well over a hundred years?

You can choose a more casual work boot or a stylish dress boot, depending on your preference. Whichever you go for, there is a certain charm in a well-worn pair of boots. Some guys even intentionally distress their boots for that desired worn-in look.

Allen Edmonds Dalton Boot Review 2022 (4 Years Later Still Worth It?)» You Might Like This: Allen Edmonds Wingtip Boot Review.

I recommend owning a brown pair of boots as they complement dark wash denim, corduroy, chinos, or wool trousers. Personally, I like to cuff my jeans for a casual flair when wearing rugged boots like the Wolverine 1000 Mile.

The bottom line: Brown leather lace-ups are both practical and stylish. They are the perfect option for fall and winter. Dress them up or dress them down, they will serve you well. Keep them clean and they'll last you a long time.

Quick note: If you're enjoying this article on must-have shoes for men, then you'll probably find my other writing on all things men's style useful. Each week, I share style tips, inspiration, deals, and more through my free email newsletter. To join now, just enter your email address below and click "Get Updates!"

The Brown Brogue

Brown Brogue Inspirationcredit: Pinterest

What is the first shoe every man should own? The brown brogue. It will quickly become a staple in any man's wardrobe. It's not only versatile but also stylish. Fun fact: the term "brogue" comes from "bro," the Gaelic word for shoe. Brogues are characterized by the unique decorative perforations along the leather uppers.

Where To Buy Brown Brogue Shoes

» Readers' Favorite: 10 Men's Dress Shoe Types: Oxfords, Not Brogues (Everything You Need to Know).

Mo' Money No Problem

Brown Brogues ExpensiveFifth Avenue Cap-Toe Oxfords: Allen Edmonds | Strand Cap-Toe Oxfords: Allen Edmonds | Grenson Leather Wingtips: Mr. Porter

Ballin' On A Budget

Brown Brogues BudgetLisbon Brogue Oxford: Ecco | Meliot Derby: Aldo | Larethienflex Oxford: Aldo | OriginalGrand Ultra Wingtip Oxford: Cole Haan

Did you know that brogues were originally designed to serve as drains for muddy water?

I recommend starting with a semi or quarter-brogue in a dark brown for your first pair. If you're feeling more sartorial, go for a full-brogue (wingtip) in a tan or cognac shade. However, if you prefer a more understated look, opt for a darker brown with minimal broguing. This will give you endless options for pairing with jeans, chinos, or wool trousers.

» Quick Note: You might like this comparison between Beckett Simonon vs Allen Edmonds.

The bottom line: The brown brogue is a cornerstone of the smart casual wardrobe. It can dress up well-fitting jeans or dress down a tailored suit. It's a versatile shoe that will serve you well from the office to the dance floor.

Casual Sneakers

A man's closet is not complete without a pair of sneakers. And this time around, we recommend owning a pair of stylish slip-on sneakers. These lace-less shoes have characteristics of loafers and are designed with comfort in mind.

Initially, sneakers were created for functionality and comfort, so slip-on sneakers are a natural evolution in that direction.

The beauty of slip-on sneakers is their ability to pair well with a variety of casual outfits. Invest in a pair of white slip-on sneakers with minimal design, and you'll find them worth it for most occasions.

Penny Loafers

But penny loafers are not just a nostalgic throwback. They are one of the best casual shoes for men who value comfort, style, and versatility.

You can wear penny loafers with anything from shorts and a t-shirt to a tailored suit, making them a true wardrobe staple suitable for any occasion. When it comes to casual shoes for men, penny loafers stand out for their confidence, style, and touch of nostalgia. They possess a timeless quality that sets them apart from other casual shoe options for men. Penny loafers evoke images of carefree summer days, sipping lemonade, and enjoying jazz music. Their clean, sleek lines and simple yet striking design also exude sophistication and elegance.

The Casual Sneaker

Running Sneakers Inspirationcredit: J.Crew

Last but not least, the classic casual running sneaker completes this list of essential shoes for men. Although they may not be used for actual running these days, they are perfect for casual outfits and the trendy athleisure look. Check out this Nike Internationalist Review to see how I styled this popular running shoe.

Whether you have errands to run or plans to meet up with friends, casual running sneakers offer the utmost comfort. Pair them with joggers and a ball cap or rolled-up jeans and a blazer.

A word on shoe odor - I highly recommend using this premium shoe spray to keep your sneakers fresh and eliminate any unpleasant odors.

Where To Buy Men's Casual Sneakers

» Quick Note: You might like this feature on J.Crew's Nike Killshot 2.

Running SneakersSerrano Sneakers: Onitsuka Tiger | New Balance Sneakers: J.Crew | Classic Sneaker: Reebok | Internationalist Sneaker: Nike | Killshot 2: Nike | Capri Triple White: Koio | Royal Blanco: Greats | Original Achilles Low: Common Projects | Wool Runners: Allbirds

Did you know that sneakers, originally called plimsolls, date back to the late 1700s? Surprisingly, during that time, there was no distinction between the left and right shoe.

I recommend a pair of sneakers with neutral shades, although a pop of color here and there can also be fun.

The bottom line: Casual sneakers feel amazing, and the right pair can add a stylish, laid-back vibe to your look.

The Minimalist Sneaker

Canvas Sneakers Inspirationcredit: Pinterest

Sometimes even the most well-dressed men like to dress casually. And with the ongoing popularity of the casual aesthetic, it's good to have a reliable casual footwear option. The canvas sneaker is perfect for all kinds of casual outings, from ball games to backyard BBQs.

Where To Buy Men's Minimalist Sneakers

» Quick Note: You might find this long-term review of Ace Marks Duke Sneaker interesting.

Canvas Sneakers

Salt Washed Sperrys: Sperry Top-Sider | Vans Washed Canvas Sneaker: J.Crew | Hermosa Plimsolls: SeaVees | The Royale Blanco White: Greats | Kurt Leather Sneaker: New Republic | Capri Triple White: Koio | Duke Sneaker: Ace Marks | Low 1 Sneaker: Oliver Cabell | Stan Smith: Adidas | Reid Full-Grain Leather Sneaker: Beckett Simonon | Veja Esplar Leather Shoe: Veja | Everyday Low Top Sneaker: Nisolo

Did you know that the original canvas sneaker (Keds) was created in 1892 by the U.S. Rubber Company? It's been said that the word "sneaker" became popularized through an advertising campaign. The shoe's rubber sole was so quiet that you could sneak up behind unsuspecting people.

I recommend choosing a pair in a neutral shade such as beige, white, or gray. This way, you won't have to think too much about what to wear them with. Minimalist sneakers in leather, suede, or canvas will always be fashionable.

The bottom line: The canvas sneaker is stylish, versatile, and a great alternative to flip-flops. It's the go-to shoe for keeping it really casual in the summertime.

» Readers' Favorite: How to Mix and Match Clothing Colors (A Master Class in Styling)


Sneakers originated in the world of athletics but have come to dominate the modern footwear market over the past few decades. Whether you're an avid gym-goer, a street style enthusiast, or simply need comfortable shoes for your morning walks, there's a pair of awesome sneakers out there for you.

Running Shoes

Packed with technological advancements and advanced cushioning, today's coolest running shoes can excel on the track, the streets, and even the runway.

Basketball Shoes

From Chuck Taylors to Air Jordans, basketball has produced some of the most recognizable and widely-worn sneakers in the world. Today, with the NBA leading the way as the most stylish sports league, it's no wonder that basketball shoes continue to dominate the fashion-forward sneaker conversation.

Skate Shoes

From the canvas-and-rubber sneakers that flooded the Venice Beach boardwalk in the '60s, to the puffy-tongued behemoths worn by mall kids in the '90s, to the hybridized sneakers worn by Olympic athletes today, skate shoes have come a long way while staying stylish. They're the perfect choice for that carefree skate rat style when paired with a pair of baggy pants.

Tennis Shoes

There's a reason why people often refer to all sneakers as "tennis shoes." The most iconic versions, like the Adidas Stan Smith and Converse Jack Purcell, are as classic and essential as sneakers can be. While they may no longer be suitable for the tennis court, these old-school styles will always ace any outfit in your wardrobe.

Good Man Brand Classic Legend London Sneaker

Sizes: 7 to 18 | Upper materials: Leather | Sole material: Leather, ethylene-vinyl acetate | Style: Lace-up

These extremely elegant leather sneakers look just as great in a boardroom as they do when you're wearing board shorts. With their clean design, combination of sporty materials, and touches of leather, you'll always look sharp whether you're pairing them with jeans and a t-shirt or a cool, casual suit.


Nike Court Vision Low

Sizes: 6 to 15 | Upper materials: Leather, synthetic materials | Sole material: Rubber | Style: Lace-up

Retro looks never go out of style, and neither do clean, white sneakers. This classic throwback to the '80s will keep you looking fresh whether you're wearing your favorite pair of jeans or shorts. Plus, Nike has updated the construction by using at least 20% recycled materials, so you can feel good about this choice. The supple leather is flexible, and the low ankle collar ensures ease of movement.

Sizes: 8 to 13 | Upper materials: Leather, suede | Sole material: Vibram rubber | Style: Slip-on

A classic pair of slip-on shoes is perfect for boat trips, barbecues, and backyard parties. Choose a pair that will last you for years. Easymocs are made in Maine and age beautifully due to their natural leather and suede construction. They can withstand anything with their durable Vibram rubber sole. Plus, they're visually appealing as well.


Rothy's The Driving Loafer

The Driving Loafer6

Best Sustainable Shoes

Common Projects Retro Low Leather-Trimmed Suede Sneakers

Retro Low Leather-Trimmed Suede Sneakers7

Best Suede Sneakers

To Boot New York Alessio Cap Toe Leather Oxfords

Alessio Cap Toe Leather Oxfords

A polished pair of chestnut oxfords can effortlessly transition from the boardroom to a fancy event. Look no further than these To Boot New York shoes for the best option.

Material: Leather

Size Range: 7-15


Best White Sneakers

Koio Capri in Triple White

Capri in Triple White3

Best White Sneakers

Tods Gommino Driving Shoes in Leather

Gommino Driving Shoes in Leather4

Best Driving Shoes

Polo Ralph Lauren Merton Leather Boat Shoe

Merton Leather Boat Shoe

These saddle brown boots are perfect for any occasion, whether it's for a board meeting or a fancy event. These shoes age beautifully and are suitable for any weather conditions.

Material: Leather

Size Range: 7-15


Best Sustainable Shoes

Thursday Boot Company Men's Captain Cap Toe Leather Boots

Men's Captain Cap Toe Leather Boots8

Best Combat Boots

Blundstone Original 500 Chelsea Boots

Sizes: 4 to 14 | Upper materials: Leather | Sole material: Thermoplastic urethane | Style: Lace-up

Chelsea boots are one of the most casual styles out there. Blundstone's rustic leather bestsellers feature a shock-absorbent and chunky lug sole, along with extra large pull tabs. Whether you're in the city or the country, these boots are both practical and cool in any type of weather.

Sizes: 7 to 15 | Upper materials: Leather | Sole material: Rubber | Style: Slip-on

Everyone loves a throwback, and as Patnoflex will tell you, this style of slip-on was favored by James Dean, Elvis, and many others. These highly-rated loafers pair effortlessly with jeans or chinos, adding a touch of polish to your casual, everyday look. And yes, they're comfortable and already broken-in for you.


Veja V-10 Rubber-Trimmed Leather Sneakers

V-10 Rubber-Trimmed Leather SneakersYou can't call yourself a sneakerhead without owning at least one pair of Veja's iconic V-10 Rubber-Trimmed Leather Sneakers. These shoes are sustainably made and incredibly comfortable, making them a must-have for any fashion enthusiast. Even members of the royal family, like Kate Middleton and Meghan Markle, are obsessed with them.

Material: Raw Materials

Size Range: EU39-EU46

When it comes to versatility, the chukka style takes the cake. It's a timeless ankle-length silhouette that can effortlessly elevate any outfit. Plus, with its welted construction, you can count on these shoes to last a lifetime.

Material: Suede

Size Range: 7-14


Best Penny Loafers

Nordstrom Pryor Penny Loafer

Pryor Penny Loafer13

Best Suede Loafers

Nordstrom Dorian Brogued Wingtip Derby

Dorian Brogued Wingtip Derby16

Best Derby Shoes

Greats The Royale

The Royale1

Best Leather Sneakers

Cole Haan Men's 2.Zerøgrand Laser Wing Oxford

Sizes: 6 to 16 | Upper materials: Leather, nubuck, suede | Sole material: Rubber | Style: Lace-up

When it comes to comfortable office shoes, Cole Haan is a reliable go-to brand. Their 2.Zerøgrand Laser Wing Oxford shoes are a work staple, effortlessly combining business style with a touch of laidback comfort. With their sporty sole and mesh upper, these shoes will keep you looking professional while feeling relaxed.


Clogs and Mules

Ever wish you could wear your cozy house shoes in public? Clogs and mules are the perfect solution, offering the comfort of slippers with the necessary support for everyday activities. Plus, they add that unique and funky energy that completes a great outfit.

Saint Laurent Wyatt Suede Chelsea Boots

Wyatt Suede Chelsea BootsEvery guy needs that one pair of boots that can be dressed up or down for any occasion. Saint Laurent's suede Chelsea boots, with their sandy color, are the perfect choice for a versatile and stylish look.

Material: Suede

Size Range: 6-17

Headshot of Sophie DweckSophie Dweck

Sophie Dweck is the associate shopping editor for Town & Country, where she covers beauty, fashion, home and décor, and more.

Sorel Ona 718 Low Sneaker

Sizes: 7 to 15 | Upper materials: Suede and textile combination | Sole material: Molded rubber | Style: Lace-up

For those who love outdoor adventures, a pair of Sorel Ona 718 Low Sneakers is a must-have. These shoes are designed for comfort, whether you're exploring the city streets or off-road terrains. With their suede and textile upper and springy foam midsole, they offer both style and functionality. You can even wear them with a suit or jeans for business travel or commuting.

Sizes: 7 to 13 | Upper materials: Leather, cotton canvas | Sole material: Rubber | Style: Lace-up

If you're experiencing foot pain, you need shoes that provide arch support without sacrificing style. Look no further than these sporty sneakers from Kuru. They feature built-in arch support to cradle your foot and provide cushioning wherever you go. Don't compromise on comfort when it comes to your footwear.

In conclusion, finding the perfect pair of casual shoes for men is essential for every wardrobe. From versatile dress shoes to comfortable sneakers and stylish boots, there are so many options to choose from. Whether you're looking for a classic and timeless style or a trendy and modern design, the list above has something for everyone. So, go ahead and step out in style with the best casual shoes that not only look great but also provide the utmost comfort.