Stay Comfortable With These 16 Best Casual Shoes For Men

best casual shoes for men

Far from just means to cover your feet, shoes in today’s fashion world can make or break an outfit! Why not change up your footwear game with a pair of fashionable casual shoes? Excelling in both style and functionality, shopping for casual shoes for men can be rather challenging given the sheer variety of brands and types of footwear available. To nudge you in the right direction, here are a couple of the best casual shoes for men including slip-on shoes, sneakers and boots!

Best casual shoes for men: Smart-casual 

1. Timberland Men’s Port Union Waterproof Oxford 

timberland oxford best casual shoes for men
(Credit: Timberland Official Store)

Looking for the best smart-casual shoes for men that balance comfort and style? Timberland Men’s Port Union Waterproof Oxford (available on Timberland Official Store) is a good start thanks to its premium fabric lining that is made of 50% recycled plastic. Comfort-wise, this Timberland shoe has incorporated an AeroCore energy system for impact cushioning and a breathable mesh lining. The end result is a smart-casual shoe for men that complements any social occasion!

2. Clarks Step Welt Free

clarks casual shoes for men
(Credit: Clarks Singapore Official Store)

When it comes to men’s smart-casual shoes that can complete any look, few options can rival the Clarks’ Step Welt Free (available on Clarks Singapore Official Store) from their Cloudsteppers collection. Based on the collection’s name, you know you’re in for a treat in terms of sole comfort. These Clarks shoes rely on Cushion Soft technology and OrthoLite foam inlay to make each step feel extra light! Without compromising comfort for style, these lace-up kicks make the best casual shoes for men in Singapore! 

3. Vans Old Skool

vans old school smart casual shoe
(Credit: Sports-Zone SG Official Store)

It’s impossible to talk about the best men’s smart-casual shoes without mentioning Vans Old Skool (available on Sports-Zone SG Official Store)! Adored by fans for its affordability and sheer range of designs, this classic piece of skatewear debuted the famous Jazz Stripe – a single squiggly line at the side of the shoe. At less than $90, it’s perfect for guys looking for casual shoes for men while on a budget. Given their wide range of stylish colours and limited edition patterns, you’ll definitely find a pair that fits your dress style!

Best casual shoes for men: Slip-ons (loafers) 

4. Vans Classic Slip On

Vans Classic Slip On

Vans is also well known for their slip-on shoes for men, otherwise known as loafersSpecifically, we love their standard Vans Classic Slip On (available on LEFTFOOT SG) which is acclaimed worldwide for its comfortable silhouette, easy wearability and beloved design. On top of its durable rubber waffle outsoles, this slip-on shoe for men also includes supportive padded collars and elastic side accents which adds to its overall comfort. That’s a win in our book! 

5. Geox Men’s Loafers

Geox Men’s Loafers
(Credit: GEOX Official Store)

If you’re struggling to find a pair of the best casual shoes for men that are breathable yet stylish, look no further than Geox Men’s Loafers (available on GEOX Official Store). This pair of Geox slip-on shoes for men has a premium rubber sole that features a waterproof membrane, allowing for natural temperature regulation on the feet. This creates the perfect microclimate inside the shoe and will keep your feet dry and comfortable the entire day – even in Singapore’s sweltering weather!

6. Polo Hill Men’s Moccasins Loafers

polo hill casual shoe for men
(Credit: POLO HILL Official Store)

As one of the best pair of casual shoes for men, the Polo Hill Men’s Moccasins Loafers (available on POLO HILL Official Store) definitely stands out among the sea of slip-on shoes for men. This pair of Polo Hill shoes come in black or brown, which works best at any smart-casual event! Other than its aesthetics, it is fitted with a lightly padded footbed that makes walking comfortable and gives support for your heels too. Additionally, its outsole is made of polyurethane which provides great wear and tear resistance.

Best casual shoes for men: Sneakers 

7. Converse Chuck Taylor All Star Ox

Converse Chuck Taylor All Star Ox
(Credit: Converse Official Store)

Ready for a blast from the past when it comes to the best casual shoes for men? Converse’s Chuck Taylor All Star Ox (available on Converse Official Store) will certainly win you over with their modernised take on the old-school Chuck design! To stay true to its roots, the shoe maintains its original silhouette to enhance its vintage charm. Converse has incorporated a premium organic canvas and 35mm rubber heel taping which doubles down on comfort levels. This winning combination will make you reach for this pair of Converse shoes for any casual occasion.

8. FILA Tracer Chunky Sneakers

FILA Tracer Chunky Sneakers
(Credit: FILA Official Store)

Contrary to today’s sneaker culture of slim silhouettes, the FILA Tracer Chunky Sneakers (available on FILA Official Store) stays true to its name with its bold retro inspired design! While such a chunky and loud appearance might polarise sneakerheads, it’s undeniable that this casual sneaker for men is built with quality in mind. The ultra thick rubber outsole grants wearers better grip and stability compared to regular sneakers while the midsole is designed to be both durable and lightweight. Overall, this FILA men’s sneakers would make a nice addition to any shoe collection given its reasonable price and unique aesthetic!

9. New Balance 500 Classic Men’s Sneakers

New Balance 500 Classic Men’s Sneakers
(Credit: New Balance SG Official Store)

From minimalist designs to bold patterns, New Balance takes great pride in showcasing their best-selling pair of casual shoes for men! Investing in a pair of New Balance 500 Classic Men’s Sneakers (available on New Balance SG Official Store) will grant you a good balance (no pun intended) of comfort and style. New Balance incorporates their proprietary ENCAP sole technology for increased support and stability along with a mix of suede leather and mesh to provide breathability and style. It’s no wonder fans have been rocking these New Balance shoes since the 1980s!

10. Adidas NMD

Adidas NMD - casual sneakers for men
(Credit: Sport Planet Warehouse Outlet)

With a staggering number of colourways and nods to previous Adidas sneaker models, Adidas NMDs are legendary in today’s pool of casual shoes for men. For each of these Adidas men’s sneakers, the German designers struck a perfect balance of quality materials with premium workmanship. In particular, this pair of sleek NMD R1 (available on Sport Planet Warehouse Outlet) sneakers incorporate both style and comfort and will especially be a treat for sneakerheads!

11. Adidas Stan Smith

Adidas Stan Smith
(Credit: adidas Official Store)

Hailed as one of the most influential sneakers of all time, Adidas Stan Smith (available on adidas Official Store) have exploded in popularity recently and remain a respectable option in the world of casual shoes for men! Winning over the masses with its elegant lines and low profile design, the Adidas Stan Smith sneakers have even been endorsed by stars like Ellen Degeneres and Pharrell Williams. Since its reintroduction in 2014, numerous variations have popped up on the market, from suede and knit versions to featuring a limited edition Marvel’s Hulk design— as in the model pictured above!

12. Nike Flyknit Racer

Nike Flyknit Racer casual sneaker for men
(Credit: SneakersClinic)

Renowned for their eye-catching design, Nike Flyknit Racers (available on SneakersClinic) remain a popular choice when it comes to the best casual shoes for men! Featuring a feet-hugging Flyknit material that is more flexible and breathable, the Flyknit Racers will grant you an unmatched level of airflow and weightlessness. This is also a bold style that pairs well with joggers or jeans. Whether you’re doing some light running or heading out to town, you’ll enjoy the comfort and versatility provided by this popular Nike shoe model!

13. Macbeth PRIA

best casual shoes for men macbeth pria

The Macbeth PRIA (available on not only sports a sleek and stylish design but also helps to advocate sustainability in footwear! The Macbeth brand was founded in 2002 by Blink-182 vocalist Tom Delonge, whose mission was to produce a vegan collection of recycled canvas shoes and footwear. As such, Macbeth shoes are made with organic canvas from processed vegetable fibres, natural rubber, and water-made glue, giving them superior flexibility and enhanced comfort while walking in them.

Best casual shoes for men: Boots 

14. Dr. Martens 1460 Boots

Dr. Martens 1460 Boots
(Credit: Dr. Martens Singapore Official Store)

Men’s boots might not be the first thing you think of when it comes to the best casual shoes for men in Singapore, but we assure you that they can be just as comfortable and stylish! Case in point: this pair of Dr. Martens 1460 Boots (available on Dr. Martens Singapore Official Store) that are a common sight among today’s streetwear enthusiasts! Given the brand’s rich history, this pair of Dr. Martens boots have garnered a large following over the years for their classy yet rugged aesthetic. But it’s not all just about the looks here. Their unique air-cushioned ‘Bouncing Soles’ also prove to be a huge plus for comfort!

15. Timberland Men’s Waterproof Boots

Timberland Men’s Waterproof Boots
(Credit: Timberland Official Store)

Another frontrunner on our list of best casual shoes for men has to be this pair of Timberland Men’s Waterproof Boots (available on Timberland Official Store) which stands out for its instantly recognizable colour and design. This pair of Timberland boots also features a down-free PrimaLoft insulation and a padded collar for a comfortable fit around the ankle. This guarantees comfort and gives your feet the necessary support for a full day of wear.

16. Caterpillar Men’s Second Shift Boots

Caterpillar Men’s Second Shift Boots
(Credit: N-Zone Sports Official Store)

Those who think that the best casual shoes for men are not durable obviously haven’t seen this pair of Caterpillar Men’s Second Shift Boots (available on N-Zone Sports Official Store) that delivers comfort and durability to get you through your day. Its rugged styling and quality leathers make this boot a popular choice among fashionistas. This pair of Caterpillar boots also come with a rubber outsole that is designed to be slip-resistant for optimal traction. 

Walk the talk with these best casual shoes for men

From slip-on shoes to casual boots, you’ll certainly be spoilt for choice when buying the best casual shoes for men with us! Bought something from our list of recommended casual shoes for men but unsure about how to best style them? Why not refer to our list of trending men’s fashion styles in Singapore for some styling inspiration! Don’t forget to equip yourself with some of the best men’s wallets to up your fashion game too. If you want to smell as good as you look, then check out our list of best mens’ perfumes which will leave a lasting fragrance! 

This article was updated on 4 January 2022. Additional research was done by Gabriel Choo.