10 Essential Shoes For Men In 2023 [+ Styling Tips]

Essential Shoes for Men - Featured Image

When it comes to a well-rounded wardrobe, shoes play a pivotal role in completing a stylish and versatile ensemble. In 2023, men’s footwear trends have taken a diverse and exciting turn, offering an array of options to suit every occasion and personal style. 

In this article, we’ll delve into the 10 essential shoes for men, along with valuable styling tips to help you put your best foot forward!

Formal Shoes

Formal shoes serve as an essential cornerstone of a sophisticated wardrobe, transcending mere footwear to become emblematic symbols of refinement and class. 

Their unique ability to exude elegance and elevate one’s look effortlessly makes them a timeless and indispensable accessory for anyone seeking to make a lasting impression.

1. Oxford Shoes

Among the array of formal shoes, the classic oxford shoe stands out as a timeless choice. These lace-up shoes boast a closed lacing system, characterised by the eyelets stitched under the vamp. The result is a clean and polished appearance suitable for any dressy occasion.

Oxford Shoes

With its sleek lines and minimalistic design, the oxford shoe is perfect for formal events, business meetings, and weddings.

Styling Tip!

To maximise the versatility of your oxford shoes, pair them with tailored suits for a sharp and professional look. For a modern twist, consider experimenting with coloured laces that complement your outfit.

2. Massage Shoes

Massage shoes are a type of comfort shoe that combine comfort and style, making them a popular choice for men on the go. These shoes often feature cushioned insoles and ergonomic designs that provide a soothing massage effect to your feet as you walk.

3. Brogue Wingtip Shoes

Brogue wingtip shoes elegantly combine classic charm with intricate detailing, making them a versatile choice for the modern man. The brogueing, characterised by delicate perforations, adds a unique touch of character to the leather upper.

Brogue Wingtip Shoes

Ideal for semi-formal events, brogue wingtip shoes also effortlessly adapt to smart-casual ensembles. Paired with tailored trousers and a dress shirt, they exude refined elegance, emphasising the balance between the decorative brogue patterns and the shoe’s sleek design.

Styling Tips!

What truly sets brogue wingtip shoes apart is their ability to be dressed down. Match them with dark jeans and a blazer for a polished yet relaxed look that’s perfect for social gatherings. 

The brogue detailing adds a subtle hint of sophistication, creating a stylish contrast with the casual elements of the outfit.

4. Monk Strap Shoes

Monk strap shoes present a distinctive departure from the conventional lace-up styles, providing a refreshing alternative that embodies both tradition and modernity.

Monk Strap Shoes

What sets these shoes apart are their unique buckle closures, which replace traditional laces and add a touch of sophistication to your footwear collection. This design detail not only contributes to their visual appeal but also underscores their practicality – a single or double buckle closure ensures a secure fit without compromising on style.

Styling Tips!

To harness the full potential of monk strap shoes, consider pairing them with tailored trousers and a crisp dress shirt. This combination instantly exudes a suave and sophisticated aura, capturing the essence of modern elegance. 

The distinct buckle closures of the monk strap shoes harmonise beautifully with the clean lines of well-fitted trousers, creating a polished look that is sure to turn heads.

Slip-on Shoes

Slip-on shoes are synonymous with convenience and casual elegance. These versatile shoes effortlessly transition from a day at the office to a laid-back evening gathering.

5. Boat Shoes

Boat shoes infuse a dash of nautical charm into your wardrobe, instantly transporting your style to sun-soaked shores and leisurely maritime adventures. These shoes are not only a fashion statement but also a practical choice, designed to withstand the demands of life both on and off the deck.

Boat Shoes

Characterised by their hallmark non-marking rubber soles and comfortable slip-on design, boat shoes effortlessly blend form and function, making them a staple for weekend escapades and casual outings.

Styling Tips!

To master the art of styling boat shoes, consider pairing them with shorts and a classic polo shirt. This ensemble strikes a delicate balance between a casual and polished appearance, allowing you to comfortably embrace the spirit of leisure while maintaining an air of sophistication.

The boat shoes’ inherent maritime charm meshes seamlessly with the relaxed vibe of shorts, creating an outfit that’s versatile enough for coastal strolls, brunch dates, or impromptu get-togethers.

When selecting your boat shoes, we recommend opting for neutral shades like tan or navy to ensure versatility and easy pairing with a range of outfits.

6. Moccasins

Moccasins are versatile slip-on shoes that embody a harmonious blend of relaxed ease and understated elegance, making them an indispensable choice for various occasions. Characterised by their soft suede or leather upper, moccasins epitomise a refined casualness that effortlessly elevates your ensemble.


The allure of moccasins lies in their ability to balance comfort and sophistication. The supple suede or leather material envelops your feet in cosiness while exuding a sense of refined taste.

This inherent versatility allows moccasins to bridge the gap between formal and informal settings, making them a go-to choice when you want to achieve an effortlessly put-together appearance without compromising on comfort.

Styling Tips!

To capitalise on the inherent charm of moccasins, consider pairing them with well-fitted jeans and a casual button-down shirt. This combination effortlessly translates into a laid-back yet stylish weekend ensemble that’s perfect for a variety of leisure activities.

The moccasins’ relaxed aesthetic complements the ease of jeans, creating an outfit that transitions seamlessly from a relaxed brunch to an afternoon stroll.

7. Penny Loafers

Penny loafers stand as a timeless classic, seamlessly bridging the gap between casual and formal attire. With their distinctive design and effortless versatility, these slip-on shoes have secured their place as a wardrobe essential.

Penny Loafers

The hallmark feature of penny loafers – a leather strap with a diamond-shaped cutout – adds a touch of elegance to their overall aesthetic.

Styling Tips!

Consider pairing penny loafers with cuffed trousers and a lightweight sweater. This ensemble exudes a polished yet relaxed aura that’s perfect for both casual and semi-formal outings.

The combination of cuffed trousers – which adds a touch of contemporary flair – and the classic penny loafers showcases a harmonious blend of timeless elegance and modern sensibility.


Boots are a wardrobe staple that adds rugged appeal to any outfit. From casual outings to outdoor adventures, boots are a highly versatile footwear option.

8. Chelsea Boots

Chelsea boots embody a sleek and minimalist design, characterised by their iconic elastic side panels that not only serve as a functional feature but also contribute to their distinct aesthetic appeal. This unique blend of form and function makes Chelsea boots a versatile and indispensable addition to any gentleman’s footwear collection.

Chelsea Boots

The hallmark elastic side panels of Chelsea boots streamline the process of putting them on and taking them off, offering an element of convenience without compromising on style.

Styling Tips!

The adaptability of Chelsea boots truly shines when it comes to styling. These boots can seamlessly transition from formal occasions to more casual settings, making them a chameleon of footwear options.

To achieve a refined look, consider pairing Chelsea boots with a suit. The clean lines and minimalist design of the boots perfectly complement the tailored silhouette of a suit, creating an ensemble that exudes both sophistication and modernity.


Sneakers are the epitome of comfort and style, offering endless possibilities for mixing and matching.

9. White Sneakers

White sneakers stand as a testament to fashion-forward choices that effortlessly harmonise with a vast spectrum of ensembles. Their pristine and versatile appearance makes them a canvas for creative styling, enhancing the modern gentleman’s ability to experiment with various outfit combinations.

White Sneakers

Whether you’re donning jeans or sporting tailored trousers, the inclusion of white sneakers instantly introduces a touch of contemporary flair, infusing your look with a dash of effortless coolness. These are the perfect choice for a casual day to the mall or your favourite trading card game shop!

Styling Tips!

To make the most of your white sneakers, consider pairing them with a variety of outfits for different occasions. For a casual daytime look, combine them with rolled-up jeans and a classic crew-neck T-shirt. This ensemble encapsulates a relaxed yet stylish aesthetic that’s perfect for weekend hangouts or coffee dates.

To elevate your white sneakers for a more polished appearance, opt for tailored trousers and a lightweight button-down shirt. This combination strikes a balance between contemporary and refined, making it suitable for casual office settings or semi-formal events.

The versatility of white sneakers allows you to seamlessly transition from day to night while maintaining a fashionable edge.

10. Casual Sneakers

Casual sneakers arrive in an array of designs and colours, catering to a diverse range of styles and personal preferences. These versatile shoes stand as the epitome of laid-back sophistication, designed to effortlessly accompany you on weekend outings and leisurely pursuits.

Casual Sneakers

Their adaptable nature allows you to explore various looks, showcasing your personality and style. From sleek monochromatic designs to vibrant patterns, the world of casual sneakers offers a myriad of options that cater to every taste.

Styling Tips!

Casual sneakers offer endless opportunities for creative styling that caters to your individual taste. For a laid-back urban look, pair your casual sneakers with slim-fit jeans and a graphic tee. The combination of comfort and style captures the essence of contemporary streetwear, making it ideal for exploring the city or running errands.

For a slightly dressier approach, consider teaming your casual sneakers with chinos and a light sweater. This ensemble strikes the perfect balance between smart and relaxed, making it suitable for casual dinners or evening gatherings.

You can also explore review platforms like Simibest to find the top local shoe brands in Singapore. Don’t be afraid to experiment with different colours and textures to add a touch of personality to your outfit!

FAQs About Essential Shoes for Men

Breaking in new leather shoes can be made more comfortable by wearing them for short periods initially, gradually increasing the duration. Applying leather conditioner can also help soften the leather and reduce friction.

It’s essential to measure your feet accurately and refer to the brand’s sizing chart. Remember that different brands might have slight variations in sizing, so trying on shoes or ordering multiple sizes can help find the best fit.

Breaking in new leather shoes can be made more comfortable by wearing them for short periods initially, gradually increasing the duration. Applying leather conditioner can also help soften the leather and reduce friction.

Boat shoes are typically worn without socks to achieve a classic, summer-inspired look. However, if you prefer to wear socks, opt for no-show or low-cut socks to maintain the shoe’s aesthetic.

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