How To Dress Smart Casual For Men | Men's Smart Casual Guide

Posted by Rishi Chullani on

In this detailed guide, we comprehensively cover how the modern gentleman can dress smart casual, so as to ensure that he is always well dressed, irrespective of occasion! 

Just when we thought we had enough to contend with regarding the vast range of men’s dress codes, the nomer ‘Smart Casual’ seems to have thrown any clarity we may have finally been reaching into utter disarray. However, there is not much to be feared or fretted over.

Smart Casual, as we will learn, is less about strict rules and more about a common thread that weaves well dressed, intentional outfits through various articles of clothing into an essentially seamless tapestry. That is, as long as there are enough articles of clothing that are formal enough and incorporated into your attire, smart casual can be reached by either dressing up casual wear or dressing down business formal attire.

And because that notion in and of itself can seem confusing, we have gone through the delightful and rigorous process of creating this fail safe, smart casual guide to help point you in the right direction. Because, as we said earlier, it’s less about rules and more about an attitude towards the whole damn thing.

Men's Smart Casual

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Introduction To Smart Casual

While business casual entails a dressing down of formal wear for occasions you would have typically dressed up for in the past (think semi-formal events, meetings outside the office, potentially date nights), smart casual encapsulates a full range of functions and occasions – and really alludes to dressing, as the name implies, ‘smarter’ across all occasions.

So how did the term ‘smart casual’ come to be? You see, in yesteryear, men’s clothing was fairly strictly defined by the type of occasion that you were dressing up for.

Dressing up for the office for your consulting, banking or marketing career? How about traditional business attire – that transitioned towards business casual at the start of the 21st century.

A strictly business meeting – you better be rocking that sophisticated suit & tie, with a pocket square to go with for added oomph and pizzaz. Heading to a bar with friends to watch the game? Most definitely casual.

However, with the relaxation of office dress codes at the turn of the 21st century, clear demarcations in men’s dress codes have become increasingly more blurred over time – resulting in the evolution of the ‘smart casual’ nomer, where formal pieces can be introduced when deemed necessary, in order to demonstrate, and more importantly, adhere to, dressing with intentionality.

Smart Casual Guidelines

That largely means:

1. First & foremost, attitude is imperative. Smart casual is less about the actual clothes you wear than it is the intentionality behind what you wear. Sounds new age-y and philosophical? Maybe, but there is little room for quackery on this blog! Whilst we often detail guidelines for how to dress well – intentionality is absolutely key with dressing smart casual.

Hence, while jeans may be considered casual, chinos with a sports jacket business casual and a suit formal wear, smart casual is about how you wear these items – hence, you can have smart casual casual attire / try saying that over and over really fast, smart casual business casual, which in some ways, is a redundant use of the phrase, and smart casual formal attire – which sounds countertuitive but in fact can work – think clean white sneakers with a suit.

Men's Smart Casual

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Given the above and how it is possible to transition from a traditional realm / delineation of clothing to smart casual, it is apt to discuss smart casual wear being on a spectrum, and not a binary on / off type of dress code, given how versatile it is and how seamlessly it can be integrated into the more traditional casual / business casual / formal style parameters that we’re used to thinking of men’s style within.

2. Keep things simple and eliminate confusion! While this may seem like a summary of the points below, we think it is worth mentioning as a separate note of importance. Stick to tried and tested wardrobe essentials that would generally be deemed on the smarter end of the clothing spectrum – think dark denim, chinos, oxford dress shirts, simply knitwear for sweaters and unstructured blazers – unstructured blazers may not be something one typically thinks of with respect to smart casual wear – but the loosening of shoulder pads allows you to look smartly dressed without the more overt formality associated with a typically structured blazer.

Men's Smart Casual

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3. Build up or build down. As mentioned above, smart casual encapsulates a mindset more than hard and fast rules. Strutting a casual ensemble, including say – a bomber jacket, jeans, t-shirt and trainers? Replace the jeans with chinos and your half way there. Replace the trainers with smart, sleek sneakers, and you’re firmly in smart casual territory. Conversely, dressed up in a suit? Lose the formal silk tie and replace the oxford dress shoes with smart chukkas and voila, you have strutted into smart casual attire land.

Men's Smart Casual

Building down from business professional attire is one way to enhance your smart casual game! Courtesy of

4. Embrace complementary colors. Given that you are likely to wear separates when transitioning from business formal to smart casual (i.e mismatched blazers & trousers), stick to complementary neutral colors – such as classic mid grey woolen trousers paired with a navy sports jacket and a white t-shirt. Alternatively, you can adopt earthy tones such as olive green, khaki or brown.

Men's Smart Casual Earth Tones

Neutral and earth tones are an incredible way to pull off the perfect smart casual look! Courtesy of

5. Add elements of shade (to casual wear) or specks of tint (to formal wear). As a general guide, darker colors lend themselves to a more formal look, whilst lighter colors accentuate a more casual style. Hence, when dressing smart casual, adding a darker article of clothing to your casual wear will elevate your aesthetic to smart casual. Conversely, replacing a darker article of clothing with a lighter article of clothing will enhance the casual nature of a more formal outfit.

Examples include replacing regular blue denim with darker navy or burgundy chinos to transition from casualwear to smart casual. Alternatively, replacing a darker suit with a lighter blue linen suit will help transition a formal ensemble to a more smart casual look.

Men's Smart Casual

Incorporating lighter colors into your ensembles that would typically be classified as business professional will help transition them towards the smart casual end of the spectrum. Courtesy of www.luxedigital

6. Embrace the blazer / sports jacket. You’ve heard of adopting the blazer for your business casual look, and it would almost seem like a pre-requisite. Don it with a pair of dark denim, however, and you’re well on your way to smart casual attire. Looking for something dapper but ‘casually relaxed’ at the same time? Opt for an unstructured blazer, where a lack of shoulder padding makes for a distinctively smart casual look!

Blazers Smart Casual Attire

Blazers can become an integral part of your smart casual attire. Courtesy of

7. Where possible, replace t-shirts with buttoned shirts. During the summer months, this would entail conjuring up your polo dress shirts. These shirts, as the name suggests, were originally worn for playing the game of polo. Ditto for the button down collar, which was designed so it didn’t flap around during those oh-so heated polo wars of attrition. As such, upgrading to a polo shirt immediately adds an element of formality to one’s attire.

During the fall & winter seasons, this would be best served by incorporating buttoned down oxford dress shirts within your attire. The buttoned down oxford dress shirt, a more informal variation of your traditional collared dress shirt, is perfect for incorporating as part of a smart casual getup.

Men's Smart Casual Buttoned Down Dress Shirt

Buttoned down collared dress shirts provide for the perfect addition to your smart casual attire! Courtesy of

8. Make Chinos a staple! While dark denim will certainly land you within the smart casual realm, chinos are considered a more fail safe way of adding formality to your attire, hence elevating casual clothing to the smart casual genre.

Men's Smart Casual Chinos

Chinos are a truly inspirational way to transition towards smart casual. Courtesy of

9. Adding textural variation. Whilst we often discuss the dressing up of casual clothing, elevating it to smart casual attire, textural variation works best with the inverse. That is, replacing formal textures with a suit, for example, with a fabric that has more textural depth, such as tweed. This replacement of fabrics, especially when worn as part of a separates attire (non identical suit jackets and pants) can help transition an ensemble from formal to smart casual.

Men's Smart Casual Tweed

A tweed jacket provides the perfect level of textural variation for a smart casual ensemble! Courtesy of


10. And finally, and just as (if not more important) – get your details straight! Paying attention to all the elements – such as appropriate trouser length, well polished shoes / sneakers and wearing matching leathers can go a long way towards creating the coveted smart casual look.

Men's Bracelets | Leather Bracelets | Beaded Bracelets

Given the above, we think breaking down smart casual versus its more or less formal counterparts will further help distinguish this fast rising genre:

Smart Casual Vs Formal Attire

Given that we are reading this blog, we hopefully all know what constitutes formal wear. Typically comprising of a darker colored suit, lighter colored white or light blue dress shirt, a darker colored tie, and formal dress shoes such as oxford cap toes, a formal look is considered as such from head to toe.

Smart Casual will entail replacing one of these elements with less formal attire. That could mean

  • Replacing the dress shoes with smart, streamlined and sleek plain white sneakers
  • Replacing the traditional silk tie with a textured knitted tie, taking away some of the sheen from the accessory but adding a strong element of textural variation
  • Replacing the suit look altogether with separates that entail a more coarse jacket (e.g tweed) and pants – helping to create a more ‘smart casual’ look that isn’t defined by the parameters of a traditional woolen suit.

Men's Smart Casual

Adopting a lighter colored suit and strutting a pair of perfectly sleek sneakers will help you seamlessly transition from business formal to smart casual attire. Courtesy of

Smart Casual vs Business Casual

While the lines between smart casual and business casual are seemingly blurred, nuance is critical when differentiating between the two. Business casual typically involve the more formal parts of men’s attire, without being overtly formal i.e well fitted chinos, dressier shoes and a tucked in dress shirt.

So how does one transition from business casual to smart casual? Given that smart casual is on the more ‘casual’ end of the spectrum, this would entail swapping out some of your more formal pieces of attire for articles of clothing that are more casual. Examples include:

  • Replacing dress shoes with streamlined white sneakers or loafers
  • Replacing your business casual dress shirt with a buttoned up polo. Still well dressed, but now on the ‘smarter’ end of the spectrum!
  • Replacing the traditional leather belt with a textured, fabric belt.

Men's Smart Casual vs Business Casual

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Smart Casual vs Dressy Casual

Who knew this term existed? Yes, we do occasionally see the ‘dressy casual’ code inscribed on fancier wedding invitations – and it essentially alludes to formal wear sprinkled in with elements of casual attire. An example would be a linen suit worn to a beach wedding.

Looking to casualize (is that a term?!?) your dressy casual linen suit? Try one or both of the following:

  • Replace your white button down shirt with a plain white crew neck t-shirt
  • Replace your brown dressier brogues with plain white sneakers

Men's Smart Casual Linen Suit

Introducing a white t-shirt and sneakers helps transition this dressy casual linen suit attire to the perfect smart casual getup! Courtesy of

Smart Casual vs Casual

While casual outfits, by definition, consist entirely of less formal elements gulp!), a smart casual transition would involve introducing some more formal elements, such as replacing regular blue jeans with dark denim, your sneakers with dressier brogues or your t-shirt with a polo.

Men's Smart Casual

This stunning infographic perfectly encapsulates smart casual attire, especially as compared to casual attire. Courtesy of

How To Dress Smart Casual By Season

While understanding how transitioning to smart casual works, having an idea by season will provide you with a full arsenal of options the next time you’re looking to elevate your look.


Instead of dressing in your standard jeans and tee, about how slipping on a linen jacket with a pair of chinos and some sleek, streamlined white sneakers for a truly smart casual ensemble. Replace the t-shirt with a seersucker shirt for some textural variation.

This type of ensemble will provide you with different options based on weather, and allow you to strut your stuff sans linen jacket if needed.

Men's Smart Casual Spring Season

A stunning spring season smart casual look! Courtesy of



That enervating summer heat makes layering increasingly difficult, especially when weather starts getting into the 90’s. With that said, drop the jacket unless you really feel the weather permits. Replace your traditional jeans / shorts and tee look with lighter colored chinos, an untucked linen dress shirt and a pair of white sneakers or loafers!

And with that, you have weather appropriate clothing that will allow you to deflect heat, all while making that quantum leap from casual to smart casual during summer months!

Men's Smart Casual Summer

Lighter colored chinos and a linen shirt make for ideal summer smart casual attire! Courtesy of 


Fall, the perfect season for layering – as discussed many times in this blog, makes for an opportune time to transition your clothing from casual to smart casual.

Fall season is perfect for building up your ensemble from the bottom up. How about opting for some suede Chelsea boots, chino trousers and a v-neck sweater? Throw on a vest jacket or sports coat, and you’ve got the perfect smart casual fall ensemble!

Men's Smart Casual Fall Attire

Impeccable, perfectly layered smart casual attire for the fall season! Courtesy of


Winter, like the fall season, provides ample opportunity for the layering of clothing. However, with colder weather, one naturally has the inclination towards additional layers, beyond even what the fall season may permit! As such, throwing on a ‘smarter’ looking outer layer, such as a peacoat or longer winter overcoat can do a great deal to accentuate that dapper, smart casual aesthetic.

Men's Smart Casual Winter Attire

Smart Casual attire for winter season will typically involve more layers! Courtesy of

Smart Casual Key Pieces

Here are some great key smart casual articles of clothing that can often be used interchangeably to create that snazzy look!

Button Up vs Button Down Shirts

While not much is often made of the difference between button up and button down shirts, the differences can be stark. Button down dress shirts are typically associated with more formal dress codes, which usually refers to a shirt with a placket of buttons. A button down shirt typically doesn’t have a placket of buttons, but has buttons for fastening down the collar of the shirt. Buttoned down collars are typically less rigid, as they aren’t presented with an opening for collar stays, (that help maintain collar firmness).

 Men's Smart Casual Button Down Shirts

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Blazers or sports jackets are an absolutely essential in every dapper gentleman’s wardrobe, and even more so when regarding smart casual wear. Blazer jackets are perfect for dressing up a smart casual ensemble, or when used as separates to dress down a more formal, business professional getup.

Men's Smart Casual Blazer

Blazers are an absolutely integral component in any smart casual wardrobe! Courtesy of

Merino Wool Sweaters / Cardigans

Finer outer layers, such as a merino wool sweater or cardigan, are ideal for adding depth to a casual look and elevating it to smart casual attire, without bringing on any of the bulkiness that comes with heavier fabrics, such as a cable knit sweater.

Men's Smart Casual Sweaters

Finer sweaters allow for that perfect, preppy smart casual attire! Courtesy of

Dark Denim / Chinos / Wool Trousers

If opting for denim with your smart casual attire, we strongly suggest going with dark denim. While traditional, lighter blue denim is a definite no no for business casual or smart casual attire, dark denim that is well fitted is perfectly acceptable within the smart casual realm. Please note that when opting for jeans, it is best to go for a streamlined, sleek silhouette without any unnecessary adornments.

Chinos are the perfect bridge between casual denim and pants, and will allow you to dress smart and dapper without looking overtly formal. Chinos can be worn year round during both warm and cooler seasons, given their insulative properties. Fabric composition for your pants during the summer months is extremely important. Linen, while lightweight and breathable, wrinkles easily. Cotton is largely considered inexpensive and is widely available, and helps with absorbing of moisture.    

Men's Smart Casual Chinos 

It's hard to go wrong when chinos are incorporated into your smart casual attire! Courtesy of


While shoes are incredibly important for any set of men’s attire, they may become even more prominent with smart casual getups. With smart casual attire, it is often the shoes that help tip the ensembles from formal or business casual into smart casual land.

When discerning between footwear options, it is therefore extremely important to strike an appropriate balance between style, comfort and the degree of formality you are looking to dress with. We should therefore breakdown potential smart casual shoes into several categories:

Dress Shoes

Dress shoes are considered a classic and versatile choice for smart casual attire. Leather or suede shoes in traditional classifications of oxfords, brogues or wingtips should work perfectly. Dress shoes can help to add a suave and sophisticated touch to your overall attire.


Loafers offer the perfect balance of comfort and style, making them ideal for smart casual wear! Whether your loafers are of the leather or suede variety, either will suffice as long as they are of a sleeker silhouette. Strut them with well fitted trousers, chinos or even dark denim!

Sleek Sneakers

While you can reserve your more colorful sneakers for truly casual attire, streamlined, sleek white sneakers are ideal for smart casual ensembles, whether they are of the leather or canvas variety!


Depending on season and personal preferences, boots can be a great addition to your smart casual attire. Whether you are strutting Chelseas or Chukkas, either can help add a touch of rugged sophistication to your look. In our opinion, boots work best with dark denim and chinos – though they can work with trousers. The more formal the choice of trousers, the more sophisticated these boots should be.

Men's Smart Casual Footwear

Boots, dress shoes and sneakers are all viable options for a dapperly done smart casual ensemble! Courtesy of

Key Smart Casual Sets

Bringing it all together, here are some great looks to pull off with your smart casual attire!

Elevated Casual Wear

As mentioned in one of our earlier points – sometimes you need to simply just build up from where you are. Incorporating casual articles of clothing that you are already comfortable with, but with more luxurious fabrics, will go a long way towards elevating your ensembles towards smart casual status. Bomber jackets in suede or leather, t-shirts in merino wool or softer, cashmere knit sweaters will instantly elevate your aesthetic. Combine with chinos and derbies for a perfect bookended look!

Men's Smart Casual

Elevated casualwear! A key way of dressing smart casual! Courtesy of

Blazer with Jeans / Chinos

Ahhh yes, the absolute necessary men’s wear staple. As mentioned above, employing an unstructured blazer with looser shoulder padding will lend itself towards a more ‘smart casual’ look, versus the traditionally padded shoulder stiffness associated with blazers. Keep your denim dark and fitted, or better yet, slap on a pair of chinos and streamlined, sleek white sneakers for a great, elevated look.

Men's Smart Casual

We may have hammered home this point repeatedly. But its worth mentioning again. Few items attest to smart casual attire like chinos and a well matched blazer. Truly, truly dapper. Courtesy of

Pocket Squares | Silk Pocket Squares | Linen Pocket Squares


Splitting up tailoring in separates has long been a way of making a suit more casual. By embracing two separate, mismatched pieces of tailoring, you automatically relax the business professional vibes with traditional suiting attire.

Similar to the above combination, but with more variety, employing separates as part of your smart casual game will allow you to mix and match with a variety of colors and fabrics. Think brown corduroy pants and a blazer, or an unstructured blazer with white linens.  

 Men's Smart Casual Seperates

Separates, or deliberately combining mismatched trousers and jackets, are an ideal way to embrace the smart casual paradigm! Courtesy of

Shirts & Knitted Sweaters

Yes, that classic ivy prepster look has made its way onto this list. One of our traditional favorites, this involves wearing a dress shirt under a knitted sweater. Please note that we would eschew heavier knits such as cable knit sweaters (as these generally have more casual connotations) in favor of finer knitwear, such as a crew neck, v-neck or cardigan sweater.

Men's Smart Casual Sweater

That classic, preppy look!  Courtesy of

White T-Shirts

While we are strong advocates of white buttoned up or down dress shirts with your smart casual wear, a well cut white t-shirt is hard to beat when worn under a lighter weight, unstructured suit. However, during the Fall season, a knitted polo or fine sweater can also do the trick!

Men's Smart Casual

White t-shirts provide for effortless, timeless smart casual style. Courtesy of

Ditch The Traditional Silk Tie

Yes, that’s right, we said it. Ditch the traditional silk tie! While a silk tie can look incredible within a business professional or business casual format, we do think that eschewing your silk tie in favor of either a loosely knotted knit tie, cotton, novelty polyester or sans tie, is the way to go with your smart casual attire. Alternatively, strut a silk or linen pocket square, with hand rolled contrasting edges for added effect!

Please feel free to view The Dark Knot's stunning range of silk knit ties

Please feel free to view The Dark Knot's exquisite range of floral cotton ties

The Dark Knot's sublime array of novelty polyester ties can be viewed here.

Men's Smart Casual Knit Ties

Knitted Ties with Smart Casual Wear? Sign me up all day, everyday! Courtesy of

Knit Ties | Silk Knit Ties | Knitted Ties

White Pants

No, you don’t need to be inspired by the 90’s Miami narco trade to be strutting white pants. And they certainly don’t need to be super tight. White trousers can certainly form the foundation of a great smart casual getup, providing both a relaxed, yet dapper smart casual vibe that is bound to elicit head turns!

Men's Smart Casual White Chinos

Too damn difficult to pass up! It is imperative that white pants make their way into every dapper gent’s smart casual wardrobe! Courtesy of

And that’s a wrap for this one! We hope that you have enjoyed reading this as much as we have writing it!


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