How to Master Smart Casual Style + 13 Outfit Ideas for Men

I love smart casual style because it’s one of the few styles that you can wear almost anywhere and be appropriately dressed.

I think it’s imperative to dress for the occasion, in fact I believe that it’s the most important element of timeless style. When you’re not dressed for the occasion, you look ill-prepared no matter how presentable you may appear.

With this in mind, we’re going to talk about smart casual style as it pertains to the modest man. But first, let’s define smart casual.

What Exactly Is Smart Casual Style?

Here’s how the dictionary defines smart casual:

Neat, conventional, yet relatively informal in style, especially as worn to conform to a particular dress code.

This somewhat explains it, but it doesn’t get into is specifics. What exactly is ‘conventional’ and what is the ‘particular dress code’?

First off, it’s not business casual. The two terms have some overlap, but I like to think of business casual as dressing smart at work, whereas smart casual is dressing smart no matter the occasion.

It’s a little confusing because when it comes to smart casual style, jeans can be smart and a blazer can be casual. How so? Well a pair of slim fitting dark wash jeans are a smart casual staple and a blazer with a textured fabric like tweed or linen leans casual even though it’s still considered smart. In these cases, the shade and fabric determine the formality.

This is why smart casual style can be tricky. And to further muddy the waters, who is the judge of what is considered smart or what makes a particular garment casual? Ultimately it comes down to preference as it differs from person to person.

My take on it is that smart casual style is a happy medium between being dressed up and dressed down. And since it straddles the fence between both spectrums of formality, that makes it one of the most versatile and best styles for any guy.

How to Nail the Smart Casual Aesthetic

The best way to nail the smart casual aesthetic is to swap smart pieces for casual ones and vice versa so that there’s a balance of smart and casual garments in your getup. It takes time, but after a while you get a feel for what’s casual and what leans smart.

See Also: Sweater for Shorter Men (In-Depth Guide)

A prime example is wearing a sharkskin suit with sneakers. A sharkskin suit is ultra formal, thus smart and a pair of white sneakers are quite casual. That’s a 50/50 balance and thus a perfect smart casual look. This type of contrast in formality allows for it to work. If you’re leaning too far in one direction, it’s not so much a balance of smart casual, but rather just smart or casual.

I’d say, if you have a pretty firm grasp on your personal style and what makes up good style then trust your instincts and use your best judgement. Don’t think too long and hard about it. If it feels right, it probably is and vice versa.

In the end smart casual has been said to be a mood or an attitude rather than just the amalgamation of individual articles of clothing.

As a refresher, I put together some bullet points on dressing taller and some key elements of smart casual style.

Key Elements of Dressing Taller

• Nail the fit (slim and fitted, not ultra skinny and definitely not baggy)
• Wear accessories like pocket squares, scarves, tie bars, neckties, hats, slim jewelry, etc. to avert the gaze towards your face
• Streamline your look (avoid unintentionally cutting yourself in half and stark contrast)
• Embrace monochrome looks (darker colors create an illusion of lengthening, extending, and slimming)
• Rock boots to add height
• Wear pants with no break to streamline your look
• Get your pants tapered towards the ankle (this makes a world of difference)
• Mind your proportions (wear accessories in proportion with your build)
• Wear small scale patterns
• Higher rise pants can raise perceived waistline, making for a longer leg line)
• Be confident

Key Elements of Smart Casual Style

• Emphasis on tailoring
• High-low aesthetic (e.g. trainers & sharkskin suit)
• Embrace simplicity and minimalism
• Dark color schemes (lean more formal and thus smart)
• Texture (wool, tweed, flannel, linen)
• The blazer (single easiest way to smarten up a casual look)

Now that we’ve gone over some key elements of dressing taller and smart casual style, let’s go over some visual examples.

Each of the styles in this lookbook will contain several of the above elements.

Look #1: The Casually Sueded

For the first look, it’s pretty simple. I styled the suede bomber jacket up top and the suede chelseas down low.

In-between I went with dark gray wool trousers and a burgundy sweatshirt with an attention grabbing floral print. It’s a good balance of smart and casual.

• Suede bomber jacket = smart/casual
• Floral sweatshirt = casual
• Tailored trousers = smart
• Suede chelsea boots = smart/casual
• Scarf = smart (functional piece)

This first look and the following two lean more casual on the smart casual scale.

Look #2 & #3: The Casually Tailored v1

For the second look I replaced the suede chelseas with white trainers and the sweatshirt for a clean, fitted white tee.

The tailored trousers and white sneakers make for a bit of a high-low move.

• Suede bomber jacket = smart/casual
• White tee = casual
• Tailored trousers = smart
• White trainers = smart/casual
• Argyle socks = smart

Everything’s pretty much casual here as the woolen trousers are working hard to smarten up the overall look.

Look #2 & #3: The Casually Tailored v2

For a third look I switch up the bomber for a smart casual staple, the navy harrington jacket. I also swapped the all white trainers for another casual sneaker with a gum sole which works well with casual looks. The jacket and trousers combo is smart in my opinion.

• Harrington jacket = smart/casual
• White tee = casual
• Tailored trousers = smart
• White sneakers = casual
• Argyle socks = smart

If you’re concerned with cutting yourself in half visually you can swap the white tee for a dark gray tee, similar in color to the pants for a more streamlined look.

Look #4 & #5: The Office Uniform v1

Elevate your office style with a fresh pair of walnut double monk straps and a relaxed blazer. The jacket looks like a normal blazer, but it’s much more casual due to the sweatshirt material and patch pockets.

Underneath I’ve got a denim looking chambray button down shirt and down low I’m wearing a pair of dark gray, slim fit corduroy pants.

• Cotton blazer = smart/casual
• Chambray shirt = casual
• Corduroy slim pants = casual
• Double monkstraps = smart
• Argyle socks = smart
• Pocket square = smart

I’m also wearing argyle socks and added a blue zig zag line patterned pocket square with a clean Presidential fold to finish the look.

Look #4 & #5: The Office Uniform v2

Maybe the walnut shade double monk straps are too bold for your taste. You can tone it down with a pair of brown cap toe boots. In another switch up, I added a purple argyle sweater, not a color you see too many guys wearing. It’s a smart casual move that adds a little texture and pattern to the look.

• Cotton blazer = smart/casual
• Chambray shirt = casual
• Argyle sweater = smart/casual
• Linen pocket square = smart
• Corduroy slim pants = casual
• Plain toe boots = smart/casual
• Argyle socks = smart

If you want to smarten it up even further, I like to wear a necktie with v-neck sweaters. Finally I added a linen pocket square with purples accents that pick up the purple of the sweater and tie (seen here in the video).

Look #6: The Spring Blues & Brown

There’s a saying “no brown in town,” but I’m all for it.

Here I’ve paired a brown leather jacket with a blue chambray button down and navy chinos. And finish the look off with navy suede chukkas.

• Leather jacket = smart/casual
• Chambray button down = casual
• Navy chinos = smart
• Suede chukkas = smart/casual
• Sunglasses = smart (functional piece)

Brown and blue is one of my favorite color combinations and it works really well for most guys. Modest man or not, this is a color scheme most guys can pull off.

Look #7: The Simple Summer

This is a refined summer look. I’m rocking a pair of tailored trousers. They’re actually suit pants for a Prince of Whales double breasted suit I have, but I love wearing them as a separate.

Up top I have a well fitting gray polo in a luxe touch cotton and finish the look off with brown suede loafers and matching belt with gold trim.

Polo shirts are a level above a standard t-shirt. They’re sporty and give a refined edge, especially when paired with tailored trousers. Also notice no break of the pants which is appropriate for shorter guys.

• Polo shirt = smart/casual
• Tailored trousers = smart
• Suede loafers = smart/casual
• Suede belt = smart/casual
• Watch = smart (functional piece)

If you want to simplify things, you can lose the belt and untuck the front of the shirt. It’s much more casual and relaxed, but still smart because of the polo, dress slacks and loafers combo.

Look #8: The Dressed Denim

With this look, I smarten up a light wash denim jacket with a necktie and tartan patterned button down shirt.

The solid, rich colored necktie picks up the burnt orange from the shirt while the green woolen trousers pick up the green from the shirt.

Overall, it’s a harmonious look that’s dressed up, but made casual with the denim jacket. There’s also an emphasis on tailoring as the wool trousers taper towards the ankle.

• Denim jacket = casual
• Tartan button down shirt = casual
• Necktie & tie bar = smart
• Woolen trousers = smart
• Suede chelseas = smart/casual

The versatility of the chelsea boots is on display as it works well with or without the denim jacket.

Look #9: The Fall Staples

With this look, I’ve incorporated a few of my favorite fall staples of the moment.

You’ll notice I’m wearing the green wool trousers from the previous look (one of my favorite fall/winter colors) and swapped the button down tie combo for a lightweight turtleneck sweater which is a great alternative to the shirt and tie look.

Since the rollneck is a darker color I think it pairs well with a darker shade denim jacket. Keeping with the darker theme, I also opted for dark navy suede boots down low as well.

• Denim jacket = casual
• Turtleneck sweater = smart
• Woolen trousers = smart
• Suede cap toe boots = smart/casual

Overall, this is how you can dress up a denim jacket or dial down the formality of the rollneck and tailored trousers. Either way this is a classic smart casual getup.

Look #10: The Rule Breaker

Of course once you know the rules, you can go ahead and break them, with intention.

This look you might say is more rugged if anything and while that’s true, it’s also smart depending on the situation. Context is key.

Overall this look is looser fitting all around. The jeans are a bit wider throughout the leg, the cuff is thicker and the heavy button up has a large square pattern and is quite relaxed.

For my shoes, I’m wearing a pair of rugged moc-toe boots too. These are the bulkiest pair of boots I own and while this type of shape might not flatter shorter, skinnier gents, I think it works well for this particularly look, plus it gives me a good two inches in height.

• Puffer vest = casual
• Heavy button up = casual
• Henley shirt = casual
• Dark wash jeans = smart/casual
• Moc toe boots = casual
• Fingerless gloves = casual

I finish the look by layering a puffy vest over top and chunky, woolen, fingerless gloves to add to the ruggedness.

Look #11: The Refined Blazer

I love a tweed blazer. It’s the ultimate smart casual jacket.

It has texture and weight to it and pairs well with an oxford cloth button down (OCBD) and light sweater. This is a classic smart casual move layering a OCBD under a lightweight sweater.

• Tweed blazer = smart/casual
• Crew neck sweater and OCBD = smart/casual
• Woolen trousers = smart
• Cap toe boots = smart/casual
• Pocket square and lapel pin = smart
• Scarf, gloves & ear warmers = smart (functional pieces)

I’m wearing wool trousers yet again and a pair of brown cap toe boots. Depending on the weather, you can throw on a chunky woolen scarf, gloves and ear warmers to keep you warm and looking stylish.

Look #12: The Rolled & Layered

This look features the ever versatile and trendy rollneck sweater, one of my winter staples. I pair the turtleneck with woolen trousers and sleek suede navy cap-toe boots for an elegant aesthetic.

I threw on a woolen shawl collar cardigan with a fair isle, cream colored pattern to add some visual interest to the look. Keep in mind the proportion of the pattern is relatively small and so appropriate for a modest man.

This is a style that looks great with a topcoat and gloves. It’s a dressy look, but still casual because of the rollneck and cardigan.

• Topcoat = smart
• Turtleneck & cardigan = smart/casual
• Woolen trousers = smart
• Navy suede cap toe boots = smart/casual
• Gloves & ear warmers = smart (functional)

Something like this would make for a perfect winter uniform.

Look #13: The Winter Way

For this final look there’s quite a few elements at play here.

I kept it going with the patterns and so I’ve paired this tribal patterned sweater with gray slim corduroy pants. I layered the sweater over top of a white OCBD. And then down low I’m wearing the versatile suede chelseas yet again.

Finally for a top layer I thought a down parka would set the look off perfectly.

• Down parka = casual
• Sweater & OCBD = smart/casual
• Slim corduroy pants = smart/casual
• Suede chelsea boots = smart/casual

You’d think the parka is ultra casual, which it is pretty casual but a smart OCBD and a tailored aesthetic along with sleek chelseas makes for perfect winter smart casual look and one of my favorite out of all the looks.

In The End

I like to think of smart casual style as a form of dressing well. It’s an often confused and underrated dress code. But I hope that this article helped to demonstrate how you can pull off the smart casual aesthetic.

Before we go, I mentioned tailoring quite a few times in this article. And as you may know, it’s mighty difficult for modest men to find well tailored clothing off the rack and so it’s important to find a good tailor and establish some sort of relationship with him/her.

No matter what, remember that personal style is self expression and there’s no wrong way to go about it. It’s all about wearing what you love and what makes you feel good. Style is a journey, and in the end, have some fun with it.

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Questions about smart casual style? Leave them in the comment below!