30 Cool Casual Outfits Every Man Will Look Good In

Thousands of miles of column inches have been dedicated to men’s trends and fashion, but the simple fact is that most guys just want to look good without having to think about it too much. Time and mental energy are precious and so nobody wants to be fretting over how to look good day in, day out – especially when it comes to casual looks.

Trends are great for brands – they mean newness, and newness means more reasons to buy new clothes, but most of us have the rudiments of a great wardrobe already, we just need a few seasonal upgrades to keep everything looking fresh.

What the brands won’t tell you is that looking good is quite formulaic, and once you’ve settled on your aesthetic identity, you’ll be able to cobble together great outfits without even the slightest bit of head-scratching.

Below, our experts have compiled 30 casual looks that any man can achieve with ease. Most of the garments you’ll see below will likely already be stocked in your wardrobe. But if not, a few strategic purchases will allow you to create a tonne more looks.

The plaid overshirt

Every man should own a plaid overshirt. They are just indispensable. They bring color, pattern and texture in most cases, and can be thrown over a simple tee to instantly create an interesting look with an elevated workwear appeal.

Straight-cut navy pants look great with a red shirt, particularly when there is a hint of navy in the check pattern, as proven here. Finish with a pair of retro running sneakers and you have a comfortable casual fit that you can call on time and time again.

Black and olive

This color combination never fails. A black top or shirt with olive green pants – whether they’re tailored or baggy cargos – just work. There’s a military/utilitarian appeal to them that works best with loose silhouettes.

Since they’re both understated tones, they’re a great canvas to pop some bold-colored or chunky sneakers off.

Bomber squad

As above, the white tee and jeans combination continue to do the timeless style tango in this outfit, but an altogether more rugged aesthetic is created by the addition of the leather bomber.

The bomber jacket can always be relied upon to create a masculine silhouette, while the fact it’s leather only serves to amplify this. The black leather boots cement the rebellious edge this look oozes without appearing too try-hard. 

Casual overcoat

If there’s one statement coat you need in your wardrobe, it’s the camel wool overcoat. This menswear classic, while smart, can turn its hand to just about any casual look, including streetwear fits.

Combine it with a hoodie, track pants or wide-leg trousers, and a simple tee. It adds a layer of elegance and textural interest no matter what you’re wearing underneath.

Black on black

If the modus operandi of great casualwear is making it simple to do, then opting for monochrome looks should be first on your agenda. All-black outfits are easy to assemble, look invariably chic, and don’t require a great outlay on new items.

Mix up the fabrics and play with your silhouettes – you’ll get so much mileage from sticking to dark tones, too.

Bring the outdoors in

Fleece zip-throughs have become one of the most versatile casual pieces in the modern man’s wardrobe of late, simply because of the fantastic textural qualities they bring.

Sure, they boast a masculine utilitarian silhouette, but that dense fleece pile will elevate any casual look, not to mention keep you warm.

Throw them on over slick city pieces – like the drawstring black pants, crisp white tee and minimalist sneakers shown here – to create a juxtaposition that looks contemporary and considered.

The measure of athleisure

Often, athleisure naturally veers towards baggy silhouettes, but opting for a more fitted aesthetic will help make the look that little bit more refined.

This tonal grey and white combination sees a fitted sports hoodie teamed with streamlined shorts for a more svelte and innately smart approach to dressing down. A great everyday summer look.

Minimalist casual

Keeping things simple is the key to a great casual wardrobe, and that couldn’t be more true for your color palette. Stick to neutral and muted tones and let the textures do all the talking.

This two-tone look layers black on black, with a statement flight jacket repping a shearling collar, paired with khaki green wide-leg chinos and black loafers. The silhouette is relaxed, but there’s a refinement about the constituent parts.

Note: the peek of white tee is no mistake – it nicely frames the dark hues and creates separation.

Black & white

With hints of ‘skater chic’, combining a pair of black jeans (whatever the wash) and a white T-shirt is an easy and effective approach to casual dressing that feels young, urban and slightly edgy. This is especially true if you play with your proportions, as shown here: the tee is slouchy and oversized, while the jeans have a narrow taper down to the ankle.

It’s a versatile canvas that you can tweak here and there to create completely different looks: add statement sneakers, or a pair of combat boots, for example. Your layering options are endless, too.

Tri-color classicism

Clean lines and great fabrics are the hallmarks of sophisticated casual looks, as this ensemble demonstrates. What is a very simple blue jeans and white T-shirt pairing is instantly upgraded with the addition of the tan suede bomber, which gives the outfit much more depth thanks to the texture.

The white minimalist sneakers keep the look super fresh too. Three understated colors working together in harmonious style.

Half-zips and quarter-zips

It wasn’t all that long ago that half- and quarter-zip jersey tops were menswear relics, but with the popularity of modern preppy, these handy layers are back, forming a comfortable and stylish addition to your casual wardrobe.

They can be worn with light-wash jeans and running sneakers for an on-trend ‘dad’ vibe, as shown here, or can be layered over an OCBD and tapered chinos for a more classic preppy outfit.

Casual leather jacket

Another monochrome go-to that never gets tired is the black jeans/T-shirt/leather jacket trifecta. In this case, the jacket is a nice rendition of the classic Perfecto biker jacket, originally created by Schott, but you could just as easily wear a minimalist Café Racer.

It’s an edgy, masculine and super-simple casual outfit to put together. Plus a leather jacket is timeless and only gets better with age.

Textured outer layers

Keep your silhouette classic and your color palette restrained and you’ll no doubt create some good looks. But to concoct great looks, you’ll need to introduce some texture.

Materials such as wool, suede, leather or even technical fabrics give your look some depth, which is especially important when it comes to short jackets since you have less surface area to make an impact.

This outfit is a case in point, with the napped wool bringing a sense of character and richness of color to an otherwise bog-standard navy/green overshirt. Note how the green pants pick out the base color of the shirt. The finer details matter, gentlemen.

Button-down and jeans

Here’s a super-simple casual look that you probably already have the elements hanging in your wardrobe.

A navy Oxford shirt and jeans combination marries blue tones with the texture of denim, and can be neatly bookended with some contrast white sneakers for an effortless casual look.

You could also tweak this fit by wearing a white tee underneath and leaving the shirt open.

The suede jacket

Once again, we see black and olive come together effortlessly, only this time the heavy lifting is not done by the tone but by the texture: suede.

A suede jacket is a fantastic piece of style weaponry to have in your arsenal as it never fails to look both masculine and reassuringly expensive.

The natural texture of the fabric will provide your casual looks with depth and contrast, which is especially important if you only wear dark colors.

The long-sleeve T-shirt

If there was one garment that most men don’t own enough of, it’s high-quality long-sleeve T-shirts. Having a rotation of heavyweight cotton long-sleeve tees in your wardrobe is a game-changer for styling looks.

Whether in white, black, off-white, navy or shades of grey, these no-fuss crewnecks are brilliantly versatile layers that can look both smart and casual whenever you call upon them.

Keep it straight

Whether they’re jeans or cotton twill, casual straight-leg pants with a roomy silhouette have been on-trend for a few seasons now and look set to become a mainstay of modern wardrobes thanks to their versatility.

Light-tone styles like these are great for creating relaxed tonal looks, whether you opt for a sporty hoodie or a more preppy aesthetic.

Overshirt Excellence

Speaking of overshirts, having a variety of white and off-white styles hanging in your wardrobe is a shrewd move.

From casual brushed cotton OCBDs to grandad collar styles, white shirts bring a sophisticated element of contrast and go with anything.

Khaki pants and a contrast tee (here it’s black) are all you need for the white overshirt to do its thing.

James Dean casual

Of the most iconic menswear looks in history, there are none more simple to execute – or more effective – than the white tee and jeans. If it worked for James Dean and Marlon Brando, it will work for you. The combination is masculine and effortless.

What we really like here is the raw denim selvage jeans, and the addition of the chunky shawl collar cardigan (a Steve McQueen favorite), both of which add an element of elevated texture.

Blue and green should be seen

Monochrome looks are for everyone, so if you’re the kind of guy who wants a greater diversity of color in his wardrobe, try experimenting with combining blue and green.

They make for excellent dance partners, especially the more understated tones, which are naturally complementary, as evidenced in this look.

Keep On Truckin’

On the subject of blue and green, this look only reinforces what we said about the effortless way these two colors combine. The highlight of this particular ensemble is the denim jacket, a hero of Americana and a timeless garment loaded with inherent masculinity.

It’s versatile too, since you can just as easily throw it over a hoodie as you can a shirt, tee or crew-neck sweater.

Buy the best quality you can afford, preferably in raw denim, and enjoy breaking it in. You’ll have a friend for life.

The denim trucker pt. 2

So good we had to include it twice. This time around, the denim jacket has been paired with navy tapered chinos for a tonal blue look that looks good on any man.

The hint of grey Henley shirt underneath the jacket creates a nice contrast, while the suede boots bookend the outfit with some texture.

The denim shirt

We’ve covered the timeless style of the denim trucker jacket, but the denim shirt is another essential casualwear piece to have in your wardrobe.

As in this look, we like it best as an overshirt style, layered open over a crisp white T-shirt or sweat. The shirt has just the right amount of ruggedness to it, thanks to the twin breast pockets and denim’s unique textural qualities.

This vibe is then mirrored on the bottom half by the navy tailored cargo pants, which feature slim flap pockets to the side.

Tonal navy

Here’s an example of a total navy outfit that is extremely well executed. The key element here, and what your eye is naturally drawn to, is the high-quality selvage denim jeans with a substantial turn-up. Not only does this little styling touch show off the selvage edge (a signifier of quality for those in the know) but it also extra space for the boots to shine.

The hoodie and the coat meanwhile create a modern silhouette, with the former reinforcing the look’s casual credentials.

Overshirt and shorts

A lot of men struggle with styling shorts effectively, and it’s often because they don’t think about layering their top half.

Pairing shorts with only a tee or polo can expose your figure – and let’s face it, most of us don’t have movie star physiques – but incorporating an overshirt gives you that extra layer of interest and confidence.

Throw on some cool sunglasses and a pair of clean leather sneakers and you’re good to go this summer.

The T-shirt tuck

Classic khaki twill chinos are a casual wardrobe must-own. They are so versatile and can be worn with a wide variety of footwear, from rugged boots to smart minimalist sneakers.

As always, a crisp white tee perfectly contrasts against darker hues, while creating a blank canvas from which you could layer an overshirt, denim jacket, suede blouson or cardigan over for an elegantly relaxed aesthetic.

We like the understated simplicity of this outfit though, with the T-shirt tuck smartening up the aesthetic slightly.

Mixing up genres

A slightly more complicated way of dressing casually, but one that has bonus points for originality, is mixing up menswear genres. This look is built using tailored pants, running sneakers and a workwear-inspired overshirt – three seemingly clashing dress codes.

The secret to what makes it work, and not clash, is that each of the separate elements is pared back and simple – there are no patterns, no wild colors, just great textures and classic silhouettes.

Revert to the white shirt

If you’re ever short on ideas, the humble white shirt will always have your back. In this case, it comes to the rescue by making what looks to be a fairly average pair of jeans punch well above their weight.

Opt for white shirts in cotton fabrics with a bit of texture to them to avoid looking like you’ve just thrown on your 9-5 number.

Denim and suede

Denim jeans with a suede jacket is a marriage made in heaven. And when combined with a plain white T-shirt, this is a look that never gets old.

Both the suede jacket and selvage jeans will give you that luxury veneer, while you can use your choice of footwear to angle the look how you wish – leather Chelsea boots for a classic vibe, or statement sneakers for a more contemporary fit.