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Dressing Casual Is The Secret To Effortless Style; Here’s All The Right Ways To Do It

If you want to be stylish, buy the latest trending threads. If you want to remain stylish then just keep it simple. Today we’re addressing the latter in a little game we like to call casual wear. Okay, it’s not so little.

In fact it’s often a massive question mark amongst many in the men’s style space. What is casual wear? When can you wear it? Are jeans casual wear? All valid questions which we’re about to tackle head-on in the comprehensive guide.

By the end, we guarantee you’ll be the king of casual clothes for men.

In This Story…

What Is Casual Attire For Men
When Is It Appropriate To Wear Casual Clothing For Men
When Not To Wear Casual Clothing
What To Wear On Top
What To Wear On The Bottom
Best Casual Shoes
Best Casual Accessories
Casual Go-To Looks

What Is Casual Attire For Men

The dress term ‘casual’ clothing for men is one of the most wildly overused words in the modern sartorial lexicon. For the uninitiated, it can run the full gamut of a Bintang and boardies to a sports coat and chinos. However, for the purposes of the modern-day gent, ‘casual attire’, more than anything else, should speak to an informal yet elegant mode of dressing. Not so much a dress code as an attitude and approach to personal style, casual attire is a true art that, once mastered, should be able to hold you in good stead for most occasions. Here, we explain how.

When Is It Appropriate To Wear Casual Clothing For Men

The average chap spends most of his life in casual outfits. They’re the run about outfits you wear when grabbing a coffee; heading to sporting events; meeting mates for a drink and everything in between. In short; the garb you wear for the routine stuff in your life. However, just because it’s quotidian doesn’t mean it should be treated with any less care or nuance than ensembles for more formal events.

The very nature of casual attire is that it’s adaptable. A pair of chinos, chambray shirt and some classic sneakers should be able to carry you from Sunday morning brunch to an afternoon at the pub and beyond. And that’s why casual should not be misinterpreted as an excuse to be slovenly. Not to be mistaken for athleisure or beachwear, casual attire is understated yet stylish. It’s a pair of slim-fit jeans with a well-cut t-shirt, it’s a denim jacket paired with chinos and Chelsea boots. In short – and as a rule – if you wouldn’t feel comfortable wearing it to an informal restaurant for dinner, it’s probably not casual.

When Not To Wear Casual Clothing

There are some who take inexplicable delight in flaunting the dictums of a dress code. I am not that person, and nor should be any discerning gentleman.

When it comes to when not to wear casual attire, the rules are simple; it’s simply when the dress code states otherwise. And sometimes a dress code isn’t stated – it’s simply implied via the nature of the event. For example, a cocktail party naturally calls for a lounge suit or smart blazer and trousers. In a similar vein, opening night of a play or even a gallery opening suggests a more elevated, formal code of dress.

This isn’t just a nod to convention either. To not meet the dress code signifies a lack of care and manners – not only to other guests but most importantly, to your hosts. Dressing to the attire standards is a nod of respect and an easy way to distinguish yourself as a true gentleman.

What To Wear On Top

If you’re starting to build your casual clothes wardrobe, the first thing to focus on is some classic button-down shirts. Experiment with different brands to find a fit that suits you and then invest in a few classic colours and prints. What’s fantastic about this style is that it can be dressed up or dressed down throughout the day.

If preppy isn’t your thing, look at a slightly more rock-n-roll (but no less cool) denim shirt. Invest in a deep indigo version and a lighter wash and pair with pale coloured trousers in either white or taupe.

In the cooler months, look to layer over a shirt with a fine-knit, crew neck sweater. Navy is a go-to and looks equally sharp over a collared shirt as it does with a plain white tee. Once you’ve got some core colours covered off, sweaters can also be a great opportunity to experiment further with colour and texture. Uniqlo releases a range of fresh colours each season that can add some flare to your standard casual get-up. However, if you’re looking for something even more avant-garde, look to the likes of Reiss or Hugo Boss. You’ll find chunkier styles in bolder colours that are perfect for when the mercury drops.

To top off your outfit, round it out with a classic denim jacket in a dark indigo wash. Nudie Jeans has a great selection that leans more into urban cool than it does tired rocker. Alternatively, a quilted gilet is another excellent finishing touch. Try Brooks Brothers or Suitsupply for styles that give a nod to the British landed gentry and that’ll look just as at home in the countryside as they will in the big smoke.

What To Wear On The Bottom

Nothing says casual like jeans. And whether you favour a light wash or an inky, dark one, they’re a staple that numerous looks can be based around time and time again. When it comes to styling jeans, roll up the cuff to show some of the selvedge (the inside seam) and don’t be afraid to elevate them with a button down shirt or even a light sports coat.
The key thing with jeans when being worn casually is to steer clear of too much detailing. The motor-cross piping and the excess rips might seem cool but they ultimately detract from an otherwise chic and perfectly good ensemble.

When looking to up the ante on your casual look, you can’t go past a pair of classic chinos. Opt for a pair in a slim fit and seek out neutral base colours like olive, navy, white and beige. These pair excellently with either a tee or a button-down shirt and will comfortably take you from the pub to a mid-week dinner. Pair with some classic sneakers and a shawl neck sweater and you’re set to go.

In the warmer months, it’s perfectly permissible to wear shorts as casual attire. However, they can’t just be any old pair of boardies. Instead, look for tailored Bermuda shorts in cotton twill or seersucker. Top them off with a linen shirt, a canvas belt and some suede loafers or espadrilles for a look that screams summer style.

Best Casual Shoes

When it comes to casual footwear, it’s hard to beat a loafer. Whether you’re a fan of the penny style, tasselled or horse-bit, these shoes pair effortlessly with jeans, chinos or even tailored shorts and add a level of polish to casual attire that won’t go unnoticed.

In the warmer months, play with suede and canvas constructions that add a touch of texture. Also be open to experimenting with bold colours like azure, burnt orange or even yellow. This unexpected flourish gives personality and amps up the fun – just be sure to Scotchgard them first.

When looking at options, G.H. Bass & Co. has a terrific selection in more traditional leathers and suedes as does Meermin Mallorca. If you’re bold enough to foray into more zesty styles, try the likes of Santoni or even Aquila who often releases a statement colour or two each season.

Of course, loafers aren’t the only option when it comes to casual attire and it would be remiss not to include the classic sneaker here. A fresh white sneaker is indeed the epitome of relaxed style and works with most styles of trousers and shorts. However, the key is keeping them clean. Nothing looks worse than a sharp ensemble matched with a pair of grubby plimsolls.

When it comes to finding the perfect pair, it pays to shop around for a style that marries comfort with elegance. Personal favourites include Common Projects, Vejas and Stan Smiths.

Best Casual Accessories

Accessorising a casual outfit is all about details. Whether it be your belt, sunglasses or watch, these final touches are an opportunity to inject some personality and panache to your outfit. First let’s start with the easy stuff – belts.

There is one strict rule with belts and that is to always think about them in relation to the shoes that you’re wearing. For example, if I’m wearing sneakers and a pair of chinos, I’ll generally opt for a more relaxed canvas or suede belt in navy or grey. Alternatively, if I’m wearing a pair of oxblood, polished loafers, I’d look at pairing with a similarly dark brown-ish coloured belt. This isn’t to say that they need to match exactly, rather it’s that they need to have a relation to one another.

In regard to sunglasses, it’s worth investing in a classic pair. Beyond giving a nod to timeless style, a classic set of sunnies can quickly become a personal statement. Whether you go for a pair of Ray-Ban Clubmaster, Dior SoReals or even Persols, they’ll add effortless cool to your outfit.

Jewellery isn’t for every man and it can feel a touch gauche if you’re not used to it. However, if you’re one to dabble, it’s worth looking for options that can become classics. Pieces like a gold chain from Cartier or a signet ring that’s been passed down through generations are simple touches that act as an extension of your personal style.

Casual Go-To Looks

You can’t have a guide without the right looks. From summer right through to winter, these are coolest casual wear looks you can steal today.

Linen Shirt With Fitted Pants

Light and breezy, the white linen shirt is a must-have when it comes to keeping smart and comfortable in the warmer-months. This shirt is designed to look relaxed – oozing effortlessness via an open-neck and the neatly rolled sleeves. The hem should be styled in a nonchalant half-tuck into pants at the front and without a belt.

Try teaming your white shirt with smart pants in a lightweight fabric and roll the cuff to expose the ankles. Add woven leather loafers, espadrilles or sandals (all no socks) for footwear that embodies summer nights. If you’re fully committed to the look, you can even buy your cotton pants pre-cropped, and do away with the hassle of rolling the hem. There’s something summery about short-length trousers (just like white linen shirts), so embrace it. You’ll soon be feeling like you’re on holiday in Europe, without leaving the comfort of Bondi, Byron or Burleigh.

Floral Shirt With Chinos

Floral prints offer more muted and mild in colour, letting florals venture into Autumn as well as Spring. However, there’s nothing heavily Hawaiian about floral shirts. These prints are more like abstract works of art; desert coloured and grubby-ed so the flowers could be seen as blotches or blurred colour until up close.

For the gardenia gent, fronds and ferns still abound but in subtle monochrome, appearing more textural and grainy than bold and patterned. For styling, juxtapose a button down floral shirt – in short sleeve or rolled – with heavy cotton chinos (lighter cheap chinos can also work during warmer seasons). Wear with penny loafers or monk straps in tan or brown.

Shirt Jacket With Jeans

Also known as the ‘shacket’, the shirt jacket – a hybrid men’s fashion item that combines the layering capabilities and sturdiness of the jacket with the design and lightness of a collared shirt – is taking men’s style further into fashion-cum-functional territory. And we aren’t complaining.

The perfect choice for when it’s Spring or Autumn, designers are making ‘shackets’ – in sporty nylons or breezy cottons – that work for every taste. To get the most out of it, wear the shacket closed (to the neck or slightly open) or layered over a basic t-shirt. The shirtjacket embodies the deconstructed elements of a casual blazer without the formalities of suit jacket, made all the more weekend-smart paired with your favourite tapered jeans.

Polo Shirt With Trousers

Polo shirts are experiencing a resurgence of late. No longer reserved for preppy jocks and pop-collared pimps, this season’s styles speak to a seventies revival (yes, designers are still loving the disco decade). Made from either lightweight cotton or piqué, they lend any outfit an element of authentic René Lacoste-cool.

Despite its aesthetic ties to the humble tee, a polo collar gives Summer pants a smart-casual finish, especially in the new season’s cuffed, army construction. Update this classic shirt with a change in textures, intarsia prints and an injection of colour, especially muted yellows, greens and blues. Worn solo, only button up the third button; never go all the way to the top.

Leather Jacket With Jeans

Nothing says casual weekend attire like a well-loved leather jacket flung over a fitted tee-shirt with a pair of jeans. However, buying a leather jacket can feel like a big investment – particularly if you’re looking at higher-end styles – so why not take a trial run with a classic style from the likes of ASOS or The Iconic first? A biker style is one that you’ll be able to wear time and time again, just remember that leather has natural give and it will stretch over the course of the first few wears.

When styling a leather jacket, adopt a less is more approach. Think basics with a good quality white tee-shirt from somewhere like Bassike and dark wash jeans. This looks sensational with a pair of fresh white kicks and no socks.

There you have it, the no fuss guide to casual clothes for men.

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It’s Going To Hurt — But That’s Not Necessarily A Bad Thing

As trainer Calliet told an exhausted Hudspeth: “This sh*t hurts — it’s supposed to — and we’re going to do it all over again.”

If you don’t have your own PT to tell you this at the end of a tough set, repeat Calliet’s next mantra in your head, “If you can be consistent throughout the whole process your body will start changing.”

Or, if that doesn’t work, console yourself with the fact that you’re not alone — Hudspeth felt the pain too.

“I feel like I’m just getting killed right now.”

The Diet Plan Is Brutal — But Effective

If you watch the video (at the bottom) you’ll see Hudspeth admit that meal preparation is the most difficult part of the process (for him), with the amount of time the average 9-5 worker has to trim chicken and roast sprouts being severely limited by the demands of life…

“For a person with a nine-to-five who is not an actor with a chef and not being paid to dedicate your life to this, it’s certainly more challenging.”

“What people don’t understand,” Calliet says, is that you can eat what you like and still learn to box, but to get the look that you want, “The real transformation comes with diet.”

“High protein, carbs when you need it, 1.5 to 2 gallons of water a day.”

A Gallon Of Water A day = Living In A Bathroom

“One thing I was not prepared for was how exhausting the gallon of water thing is.”

You Will Get Drunken Junk Food Cravings — But That’s Not Necessarily A Bad Thing Either

When Hudspeth fell prey to some Taco Bell cravings midway through the challenge (after sinking a few vodkas at a concert) he took it as a good sign, in his words, “Because I normally have no desire to do anything on a Saturday night.”

You Will Need To Be Consistent To Get The Desired Result

On the final day, Hudspeth came to the conclusion that, movie star or not, “If you take the time and consistency” you’ll get the same type of body as Michael B. Jordan (although perhaps not as substantially ripped).

Keep it up for a year though and The Rock’s the limit…

Your Self Worth Depends On Your Significant Other

As Shannon points out, if you find yourself depending on your partner for your self-worth, going poly could help you learn to walk without this crutch.

“For the longest time, I lived for verbal affirmation from my partners. In fact, it used to dictate how I felt within the relationship and even how I felt about myself. So it wasn’t exactly healthy.”

You Have A History Of Staying In Relationships That Weren’t Good For You

“Looking over the trends in my past relationships, I can (now) see where I ran into problems with unhealthy expectations,” Shannon says. “I got carried away with wanting to know the people I cared about also cared for me too.”

You Are An Idealist

“I love love. I love the idea of love. I have always wanted to love and be loved. So much so that I’ve prioritized it even when I shouldn’t.” While there is definitely something to be said for being an optimist, taking a walk on the ‘wild side’ could help you on your journey to self-actualisation, so that if and when you find someone you want to be completely exclusive with, you are more ready for it.

You Think Polyamory Is Just A Way For Douchebags To Justify Their Behaviour

As Shannon recalls, the most offputting factor about polyamory “was how many men I’ve met who call themselves poly but only treat their primary partner well — if even.”

However, even though “there are way too many entitled ‘poly’ men treating partners like objects and gap-fillers,” that doesn’t mean the whole concept is flawed and there aren’t people out there doing it the right way.

You Always Need To Be In Control

“Falling in love with a polyamorous man helped me become chill AF.”

Of course, any man or woman is liable to make casual dating mistakes, but becoming polyamorous might help you relax about the little things a little more — or at least force you to work on your communication skills.

“Maybe it’s not specifically because Mister Atlanta is poly. But his poly nature forced me to deal with some of my relationship issues and move forward.”

The conclusion? It may not be for you. It may not even be for you to try. But if you are interested in dipping a toe into the polyamorous dating scene then you could learn more about yourself than you realise.

The rise of toiletry bags

Whether you call it a toiletry bag, a shaving kit or a Dopp kit, these small bags dedicated to your manly possessions have begun to catch on in recent years thanks to the downsizing of electronic devices and slimming down of wallets. This movement has all but relinquished the need for cumbersome messenger bags when something like a man clutch with a built-in handle will suffice. It’s also the same reason why things like fanny packs are also popular with guys these days.

What to put in toiletry bags

Tradition dictates that toiletry bags are a man’s central location for grooming essentials like shavers, creams, moisturisers, hair products, toothbrushes and any other essentials you may use to polish up abroad. These days men are foregoing that definition and throwing in their non-essential grooming items like keys, phones and wallets instead. The choice is essentially yours, but we suggest you don’t mix the two categories unless you want hair gel in your wallet.

Features of the best toiletry bags

They might not be seen as much as a regular bag but make no mistake there’s an art in picking the right one. Our advice is to always choose lean, durable and compact toiletry bags. Given they’re going to accompany you on your greatest adventures, it’s important to buy quality toiletry bags wherever possible. That’s not to say the cheaper ones need to be ruled out. If they look good and you’re just using them as a casual day Dopp kit to get around town, the non-leather fabric or polyester ones are just fine. If you intend to make them a part of your outfit, go for the higher-end ones which present as well as they function.

Speaking of function, look for toiletry bags with internal compartments which makes finding your possessions easier. The last thing you’ll want is your keyring grinding up against your $1,000 phone. Also, pay attention to the zipper quality. If it isn’t smooth and feels cheap then forgo it. A broken toiletry bag is the last thing you need to worry about when travelling.