Your Guide to Casual Dressing

by Jamie
Stenströms - Official Website - Swedish Shirtmaker since 1899

Reaching inside your wardrobe without a clue of what to put on? This is your guide to casual dressing from what to wear on the streets to how style business casual for the office.


When you’re away from your desk during the week the clothing you put on your back is more than likely going to be casual. However, that doesn’t mean you have to lose all sense of style – enter our easy to follow guide on men’s casual clothing.

What is Casual Dress?

Men’s casual wear translates to style with comfort. These are clothes that won’t cause too much of a stir for trendsetters but are ideal for those everyday trips where durability and fit are key. Casual dressing embodies a sense of streetwear with fashion; therefore casual clothes for men tend to lean towards the absolute wardrobe basics.

The trick to how to dress casual is to choose pieces that aren’t specific to any given season, and are made from a quality material and cut. Casual dressing calls on layering separates – be it a pair of well-worn jeans with a basic T-shirt or an Oxford shirt tucked into an easy pair of summer chinos. It depends on the occasion that you’re dressing for. A casual outfit to run errands will differ from a casual outfit for a summer party or event.

Casual Wear for Men

So you want to know how to dress casually well? These are the key items you should be investing in to achieve dressing casual.

A basic crewneck t-shirt may be an obvious choice, but it’s an item that will practically go with everything in your wardrobe. A casual cotton T-shirt in easy to wear shades of white, grey and black, will carry you throughout every season and can be layered beneath thicker knit jumpers, smart blazers, full-length coats and styled with any pair of trousers – the possibilities are endless


A good pair of jeans should fit you well and be comfortable to wear. The type of denim wash is all down to personal preference, but be sure to avoid styles that are overly ripped, frayed or feature any exuberant design details. A slim fit jean will suit most body types and can be coordinated with everything from a T-shirt, hoodie jacket to a tailored blazer.


The hoodie came into fashion during the 1930s as a layering alternative for manual workers. Fast-forward a few decades and it has become the item of choice for street style aficionados and athletes alike. French brand Vetements is making waves with their street-inspired pieces, with the hooded jacket being a key piece in their collections.


The trainer’s strength in performance and endurance makes it the ideal shoe for those looking to dress down. Wearing trainers with almost anything has become popular with the street style crowd. A minimalist’s wardrobe will suit pristine white trainers or a shoe with a graphic black and white design. Meanwhile, a more urban, street-lead guy would opt for a trainer design with sportier materials such as mesh and leather.

Casual Knitwear

Knitwear should be roomy enough to allow for optional outfit layering, but also snugly fit to avoid any oversized outfit fails. A casual knit jumper made from merino wool, cashmere or lambswool is the perfect option for those of you who don’t want to don a jacket. A V-neck silhouette is typically worn on more formal occasions, while both can be worn on summer evenings and during the transitional period between autumn and winter.

Casual Jackets

Designs like the bomber jacket, denim jacket and leather jacket call on a try-before-you-buy mantra. That means that if you want a stylish fit then go down a size. There’s nothing worse than a loose fitting jacket, even if the look you’re going for is the men’s casual style.

A good leather jacket will set you back, but after a few years of wearing it, the leather will practically mould to your body. For more seasonal pieces like the bomber and denim jacket, you can be a little more daring in your style choices. Style them with a basic T-shirt and jeans, or layering a hoodie beneath.

Summer Casual Outfits

There have been multiple famous gents sporting the casual look this summer. Draw inspiration from their style choices and implement a few tips and tricks into your casual dress.

Oliver Cheshire

This Brit-born model may have good looks to envy but his casual style is pretty easy to achieve. Oliver Cheshire is most likely seen out and about in town donning a smart three-piece suit, but on his off days, his casual dress combines street with style.

A basic grey slub tracksuit is the ultimate comfort outfit to don on the streets. Cheshire has paired it with a smart double-breasted pea coat to elevate the look from workout to fashion week appropriate.

Tinie Tempah

Adding some street smart inspiration is rapper and London Fashion Week Men’s aficionado Tinie Tempah. Tempah is known for his daring fashion choices and his ability to mix highstreet with designer labels to achieve an individual look.

Business Casual Dress for Men

Casual dressing is all well and good, but what about when you want to translate that look for the office? Sometimes a classic two-piece suit just won’t do, and when the hot summer months hit alternating your usual uniform for something more seasonally appropriate is of the utmost importance.

Save the tuxedo for extra special events and instead look to adding a casual suit jacket to your collection. In most cases (and in particular during the summer) a light linen blazer is the go-to. Linen allows for breathability and is an ideal material for summer parties. A one-button enclosure jacket is the most casual silhouette you can find on the market, but also look for jackets that are unfussy in their design – differentiating formal tailoring from casual tailoring.

Chinos Instead of Trousers

Casual fashion is encapsulated in a pair of well fitting summer chinos. As an alternative to a classic pair of suit trousers the summer chino comes in a variety of colours, but to achieve that laidback style opt for neutral shades like tan or white rather than primary colours. Chinos can be paired with trainers and dressier shoes. Style with a matching jacket or a shirt tucked casually in with a leather belt. You can amp up the street vibe of the chino trouser by throwing on a hoodie and pair of high tops.

Office Appropriate Accessories

Consider changing up a casual outfit with some office-appropriate accessories courtesy of a summer hat and a pair of sunglasses. A classic bowler hat comes reinterpreted for summer in breathable canvas and woven cotton and can be worn with a head-to-toe linen suit to achieve a dapper (yet casual) business look. Elsewhere a sturdy pair of sunglasses is a summer essential. Stick to retro inspired shapes like the aviator or wayfarer with a tortoiseshell or black outer and dark tinted lenses.

Men’s Casual Dress Shirts

A staple to any business casual look is the dress shirt. Consider the fit of the shirt above everything else. It should look snug without being too tight, and anything loose should be intentionally oversized. Differentiating a casual dress shirt from a smart suit shirt is the material used and the colour palette. For everyday dressing opt for a wearable granddad collar style or a shirt with a graphic print.

Oxford Shirt

Although an Oxford shirt may have full-length sleeves, a more casual approach to the classic style is to choose an Oxford shirt with a short sleeve. It’s all about adapting the wardrobe basics to achieve a casual aesthetic. That being said the Oxford shirt in whatever variation is one of the go-to shirt styles for those looking for an easy dress shirt. For the boardroom choose styles in light blue, pink and grey, and for evening events call on black and classic white styles to pair beneath a blazer.

Granddad Collar

Change up the style status quo with a modern denim granddad collar shirt during the summer months. Choosing this style in denim automatically makes for a casual look, and when paired with chinos and trainers, creates an easy day-to-day outfit. Because a granddad collar shirt has a slightly different silhouette the key is ensuring the fit isn’t too snug so as to allow for full button enclosure.

Polo Shirt

Coveted by golf players and tennis players alike, the classic polo shirt can be an easy casual alternative to a stuffy dress shirt. The benefits of a polo shirt are that its short sleeved and breathable. Choose a style in lightweight cotton knit, and experiment with patterns such as stripes, polka dots and of course block colours. Pair with chinos, jeans and summer shorts. This style works wonders with sandals and casual boat shoes.

Printed Shirt

If you aren’t afraid of injecting a little colour and pattern into your casual wardrobe then look to the printed shirt to gift you outfit individuality. Currently on trend this summer is the revere collar shirt – an open collar styled shirt with short sleeves. Prints can vary from floral to geometric. If you do opt for a printed shirt then keep the bottom half of your outfit slick and simple with either jeans or black cotton shorts.

Business Casual Outfits

Want some outfit inspiration to accompany your business casual dressing guide? Look to these dapper gentlemen and take note.

Ryan Gosling

Actor and stylish gent Ryan Gosling often changes up his style, experimenting with sharp tailoring and more casual street-inspired clothing, and sometimes combining both on the red carpet.

Kanye West

The ever-controversial rapper may sway opinions on social media but his off-duty style has inspired a nation of followers. Kanye West is the master of casual wear and often mixes sportswear with more high-end labels. Kanye is one of the pioneers of men’s casual fashion.

Your Guide To Casual Dressing

  • Basics are an absolute essential in your casual wardrobe. To define a casual look it’s all about interchanging pieces throughout the seasons without complication.
  • Statement pieces will elevate your casual wardrobe to ensure you stand out from the crowd for all the right reasons.
  • Business casual dressing shouldn’t just be restricted to tailoring as proven by the dapper gentlemen sporting business looks on the red carpets.
  • Shirts come in four main categories when considering a casual wardrobe: Oxford shirt, granddad collar, polo shirt and printed shirt.
  • Remember that casual dressing is all about combining street with fashion. You never want to be too far on either side.

On That Note

What have you learnt from our ultimate guide on casual guy’s fashion? To recap it’s about choosing classic pieces that will carry you throughout the season and that can pair with more statement pieces without fuss. Remember to consider the fit of everything you add to your casual wardrobe. If it’s oversized then it should be intentional – the same goes for snug shirts, especially if you want to button up all the way to the collar. Keep in mind a strict colour palette when you’re shopping and always choose pieces you’ll be comfortable in wearing.

Feature image from Pinterest

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