8 Casual Shirts Every Stylish Man Should Own

Image Credit: Luca Faloni

A good selection of casual shirts is the backbone of the well-dressed man’s capsule wardrobe. Properly stocked, it allows him to traverse the seasons in style, navigate all manner of social settings and dress codes, and layer like a pro.

Casual shirts have come a long way over the years. They can be traced back as far as Ancient Egypt in their primitive forms, going on to become the undergarment of choice for the Western upper classes through the 17th, 18th and 19th centuries. As time progressed, shirts gained popularity as garments in their own right and during the 20th century it became common to wear one without a vest or jacket.

Since then, casual shirts have evolved into multiple subsets. There are countless variations out there to choose from, but are all of them worthy of a place on your shopping list? We’d argue not, but there are a few key casual shirt styles we firmly believe every man should own.

The Classic Oxford Shirt


If you’re going to buy just one casual shirt, best make it a classic Oxford-cloth button-down (or OCDB for short). Straddling the divide between smart and casual, this traditional cotton shirt is simple, timeless and goes with just about anything. It’s the king of casual shirts and something no self-respecting man should be without.

To ensure maximum versatility, go for a classic cut – not too slim, not to loose – and keep the colour subtle. White, pale blue and pastel pink are some of the most popular colours for OCDBs, mainly because they create a nice blank canvas and can be easily dressed up or down.

The Heavyweight Flannel Shirt

Billy Reid

When the mercury plummets, a thick flannel shirt is an excellent insulator and perfect for layering up. The brushed cotton fabric helps to lock in body heat and takes dye extremely well, resulting in rich colours. Because of this, flannel shirts have become a common vehicle for patterns, allowing you to give your outfits a subtle focal point and draw the eye.

A good winter flannel should be loose enough to layer over a T-shirt or even a sweatshirt. The fabric should be substantial, but not to the point that it feels bulky and restrictive when worn underneath a coat or jacket. Wear it with workwear pieces like leather boots and raw denim.

The Cuban Collar Shirt


Breezy and ready for fun, a Cuban collar shirt is the ultimate summer companion when it comes to casual shirting. The style features a spread collar, which reveals more of the chest than a classic collar, and eye-catching patterns are popular. That said, a plain Cuban collar shirt is a handy garment to own too, channelling all of the laid-back cool in a slightly more subtle manner.

Given their chilled-out, breezy nature, we think Cuban collar shirts are best not worn too tight. A slightly relaxed fit will allow your torso room to breathe in the heat and aid comfort and freedom of movement.

Dress it up with tailored pants and loafers, or down with swim shorts and a pair of sandals.

The Linen Shirt

Billy Reid

When it comes to summer, ‘smart’ tends to be a byword for ‘sweaty’. If you want to look sharp, you have to don a shirt, and thanks to the fact that most of them are made from relatively heavy cotton, it can be a battle trying to stay cool. That’s where a linen shirt comes in. It’s airy, quick drying and excellent at wicking moisture away from the skin. Because of this, we believe every man should have one in their summer shirting rotation.

A linen shirt should fit just like an OCDB: somewhere between slim and relaxed, with seams that sit on the shoulders and a hem that rests just above the hips.

Go for light colours to make the most of linen’s cooling properties, and pair it with drawstring pants and canvas sneakers for an effortless summer smart casual outfit.

The Band Collar Shirt


A band collar shirt does away with the classic pointed collar of more traditional shirts and instead incorporates a straight, stand-up collar. This gives this style of shirt a clean, modern look, making it a quick and easy way to give almost any smart casual outfit a contemporary twist.

Band collar shirts vary a lot from garment to garment but generally speaking it’s best to opt for a classic fit. This will allow for the greatest degree of versatility and works well with most body types. We’d suggest going for a plain white option to give yourself a modern alternative to a classic white OCBD.

The Chambray Shirt


This lightweight relative to the denim shirt retains all of its cousin’s texture and Americana appeal without any of the overheating. It’s a great option in warm weather, bringing a tactile element to both casual and smart casual looks. It’s perfect for layering during the cooler portion of the year too, and because the fabric is less cumbersome than denim, it’ll slot easily underneath an overshirt, jacket or coat.

A good chambray shirt will fit well in the shoulders and body, with enough room for a light layer underneath. Indigo is the traditional colour but there’s something to be said for grey and lighter shades of blue too.

Pairing with jeans can work well, for a modern take on double denim, but just make sure the shades aren’t too similar. In fact, they should be different enough to contrast with one another; light and dark.

The Polo Shirt

Luca Faloni

Sometimes a collared shirt is too smart and a T-shirt too sloppy. For such occasions, a polo shirt is your best friend. Whether it’s short-sleeved or long-sleeved, this lightweight layer can elevate up casual outfits and tone smart looks down. It’s a preppy clothing staple and something every man should have hanging in his wardrobe.

The fit of a polo shirt should be slim without being tight. The seams should sit on the shoulders and, if it’s short-sleeved, the sleeves should sit a few inches above the elbow. We’d suggest teaming one up with other preppy pieces like loafers, chinos, a cardigan or Harrington jacket to really embrace the Ivy League aesthetic.

The Knitted Polo Shirt

The Resort Co.

This woolly alternative to the classic polo is perfect for adding texture to outfits. It’s ideal for layering in the colder months and looks great in autumnal, 70s-inspired colours like burnt orange, mustard and chestnut brown.

It may be a casual shirt, but a knitted polo works surprisingly well with tailoring. Dress down a suit by switching a dress shirt for one, or go down the separates route and wear one with some drawstring pants and an unstructured blazer in contrasting colours.

Paddy Maddison

Paddy Maddison is Ape's Style Editor. His work has been published in Esquire, Men’s Health, ShortList, The Independent and more. An outerwear and sneaker fanatic, his finger is firmly on the pulse for the latest trends, while always maintaining an interest in classic style.