How to style a men’s dress shirt

From the formal suit to a relaxed brunch, the dress shirt is a deeply versatile item that should exist in anyone’s wardrobe.

Learning how to style this type of shirt will serve to level up your fashion game completely. In this short article, we’ll break down what a dress shirt is, the variations, the appropriate environments, the sizing/fitting, and importantly, the styling.

FYI, thanks to AI imagery software, we’re able to create very specific fashion and hairstyle examples to illustrate the points being made. In some cases, imagery is exaggerated to hammer home the point. Also, assume links that take you off the site are affiliate links such as links to Amazon. this means we may earn a commission if you buy something.

Why wear a dress shirt?

This is a bit of a weird one – depending where you look and who you ask, the dress shirt can be anything from a smoking shirt for a tux to any collared button-up. Any description of a dress shirt with the latter criteria would then tread into the weird territory of calling a flannel a dress shirt, or calling one of those silk button-ups with 2000s-era dragon designs on them a dress shirt (those shirts are cool but maybe not with a blazer).

For our purposes, I think it’s best to treat the dress shirt as a bit of a middle ground between the two with a bit of a lean toward the formal. The way I view a dress shirt is usually in a semi-formal context. That means appropriate in the typical corporate office setting, wearable with a suit (of any kind), and even able to be slightly dressed down depending on the context and accessories (dress shirt and shorts can work well – sometimes). In a British English context, the dress shirt is more closely attached to highly-formal evening wear, so used at a fancy gala or black tie event, worn with a tuxedo or sharp black suit. We’ll bend this definition slightly, allowing the dress shirt to be explored in the context of semi-formal (and even slightly casual) contexts, but still equally applicable to the highest level of formality. In order to figure out exactly what a dress shirt is, we need to establish what it is not.

What’s the difference between an Oxford shirt and a Dress shirt?

The Oxford shirt and the dress shirt are both important and versatile clothing pieces for the fashionable man. While the two types of shirts are relatively similar and can be used in similar contexts, they carry key differences that are worth knowing. You wouldn’t want to use an Oxford shirt under a formal suit, for example, but both can be interchangeable in a more casual context that doesn’t require a blazer. Having a firm grasp of their differences and unique features will allow you to maximize your style with both types of shirts in the appropriate context. Technically, given both garments have full-body buttons, a collar, and long sleeves, both can qualify as dress shirts – for the context we’re exploring however, we need to identify the key differences that will ensure you know when and where to wear each one.

The Oxford shirt is the main ‘middle ground’ of collared shirts between the formal dress shirt and the more casual/workwear oriented flannel. The name ‘Oxford’ comes from the type of cloth it uses, not the English city. This cloth was first popularized in Scotland fabric mills and is the standard for the garment today. Even within the Oxford umbrella there are more casual and formal types of Oxford shirts: the ‘Plain Oxford’ and the ‘Pinpoint Oxford’ are the more iconic ones we know and recognize, with thick, stiff structure and button-down collars. ‘Royal Oxford’, which you can guess given the name, is a more formal option and is made up of tighter weaves and finer yarn to get it closer to the dress shirt consistency.

The Oxford shirt’s true versatility is in how you wear it with pants. Given how stiff the garment is and how easily it holds its form, it can be the main structural component of your outfit. You don’t have to wear it with pressed dress pants: chinos and jeans are often paired well with a white or pastel coloured oxford shirt. In the very casual business look, the oxford shirt can be often seen worn with a sport coat/blazer and jeans. Interestingly, some of the key features of this garment, like the buttoned collar, emerges out of English polo culture to avoid the flaps obstructing their view while they played.

For one, the main difference between these types of shirts comes down to fabric and weave choice. The Oxford is often a more standard basketweave style of fabric. This structural and stitching choice gives the Oxford a bit of rigidity and thickness, which can help it look boxier and highlight the crisscross pattern of the weave. As such, the Oxford is significantly less formal than the dress shirt as it doesn’t play as well with other formal layers. It also isn’t always 100% cotton, so the wear resistance is a little lower, making it slightly more susceptible to damage from rips, bends, scuffs and more. It is also a bit harder to iron without turning into a solid block of fabric – wearing it without wrinkles is important but that can usually be achieved by  The thicker material gives it lots of versatility for casual contexts however: wearing an oxford fully unbuttoned with a graphic tee underneath is a totally viable look, just as much as wearing it with some slacks buttoned up – this versatility, offering a bit more of a put-together look as readily as the low-key fit, is one of the key strengths of the oxford..

The dress shirt, on the other hand, is often woven with varying patterns like herringbone. The shirt will usually be quite a bit thinner than its counterpart and the more complex weave design can offer textural uniqueness. Often, dress shirts will have a bit of a ‘sheen’ to them because of the weave type and its 100% cotton composition. It is often woven in a manner that is significantly thinner than the oxford, which may lead some to believe it is a more fragile garment. However, the inverse is usually true: a well-made cotton dress shirt with a more complex weave will often be stronger than the thicker, more rigid oxford. Furthermore, the dress shirt is usually a bit more breathable thanks to its weight, weave, and composition. The dress shirt often has a higher thread count, one of the main features that gives this garment its silky feel. For me, when I think of the dress shirt, I usually envision the soft texture that makes for an easy fit underneath a blazer or a vest. The Oxford doesn’t always do this for me.

The next main difference between the two garments is largely in the collar style. The oxford is almost always presented with buttoned collar flaps. This is fundamentally considered less formal than the dress shirt, likely because formal dress collars require a bit of attention and ironing for them to look ~perfect~. In this sense, I wouldn’t encourage wearing a buttoned collar for any formal setting – it tends to stick out a bit. Wearing a tie with an oxford shirt is still a possibility but it has its own share of things to look out for – for one, I believe that if you want to wear a tie with your button collar oxford, that you should pair it with a sport coat. A blazer cut that is a little more casual, unstructured, or sporty will be the right pick. Equally, make sure the collar style on your shirt is right for a tie too: you don’t want a collar that’s too small lest you risk the tie bunching up the area around your neck.

The dress shirt, of course, does not have buttons on the collar. It also usually has collar flaps that are a bit larger and more pronounced, giving some room for the tie to rest with plenty of space, but with the corners equally able to be ‘tucked’ under a blazer, vest, or sweater. For me, the dress shirt is all about pulling the entire formal look together – it isn’t really the centerpiece because there isn’t really a centerpiece in this look. The entire fit is the point, the fitted and unified look is what really stands out. In a suit, every visible component matters in the way it fits into the other parts of the outfit. You could have an impeccably-fitting suit, but if your shoes are the wrong colour or aren’t polished, the entire fit starts to fall apart. Equally, a great dress shirt and tie can be totally bungled by a blazer that fits weird or doesn’t match with the pants. When the whole formal look is built with intention and attention to details, the look is elevated massively. Wearing pants, a blazer, shoes, and a good dress shirt that all fit properly will do wonders for your formal look – and it’s obvious to other people when they see you in the outfit. You can add little bits of personal flair to your formal outfits like this by focusing on the details, not the in-your-face aspects of the outfit. As such, a nice set of cufflinks, a unique tie, or even a highly-detailed pattern in your dress shirt will impress, especially when people get close enough to notice. It’s all in the details – people notice. 

Styles of dress shirts

For dress shirt cuts, there are usually three main criterion by which you can pick what type of shirt works for you. The most commonly found dress shirt cut is a more ‘regular fit’: this is a cut of garment that runs straight through from the chest to the waist. It gives a bit of space underneath and doesn’t hug the body too closely (or at all). This type of shirt can be a bit forgiving for those of us (myself included) that put on some unwanted quarantine pounds. Once layered underneath a blazer, vest, or sweater, the regular fit blends into the formal look perfectly. When you tuck it in, the waist has a bit of extra space and has a bit of a baggy look: for this reason I’d recommend wearing this type of dress shirt underneath a layer as wearing it without can give a bit of a baggy look that isn’t always conducive to modern formalwear.

The next type of dress shirt cut is the slim fit. It fits relatively snug around the shoulders, arms, and chest, tapering off slightly as it gets into the waist. This is a dress shirt meant to be tucked in if that can be managed (these can get tight), giving the whole look a bit of a pointed, directional look. This is a very common type of dress shirt cut in modern professional/formal menswear. Equally, given the structure that is offered with a slimmer fit, this cut of shirt does not necessarily need to be worn with a blazer to still look good. While I’d recommend some slacks or dress pants to keep it formal, wearing this type of dress shirt with a nice tie is a great way to keep it looking good without having to layer a heavy jacket overtop. For those of you that may work in an environment that is a bit warmer and the blazer can be annoying, the slim fit will help lighten the load. If you’re a gentleman with a bit of a larger chest, arms, shoulders, or waist, this likely isn’t the right cut for you. There’s no worse sensation than feeling like your formal outfit is choking you out from the inside: you want your formal looks to be structured, fitted, and comfortable. How are you going to bust a move at the wedding when turning around would risk splitting your blazer and shirt completely?

The last cut we’ll identify is a bit of a recent dress shirt style, meant as a bit of a middle ground between the slim and the regular. The ‘athletic’ fit is seemingly meant for those with a bit bigger upper bodies: athletic seems to imply a bit of muscle around the chest, shoulders, and biceps that may put strain on a slim fit but aren’t highlighted in a regular/relaxed cut (if you hit the gym 4 times a week you probably want to show off, I get it). With the wider upper body, the athletic fit takes a note from the slim cut and then tapers off quite drastically near the waist. This gives the entire outfit the illusion of being a slim-fitting look as it hugs the upper body the entire way down. Like the slim fit, this shirt can be worn without a blazer and still look solid given the close-fitting cut. 

Other things to keep in mind while you’re picking the right dress shirt for you is in the style of the collars. You want them to match with the other features of your formal look in order to create a unified outfit that comes together as a unit. If your blazer has relatively bold, large lapels, think about getting a dress shirt with collars that are a bit bigger so the shirt doesn’t feel like it’s drowning in the fabric of your jacket. In a business formal setting, you usually want to wear a tie, so make sure the tie you buy doesn’t clash with the rest of the look: muted styles, downplayed patterns, and matching colors are essential in this context. With business casual, you can often get away without a tie and dropping a button on the shirt. This gives you an opportunity to show off the shirt a little more and play around with color. You can have a bit of a personal flair added to the fit, perhaps wearing a brighter or bolder shirt – a salmon shirt with blue dress pants and a blue blazer, topped off with a nice watch and some brown dress shoes can be a really strong look.

Dress shirt examples

Now that we’ve learned a little about some of the basic cuts, rules, and ideas behind the different types of dress shirts we can start to delving into fitting and styling.

1. Formal Oxford Look

Just like we’d mentioned earlier, the Oxford isn’t totally limited to the realm of casual: wearing it layered with some properly-fitting blazer or sweater will do an excellent job of truly riding the line between hyper-formal and a little more relaxed. The mannequin on the right sports a classic-collared oxford with a striped gold and royal blue tie. The accents on the tie match with the sweater, all of which are complemented and tied together completely by the jacket. While this isn’t the right thing to wear to a black tie gala, it looks like it’d fit right in among fancy-schmancy English culture or at the Kentucky Derby. It offers an opportunity to still be dressed up but with a bit of lee-way for patterns and colors. This is a nice fit!

2. Business Casual Oxford

I think this is one of the best ways to wear an oxford dress shirt for anyone wanting to incorporate it into their closet. This gentleman is wearing a nice blue oxford shirt, unbuttoned once, underneath a well-fitting grey blazer. This is the ideal business casual look, perfectly at home in the office and the boardroom, but still comfortable and mobile. Equally, it can be worn to a nice dinner and have you relaxed as readily as stylish. Great look.

3. Black Tie Dress Shirt 

The classic. The most iconic. The standard. This is the way most of us would initially think about a dress shirt: white, crisply ironed, underneath a black blazer with a dark-colored tie. This is the fit you can wear to any formal event – from the fundraiser, the gala, and the evening award ceremony to the charity ball, this is a timeless way to wear the dress shirt. If you needed to wear it one way and only one way, wear it like this.

4. Business Formal Dress Shirt

This outfit treads the line between business formal and a slightly more casual look. It sits slightly above the oxford business casual look because the collar is more structured and retains a bit of the elegance and dressiness that you tend to look for in a dress shirt fit. Equally, you can play with color a little more: this person is wearing a relatively slim light blue dress shirt under a black blazer – this is a classic combo which likely wouldn’t ‘pop’ as much if it was just a white dress shirt styled the same way.

5. Formal Stylized Dress Shirt

This is a great way to wear the formal dress shirt without resorting to the classic (and occasionally stuffy) black tie look. The person above is wearing a crisp, slim white dress shirt with a striped tie under a formalwear vest. This outfit tends to highlight what I mentioned earlier about letting little details of your outfit stylize your look and make it a bit more unique. On its own this would still be a great fit, but with the addition of a few accessories it seems to become unique. I love the pocket square but more than anything, the chain brooch and the tie clip add the elements of detail and elegance that these fits need to retain. Equally, there is something personalized about wearing it like this – the entire look is still unified and nothing sticks out, but there are little elements of you sprinkled throughout. It’s all in the details!

6. Casual Dress Shirt Look

This is an excellent way to show off how to style the ubiquitous white dress shirt in a casual context. The beauty of using it like this is by offering a level of elegance and classic fashion to a comfortable outfit at place anywhere. The model is dressed in all white head to do, with a regular fitting white dress shirt (not oxford) tucked into white jeans with white sneakers, topped off with a white straw hat. With a few accessories like the metal bracelet and the dark sunglasses, a little bit of variation is thrown into this monochrome fit. The result is something that rides the classy wave but is equally comfortable and casual. This gentleman looks like he’d be at home on a beach in Cuba as readily as a fancy brunch spot. Great fit!

I hope this brief dive into dress shirts and their styling will help you figure out how to incorporate this iconic garment into your everyday.

With (and without) buttons on my collar, this is Graham. Thanks for reading.