A tailored dress shirt is essential to any man’s wardrobe and a must-have for formal events or business meetings. However, it can sometimes be a little unclear what constitutes a dress shirt with so many colour options, fits, collar types, and fabrics available. 

The master tailors at Phillip Alexander have put together this guide with everything you need to know about dress shirts, including:

  • What is a dress shirt? 
  • What is an Oxford dress shirt?
  • How should a dress shirt fit?
  • How to style a dress shirt


What is a dress shirt?

Put simply, a dress shirt is a staple of every gentleman’s wardrobe. It’s a semi-formal or business style of shirt which can be worn to formal, semi-formal and casual occasions. Dress shirts are incredibly popular and can come in a range of collar and cuff types to suit different levels of formality. They are always long-sleeved, buttoned-down shirts. Short-sleeved dress shirts are sometimes seen, but these should not be paired with suits. 

Dress shirts:

  • are commonly made from high-quality cotton or silk.
  • are longer in length than casual shirts.
  • usually come in light, solid colours, such as white or light blue, plain darker colours, or subtle, vertical stripes.
  • can be worn to various events, including business meetings, weddings, and parties.


The dress shirt’s collar is one of the most important elements and affects the overall appearance and the shirt’s formality. Here are a few of the common types of dress shirt collars:

  • Point collars – one of the most common options. Point collars sit close to the neck and are narrow, so they can be worn open to casual events or with a tie for more formal occasions.
  • Spread collars – these are a more formal option and sit further away from the neck. A spread collar is traditionally only worn with a suit.
  • Cutaway collars – this collar features an eye-catching V-shape and a wider collar width so that it can be worn with ties and bow ties to formal events.
  • Winged collars – this is the most formal collar choice for men and can be worn with a bowtie to black tie events. 


What is an Oxford dress shirt?

Even if you’ve seen or worn an Oxford dress shirt before, you might not have realised this. The name refers to the type of fabric the shirt is made from. This fabric was originally made in Scotland and has a rougher weave (known as a basket weave) than other dress shirt fabrics. This makes Oxford dress shirts stiffer and more durable than other dress shirts. They’re also popular for winter or outdoor events because of their warmth. 


How should a dress shirt fit?

A tailored bespoke dress shirt is the best way to ensure a precise and flattering fit. However, if you’re buying off-the-peg or have an existing dress shirt in your wardrobe, here are our top tips to ensure it fits correctly.


Chest and waist 

Your dress shirt should fit comfortably across your chest and upper back, allowing a complete range of motion. Although it should feel snug, it should not feel tight and uncomfortable. 

To create a clean line, it should taper from your chest to your waist. No excess fabric should be visible when your shirt is tucked in.



A dress shirt should have enough length to be worn tucked or untucked according to the occasion. When tucked in, the shirt hem should be long enough so that it does not pop out when you raise your arms above your head.



The shoulder seam of your dress shirt should be close to the top of your shoulders. If it rises towards your neck, your shirt is likely too tight. Your shirt is likely too large if the seam slides down towards your arm. 



Your collar should not be too tight. You should be able to button your dress shirt comfortably with enough space for two fingers to fit between your neck and the collar.



Men’s dress shirts typically have a high armhole to create a tapered sleeve that elegantly follows the contour of your arms. If you notice excess fabric hanging underneath your arm, this is a sign that your shirt is too large. Similarly, it should not be so tight as to restrict the range of motion of your upper arms.

When buttoned, your dress shirt cuff should fall at the base of your thumb. However, the sleeve length can also depend on personal preference. 


How to style a dress shirt?

How you style your dress shirt will depend on the formality of the occasion. Dress shirts are incredibly versatile and are easy to dress up for formal events and dress down for relaxed days out. 


Formal events

Formal attire is usually required if you’re attending a formal wedding or event. This is typically a black or navy suit with a white dress shirt. Depending on the event, you might add some colour to your outfit with a tie or pocket square and complete your ensemble with cufflinks and a statement watch. 

If you’ve been invited to a white or black tie event, you’ll need to follow the appropriate dress code. We’ve got guides on white tie and black tie etiquette to help you out. 


Semi-formal events

Feel free to get more creative with your colour choices for semi-formal events. You’ll likely want to leave the tie at home and add a less formal blazer or even chinos. 


Business casual  

How you choose to wear your dress shirt at work will depend on your office’s dress code. This might involve a formal suit, tie and white or shirt, or a more relaxed fit with a blazer and no tie. 


Smart casual

Oxford shirts also look great paired with tailored trousers or chinos for days out and evening meals. They even work with smart shorts for warm, sunny days. 


Casual wear

Although dress shirts are considered formal or business wear, this doesn’t mean you can’t wear them more casually. Dress shirts, especially Oxford shirts, are perfect for layering in the autumn and winter. You can pair them with a knitted jumper and dark jeans for a relaxed fit. In the summer, why not try rolling up your sleeves, unfastening a few top buttons and leaving your shirt untucked?


Expertly tailored shirts by Phillip Alexander 

A well-fitting dress shirt is an incredibly versatile fashion staple every man should have in his wardrobe. Opting for a bespoke tailored dress shirt is the best way to guarantee the perfect fit, however, you choose to style your shirt. 

At Phillip Alexander, we’ve been dressing gentlemen for over 150 years. Whether you need a dress shirt and suit for a formal occasion or for everyday wear, we can create an expertly crafted garment suited to your needs!

We have locations in Cheshire and Savile Row in London and offer various tailoring services, including bespoke shirts, bespoke suits, semi-bespoke ‘made to measure’ suits, and tailored suit hire

Bespoke tailored shirts

Our bespoke tailored shirts are handmade by our master tailors for the perfect finish. Every shirt is individually tailored to your precise size and shape to ensure a seamless fit. You’ll have complete control over the fabric, cut, and details, resulting in a unique suit that’s exactly as you envisioned it. Our world-class tailors can assist you with your bespoke shirt design and offer any styling advice you need if you plan to wear your shirt to a specific occasion.

For the complete bespoke experience, pair your bespoke shirt with one of our stunning bespoke tailored suits. 

To learn more about our range of services or to book your initial consultation, get in touch with us today.