A Gentleman's Evening Guide: Picking the Right Dress Shirt

A Gentleman's Evening Guide: Picking the Right Dress Shirt

The proper shirt has its rightful place in men’s wardrobes. Read this gentleman's guide to picking the right dress shirt styles.
Keyword(s): dress shirt styles

Dress Shirt

Don’t think men care about how they look? Think all dress shirts follow the same, boring, office-appeasing look?

Although the fashion industry is more female-oriented, evidence suggests that men care as much about it as women do. In fact, they even spend more on their clothes than women. This suggests that while they may not be as obsessive to the latest designs and trends, they still care about turning up for the occasion looking their best.

If you’re out for the evening, for instance, you’d want to make sure you have the right dress shirt to look presentable. However, with all the dress shirt styles in the market, how would you pick the right one to wear?

It can be confusing, but with the ultimate guide below, you’ll know what to look for in evening attire. Keep on reading to see how you should choose the right shirt to wear.

1. How to Choose the Proper Fit

The fit may be the most important feature of men’s dress shirts. No matter well-made it is with the most exquisite details, it will look bad if it doesn’t fit well on your type of body. Below are the most common types of fit and when they’re appropriate.

Classic Fit

The classic fit offers generous room all throughout, including in the arms, chest, and body. It has a broader cut across the shoulders and has an overall boxier shape. Because of these qualities, a classic fit dress shirt is the most comfortable out of the other types of fit.

This was the common shirt style in the past, but only because people back then always wore a jacket on top of it. The jacket hides the fact that it doesn’t fit well. Plus, people preferred comfort over the looks of a shirt that remained hidden.

Today, it’s still great to have one in your wardrobe to wear under your jacket. It’s also flattering for those with a rounded or muscular body type. It’s the best fit to wear if you’re going on long hours of meeting or flights.

Slim Fit and Super Slim Fit

As you would guess, this one is best for individuals with a slim body type. If you have a rounded belly, it will show through this shirt, thus it may not be right for you.

Unlike a classic fit shirt, this one sits closer to the body without being tight. It has features like a high armhole stance and an accentuated back with darts. It may have a yoke that’s narrower and a marked tapering at the waist.

The downside is that it’s not as comfortable and it restricts your movement. However, this allows you to wear it without a jacket as it looks better as is. You may wear it to cocktail parties or other social events where you won’t move much.

Then there's a super slim fit that provides a skin-tight feel, enhancing the body silhouette. For this reason, it’s the least comfortable shirt with more restricted movements.

The only body type that would do this justice is the skinny type. People with other body types would have to steer clear of this one.

Contemporary Fit

If you want both comfort and looks, a modern or contemporary fit is your best bet. It’s tapered at the waist, but it provides more generous room in the sleeves and body.

It’s stylish enough that you can wear it without a jacket. Still, it provides comfort and mobility to allow you to raise your arms if you need to.

This fit would look best on people with an average build – not skinny yet not too round, either. It may also be better for occasions wherein you would need to dance or make a toast, such as weddings and bachelor parties.

How to Check if It’s the Right Fit

Whichever fit you choose, you should still always check if it fits well on your body. If you get a slim fit, for example, should feel tighter on the chest and the sides. There should be almost no excess fabric at the back, as well.

When you try on a shirt, try bending your arm; if the cuffs ride up on your arm when you do this, the sleeves are too short for you. Now, put your arm back down and see how far the cuffs go past your hand. If it goes past 1 inch, that means the sleeves are too long for you.

Check how big the cuffs are, as well; if your hands fit through without you needing to undo the buttons, it’s too big. Try putting 2 fingers between the cuff and your hand as well; if they fit, it’s also a sign that the cuffs are too big.

When you raise your arms, the shirt tails should also not come out of your pants. Try other movements, as well, and see if they will slip out.

2. Choosing the Color and Pattern for the Right Occasion

White is the most common shirt color, and that’s because it’s safe and appropriate for any occasion. If you want to switch it up, though, you have to take into account the event you’re attending when choosing the design.

Men’s shirt styles in solid colors, such as blue, pink, and lavender, are great today for businessmen and the likes. Off-white is also a good choice; it may even be better than white if you have yellow teeth. A white collar will highlight the yellowness of your smile more.

For evening wear, a white shirt is the most popular, with people being more playful with jackets. Some may wear a darker-colored shirt, but only a few can pull this look off. Men have to look at their features, too, like their complexion and eye color to see which color would suit them best.

Dress shirts are also available in patterns, but remember that the more design a shirt has, the less dressy it is. Striped shirts, for example, may not work on cocktail parties, but they’ll still look great in an office.

Checked shirts are more casual, perfect for a day or night out on the weekends. Shirts with other designs may be even more casual, and so they may not be appropriate at all in business or formal functions.

3. Collar Styles and Variations

All these types of dress shirts are available in 2 basic collar variations: point and spread. Choosing the one that suits you is important since it’s the closest to your face, attracting more attention than the other areas. Furthermore, it’s one of the few parts that stick out when you wear a jacket on top.

The most common collar style is the point collar, in which the edges point downward at a 60-degree angle. The points at the top sit close together, sometimes to the point that they hide the upper part of a tie.

On the other hand, a spread collar spreads downward farther at a 90-degree angle or more. The points have more space between each other, revealing more of the collar band.

You can further break down these 2 styles into more variations. Some collar styles, for example, may have a button on each tip, and some may have 2 buttons on the band.

A wingtip has the collar points folded out, resembling wings. These are more appropriate for black tie events, worn under a tuxedo.

4. 2 Types of Cuff Styles and Why They Matter

For cuffs, there are also 2 basic styles: button cuffs and French cuffs. The latter is more formal, although some shirt styles that are less formal have also adopted French cuffs. The reason for that is because this cuff style allows gentlemen to wear cufflinks.

Button cuffs, on the other hand, are those that you button into place. They may have 1 or 2 buttons and are better for more casual wear. Depending on the style of your shirt, this can also be appropriate in an office setting.

The cuff style is important because aside from the collar, it’s the only part that’s visible after wearing a jacket. Many people prefer French cuffs because of this. Furthermore, they also allow wearers to be creative with their cufflinks.

5. Hem: Do You Tuck It In or Leave It Untucked?

The hem of a shirt is usually tucked in, but some styles allow wearers to leave it untucked. You can wear shirts with straight hems, for example, without tucking it in and it will still look great. However, it’s only appropriate for casual wear and on relaxed occasions.

6. Dress Shirt Fabric and Weave

The next consideration of your dress shirt style is the make, with cotton and linen as the most common types. Cotton is the best choice because of the comfort it provides and its smoothness. It exhibits good heat and moisture conduction, absorbing up to 27 times its weight in water.

When attending black tie events and other evening social gatherings, a cotton fabric should be your shirt of choice. Cotton also responds to ironing well, but the caveat is that it may be rather pricey.

For less formal events, however, linen and man-made fibers are acceptable. Linen might even be more durable, and it has a good liquid absorbency rate of 20%. It also allows for airflow, but they retain heat so they’re more suitable in the fall and winter months.

Man-made fibers won’t have the desirable traits of cotton at the same level, but they still present some advantages like the rock-bottom price and they’re often stain- and wrinkle-resistant.

7. Other Dress Shirt Styles Details You Need to Consider

Other than the basic features above, there are more factors in the design you need to consider. Although they’re not as big and important, they can still contribute to how your dress shirt looks as a whole.


Deciding over the pocket is quite simple; if you want to go formal, choose a shirt with no pockets, otherwise, go with 1 or 2. The more pockets a shirt has, the less formal it is, so those with 2 pockets isn’t suitable as your day-to-day office wear.

Shirt Plackets

Another element in the front of the shirt is the placket, the fabric edge with the buttonholes. Its standard design, also called traditional or American placket, consists of a fabric raised off the dress shirt itself, with stitches at each side holding it.

While that’s perfect for casual wear, men prefer French plackets for evening shirts. It makes for a more polished look because of its simplistic design. The edge of the fabric folds underneath the shirt with the buttonholes stitching it in place.

There’s also a less popular style called the Fly Front placket, which has extra fabric hiding the buttons. It can be appropriate for evening shirts, but it’s not as timeless as French plackets.


Speaking of buttons, this element is also worth a second thought. As small as they may seem, the wrong choice can distract other people or even ruin the whole look.

There’s only 1 question to ask here, though, do they draw attention? If they do, then they’re not the right choice, unless that was what you’re going for.

Of course, that’s aside from their function and durability. If you want your buttons to last, choose one made with high-quality resin or Mother of Pearl. Most buttons today are plastic, though, and they can do the job quite well even though they’re less durable.


The position of the pleat or the absence of it differentiates the 3 back styles in dress shirts. The most common is the single large double pleat on the center, which helps the shirt fit better on most body types.

A double pleat is better at this function, though, and its high price reflects that. The pleats sit on the shoulder blades, contributing to better aesthetics.

The last type is the one without pleats, which is usually custom shirts. Because the shirt already matches the person's features, there’s no more need for pleats.

Found the Right Dress Shirt for Your Evening Attire?

Now that you know which of these dress shirt styles are appropriate, it’s time to shop for that perfect shirt. Take a look at our vast selection of shirts and other men’s wear, such as blazers and shoes. If you need any help or if you have a question, don’t hesitate to contact us.

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