How to Style a Dress Shirt

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Men's dress shirts are the standard for business wear and semi-formal occasions. Many men also wear them for casual occasions, especially with sleeves worn down and collars unbuttoned. 

Dress shirts come in a wide variety of styles, leading to a lot of decisions: Pocket or no pocket? Short sleeves or long sleeves? To tuck or not to tuck? Here are some standards for dress shirt styles to help you pick the right look for every occasion. 

What Is a Dress Shirt?

What is a dress shirt, anyways? Most of us visualize a button-down shirt with a collar. Past that, there can be some debate about what qualifies as a dress shirt and what doesn't. 

  • Polo shirts. Polo shirts have collars, and in some workplaces, they are acceptable workwear.  However, polo shirts are really considered a casual look, so although some workplaces may allow them, they cannot truly be considered dress shirts.
  • Short sleeves. Warmer climates are especially apt to view short sleeve shirts as dress shirts. They are acceptable in many workplaces in such climates and sometimes during the summer in cooler climates as well. However, short sleeve shirts aren’t really considered dress shirts because they mostly work better for casual outfits. If you want to adjust your wardrobe to warm weather, consider rolling up your sleeves and wearing a very breathable shirt instead. 

A dress shirt must have long sleeves, completely button-up,  and have a collar. Missing any one of these qualifications means that it isn't a dress shirt. Dress shirts are menswear wardrobe essentials and should be able to be worn with a tie and blazer, even if you aren't wearing a tie and blazer at the time.

What About Pockets? 

Can a dress shirt have pockets? The answer here is “maybe”. Very classy dress shirts never have pockets. This is a holdover from the old-fashioned perception that dress shirts were for gentlemen who had no need for pockets. Button-down shirts with pockets were for working people, safaris, and military, since they may need to carry something with them.

While button-up shirts today may have one pocket, it does reduce the formality of the dress shirt considerably. If you are wearing a dress shirt to a very formal occasion, choose to go without a pocket. Dress shirts with two pockets are not considered to be dress shirts. It doesn't matter how formal the sleeves, collar, and buttons appear, the presence of two pockets on the chest means that this is not a dress shirt.

How Should a Dress Shirt Fit?

The first fundamental to styling a dress shirt so that it will look great and fit the occasion is making sure that your shirt fits well. From your shoulders to your waist, a dress shirt should fit in a way that accentuates the best aspects of your body while downplaying any flaws. You don't have to pay for a custom-tailored shirt, but you do need to find a quality maker and choose your shirt carefully.

Torso

A dress shirt should fit your torso snugly. The buttons should lie flat on your chest, not pull or show any skin. The shirt should not be baggy or hang to one side or the other because it is too loose. 

If the shirt bags around your waist or leaves a lot of excess material when you tuck it in, it may also be too large or too long. You should be able to stretch fully and move around without having any siding material when you move back to your starting position. How a shirt fits largely determines the torso.

  • Traditional Fit. Traditional shirts have a looser fit and tend to have wider torsos and chests than other fits. They do not taper down as tightly as leaner cuts.
  • Tailored Fit. Tailored shirts have a slim fit that goes from the shoulders down to the waist, accentuating the lines of your torso.
  • Extra Trim Fit.  Extra trim shirts have a tighter fit that is ideal for more slender men. If choosing the shirt, it may be a good idea to pick a style that has a Dynamic 4-way Flex, since the stretch will give you more comfort in a tighter fitting shirt.

Collar Styles and Cuffs

Dress shirts come in a number of different collar styles, each appropriate for a different occasion. Style, cuff, and collar should all match one another and the event. Here are some style tips for different types of shirt collars to consider:

Wingtip Collar

This is the most formal type of collar, originally designed to be worn under tuxedos. These types of colors are almost never worn today except with a tuxedo or tailcoat. They are generally too formal for business wear. 

Point Collar

The point collar is among the most formal types of collar. It is also known as the Straight Point Collar. This is the collar that most of us think of when we are thinking about a traditional collar. These collars are narrow to accommodate a suit and tie seamlessly. 

The point of the collar is quite long, leaving the tips very close together. This formal collar is also quite versatile. It works well in business meetings or formal social occasions. Tie knots should be kept smaller when wearing this collar, and cuffs on these shirts should be round or angled.

Semi-Spread Collar

This is slightly more casual than the point collar, but it is acceptable on formal occasions. If your neck is on the long side, this may be the best collar for you. Have some fun with larger tie knots while still looking appropriate with the wider spread of the collar. Rounded or angle cuffs look good with this kind of collar.

Cutaway Collar

This collar has very small points and tips that are spread far apart. It has a sophisticated look, but is not as formal as other collars, because it lets you see the collar underneath the tie. Nevertheless, this type of collar is appropriate for many workplaces. This collar goes well with big tie knots and shouldbe worn with straight cuffs.

Long Spread Collar

The long spread isn't the most formal of collars. Still, it is a modern, sophisticated look that is appropriate in any work environment. This versatile collar can work with any tie knot and looks great with either straight or rounded cuffs. It looks good on most men, so it's a safe choice.

Button-Down Collar

This collar has buttonholes on the tips to fasten to the shirt, which is a style that used to be for sportswear but has made its way into businesswear as well. While this is still considered a dress shirt, it is generally not paired with a tie. 

Round Collar

The round collar is a distinctive look that was popular in the 1920s and is becoming popular in some circles today. It looks great with thin ties or under a sweater vest.

Sleeves

Dress shirts should have long sleeves, but there is a lot that you can do to play with how your sleeves look to make your shirt either more or less formal. Rolling your sleeves up to your elbows is a good choice for when you want to be more casual, but it can also be an indication that you are getting down to work at something more physical. 

How you wear your sleeves communicate something about your intentions, so be deliberate about wearing your sleeves to express your style.

Sleeve Length

Depending on the type of shirt that you wear and whether you're wearing a jacket as well or not, sleeve length and cuff style can vary. 

No matter how many buttonholes there are, the cuff should never go past the wrist. Cufflinks should be barely visible, and tucked right underneath the jacket sleeve.

Personal Style

Whatever cut and size you decide looks best on you, don't forget to keep your own personal style in mind when choosing the best dress shirt for your needs. You want to look professional at work, but that doesn't mean you can't let your personality show through a little bit. 

Contrast lining like this skull contrast shirt gives you a little bit of opportunity to express yourself, especially when you roll up your sleeves after work. These shirts are an excellent option for men who want to look professional in the office but be able to easily dress down their shirts for after-work drinks.

Choose Quality -- Whatever the Style

Whatever style you choose, you need a shirt that is made of the highest possible quality. The shirt you choose will say a lot about you in your workplace or with your friends and family, so you want a shirt that shows you care about how you look. 

High-quality shirts look great while providing benefits like resisting wrinkles and wicking away moisture. Breathable shirts like these keep you comfortable even as you move back and forth between a cold office and a hot outdoor climate. If you want to look and feel great while expressing your personal style, pick a quality dress shirt that speaks to you.

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Twillory