Best Guide to Wearing Men’s Dress Shirts Casually

Best Undershirts for Your Shirts

Vestiary terms describe a long-sleeve shirt with a collar and front button down as a dress shirt.  

In everyday life, a dress shirt is known as the “good shirt” in your wardrobe. 

You pull it out for required formal occasions; whenever the dress code calls for a crisp, tailored suit, or sport it more casually, paired with jeans and white sneakers. 

Office events, weddings, and social gatherings would demand having a few of these versatile shirts on standby.

Below is a simple guide to wearing men’s dress shirts casually and a list of other casual men’s shirt options.


How To Wear a Dress Shirt In 4 Ways


The Business Professional Look

Business professionals always sport a tucked-in dress shirt with a tie, a full suit, or blazer and slacks.  Much like your dress shirt, it is crucial to find a suit that is the right fit for your body.


Business Casual Dress Shirt

When wearing a business casual dress shirt, choosing conservative colors is best (i.e.) whites and blues, bearing in mind that you can never go wrong with white.  Small checkered patterns are also a safe play with this look. 


Business Casual Look for Men

Business Casual dress is similar to a professional business look but without a tie and sometimes even a jacket.


The Office Casual Dress Shirt Attire

Office casual is similar to business casual but a little more relaxed. Once again, the fit of this look will be essential as you will never be wearing a jacket or sports coat. Instead of slacks, office casual gives you the flexibility of wearing different types of pants. 

Over the past few years, Casual dress shirts have become acceptable in some offices. This look is perfect for leisure events or weekends. 

How the above outfit fits are critical to the final look. We cannot stress that enough; fit always comes first!



Can I Wear a Dress Shirt Casually?

Over time we have noticed a shift from the traditional “suit and tie” toward a more casual and unique dress.

 Feel free to experiment with vivid colors and patterns when wearing a casual dress shirt, and undo as many buttons as you feel appropriate for the occasion. We encourage you to wear the dress shirts you love with a casual touch and ditch the tie!


Wear it untucked.

In the case of casual, sophisticated, and confident dressing, the untucked shirt fits right in it and is no longer considered sloppy.

Wear it with the sleeves rolled.

Want to ace the attractive casual look? Pair your dress shirt with white jeans and casual shoes.

Wear it with a sweater for a sleek and simple look, like under a light grey blazer cardigan, for an impressive achromatic look. 

Wear it short-sleeved. 

Add a few short sleeve dress shirts to your mix. Perfect for holidays and weekends. Throw on a pair of leather sandals and a classic straw hat, and they still look put together.


How Do I Choose a Dress Shirt?

When the shirt fits under the armpits and across the upper back, gives you a full range of motion and fits comfortably around the chest. Those kinds of shirts are known to be the best-fit shirts.

A fitted shirt will feel snug but not tight.  The chest should “fill out” the shirt in a way where your body is discernible under the fabric.

So if you are a big guy or a small guy, before you even think about shopping for a new dress shirt you need to be sure of your shirt size. For accurate results, have your measurements taken by a Tailor or friend. 

You want a shirt that permits a wide range of motion and shows off your body in a flattering light. Three of the most in-demand men’s shirts you will find are slim fits, regular fits, and loose fits. Other factors in selecting dress shirts that best suit you are your fabric, color, and pattern. For your fabric type, most guys will opt for a typical Oxford or Poplin dress shirt for any occasion year-round, from daily office wear to weddings and other special events.

There is no argument where color and pattern choices are a concern.  A plain white dress shirt is iconic for men. This is the measure by which all dress shirts are measured. It speaks toformality and flexibility. Every man’s closet should have a staple of a white shirt. Be it that you wear a suit every day or rarely. Solid-colored dress shirts, to a great degree, white and blue, are the bedrock of executive men’s clothing. 

He needs to have a variety of these and always a spare at the office.


Nine Best Types of Men’s Shirts to Consider

Oxford Button-Down Shirt

A dress shirt is a stiff collared shirt with long sleeves that can be worn with a suit or blazer.

Oxford Shirts are usually considered dress shirts. Still, there are two ways that the Oxford shirt differs from a regular dress shirt:

They usually have a button-down style collar, eliminating the problem of collars flopping around or laying flat and disappearing underneath a Jacket collar. The Oxford Shirt derives from a specific weave of the fabric called, you guessed it, Oxford cloth. It has a basketweave structure and a lustrous aspect making it a popular textile for a dress shirt.


Cuban Collar Shirt

A Cuban collar shirt has a more relaxed, open collar, short sleeves, and a straight hem. It provides a casual-smart look that has proven flattering on all body shapes by broadening your upper body and running straight down your sides. The distinctive collar screams casual – there is no top button for starters, and it provides a dandy-vibe look that will set you apart from the others. 

It has a similar silhouette to retro bowling shirts, also touristy Hawaiian shirts but with a bit more class. These shirts are ideal for garden parties, sunny days, and nights.


Over shirt

An overshirt is a hybrid between a shirt and a jacket.   Which proves to be an unsuccessful combination called a ‘shacket’ in some areas of the industry. The versatile ‘overshirt’ is typically made of a slightly thicker material than regular shirts for men and is understandably heavier and more durable. In some cases, overshirts are made from non-traditional materials depending upon the retailer and the style.

Men’s overshirts bridge the style gap between jackets and shirts. Functional and easy to wear, they are handy when the change of season comes around. Overshirts are sometimes worn over a t-shirt or under a coat. 

They come in multiple prints, patterns, and designs; other options encompass lumberjack, cowboy, and utility-style directions. The collection varies in fabrication and colors from cotton and denim to fleece and padded.


Flannel Shirt

Like some other fabrics, flannel has been around for years. It is a soft woven fabric made of wool or cotton and slightly milled and raised.

It began with farmers and the working class, who preferred it for its warmth and affordability. As the fabric advanced through the years, a check print was introduced and soon became its signature style.

Today, flannel shirts are still a favorite item for their comfort and effortlessly cool style; They have become a worldwide addition to every gentleman’s closet.



Classic Short sleeve shirt

Short-sleeve dress shirts have partial sleeves. Typically extending halfway to three-quarters of your biceps, unlike the long-sleeve dress shirt, which covers your arms completely. Short sleeve shirts are perfect for wearing in the summer or on hot days. 

Ideally, they are perfect for casual occasions, but because of their button-front feature, it also displays a formal vibe.


Denim Shirt

denim shirts are cotton fabrics made up of two different yarns, constructed using a “twill weave,” which involves multiple strands of Yarn woven together. The result is a thicker, more structured fabric, often associated with a casual, rugged style. It is sometimes confused with the chambray shirt made from a plain weave. 

The best thing about denim shirts is their versatility, no questions asked. You can be creative by pairing them with various things.


Linen Shirt

Perfect for the summer and warm, dry climates. Linen is soft and breathable.  Contrary to cotton, it feels crisp initially but becomes softer and more malleable over time.  Linen boasts strength (longevity) and weight that allows a beautiful dress shirt to drape.

Linen dress shirts are formal or semi-formal button-up shirtsThese dress shirts are lightweight and weigh less than nearly all other types of dress shirts, including those made of cotton and wool. 

Men’s linen shirts are the keys to truly and figuratively unlocking the most refreshing summer outfits.


Polo shirt

A Polo shirt is said to perfectly bridge the gap between a t-shirt and a classic oxford shirtThere is often quite an overlap between work and play. A polo shirt is a shirt with a collar, a placket neckline typically with two or three buttons, and an optional pocket. 

Polo shirts are usually short-sleeved; polo players initially used them during the 1920s.  In contrast, a style of fabric shirt with a T shape of its body and sleeves is called a T-shirt. The Traditional look is short sleeves with a round neckline. This is known as a crew neck; it is collarless. 

Usually made of a stretchy, light, and inexpensive fabric, T-shirts are easy to clean. Polo shirts and t-shirts are two common types of casual shirts that everyone wears. 

T-shirts have various designs and styles, but polo shirts are typically standard. The difference between polo and t-shirt is their design. Polo shirts usually have a collar and placket with two or three buttons beneath the collar, whereas most t-shirts are collarless.



Chambray is a cousin to denim. The Chambray shirt is a cotton plain-weave fabric with dyed warp Yarn and a white filling yarn.

Chambray is traditionally light blue but is available in various fashionable colors. Denim looks much like chambray, which is more delicate and woven differently. It is generally lighter than denim and usually made of cotton, linen, or cotton/linen blends.  

Ideal for summer shirting as the plain weave and natural fibers breathe and allow cool air to pass through. There are tactile benefits, too. 

Typically, very soft and smooth to the touch due to a finishing process where the cloth is heavily pressed, which gives it a subtle sheen.


Can You Wear a Dress Shirt Untucked?

It’s easy for an untucked dress shirt to be interpreted as unprofessional. However, that is not to say it is a totally inappropriate look. 

Given the right time and place, the untucked dress shirt can reflect a casual and stylish vibe. Consider that it is more of a casual look and not to be confused with a business casual look. Shirts that have a flat stitched hem are to be worn untucked. 

However, if the shirt has visible “tails,” it is safe to say shirts with hems that have varying lengths and are even all the way around; should always be tucked in.

Wearing a shirt with tails untucked is not a forbidden look; However, it is a juvenile one. 


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