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Men’s Dress Shirts: When Should You Wear One?

They're called dress shirts, so shouldn't they only be worn on formal occasions? This couldn't be further from the truth. Dress shirts are a solid part of your wardrobe arsenal that can be deployed for many occasions. 

The trick to wearing the right shirt, in the right way, for the right occasion, is all about tweaking the style to fit. Here's what you need to know about when to wear a men's dress shirt.


Dress Shirts are Essential for Formal Occasions


If you're not sure whether or not you should wear a dress shirt, wear a dress shirt. It is always better to be a bit overdressed than to be underdressed. If you're going on a date, a dress shirt is hard to beat. 

It's challenging to dress up an outfit in an instant, but you can easily dress down if you wear a dress shirt. For example, this stylish Non-Iron Black Skull Contrast Shirtlooks appropriately dressy when it is buttoned-up, and the sleeves rolled down. However, when the sleeves are rolled up or the first couple of buttons undone, the skull pattern is revealed for a playful twist on this dress shirt. 

If you get to the party and feel overdressed, just roll up your sleeves and unbutton the first couple of buttons of your shirt to reveal your undershirt. Like magic, you are instantly dressed down. This is also a great technique to use when you are going from a more formal occasion to a less formal one. A dress shirt that can effortlessly transition from the office to after-work drinks makes your life easier. Be sure you choose a non-iron shirt unless you want your after workwear to be decidedly wrinkly.

If you want to make sure that you look as formal as you can for a very fancy event, choose something like a clean white dress shirt with a French cuff to show off your fanciest cufflinks. This is a great shirt to wear with a suit or even a tuxedo. It is sure to make you feel appropriately formal for any occasion.


Dress Shirts are Fun for the Club


If you think that the most appropriate wardrobe for the club is a T-shirt and jeans, you might be missing the point. Going to the club is an opportunity to break out the swaggier clothes and get some attention. You want to look classy, but you also want to rock the kasbah. What's the solution? 

How about an untuckable dress shirt that looks perfect with jeans, fits you perfectly to show off your moves, and gets plenty of positive attention? This Untuckable Glow Shirt features details that glow in the dark. Don't worry; you won't look like a highlighter with your entire shirt glowing. Only tasteful details in the buttons and some of the stitching in the fabric glows. If someone flips on the lights, you'll look like the most respectable person in the place with your stylish dress shirt.


Dress Shirts are Ideal for Many Casual Activities


Look your best no matter what you are doing with a great moisture wicking, non-iron shirt, with a bold pattern. A shirt like this is perfect for wearing on a boating trip, a hiking date, or anywhere else that you want to be active while looking your best. Choose an optional pocket if you want an even more casual look. 

Dress shirts are very functional for all kinds of outdoor activities since you can roll the sleeves up or down to accommodate the temperature. A moisture-wicking and hyper breathable shirt will keep you feeling as good as if you were wearing a workout T-shirt, while the wrinkle-free fabric ensures that you keep looking your best.


How Should a Dress Shirt Fit?


You won't look your best no matter what dress shirt you buy or where you wear it if it doesn't fit you well. Different fits look better on different men. Your personal preference will have a lot to do with what style you choose. Here are a few fits to choose from and which men they're best for:


Extra Trim

If you find that dress shirts seem to hang loosely on you, you may want to give Extra Trim a try. It is a very slim cut, with a triangular shape down from your shoulders to your waist. These shirts fit closely, but not tightly, throughout. 

Men who have narrow waists and slighter shoulders generally look best in this shirt. It should not be so tight that it is pressed against your skin. You should be able to grip a pinch of loose fabric without pulling across your stomach and abdomen.



The tailored fit is ideal for men who have broad shoulders that taper down to a narrow waist. It offers a slimming silhouette with enough room to move freely throughout the day. Many men in good physical shape and of an average size and build look best in tailored shirts. 

Tailored shirts offer a bit more room throughout the chest and abdomen than the Extra Trim fit, but they should not bag at all. If you can grab more than up to your second knuckle across the abdomen without pulling, it may be a bit too loose to fit you well.



The traditional fit is what our fathers and grandfathers grew up with. It is still a very appropriate cut for many men. The traditional fit cuts straight from the armpits down the body. It gives more room in the upper body and significantly more room in the abdomen. 

This is the best fit for heavier men or men who do not like to feel that their clothes are at all tight. It is acceptable for there to be a fair amount of loose fabric with a traditional cut, but the shirt should not appear to hang on you. The edge of your sleeve should never push past your shoulder. If it does, the shirt is too big.


Expand Where you Wear Dress Shirts!


Dress shirts are extremely versatile, comfortable, and classy. With the right dress shirts in your wardrobe, you may find that you're wearing them almost everywhere. Be sure to choose the right fit for you and seek out options that are free of wrinkles without needing to be ironed, and you're sure to love wearing dress shirts as much as you can.