What To Wear With Black Dress Shirts?

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When it comes to men's dress shirts, the classic black dress shirt is a must have for every man's closet. The traditional black dress shirt isn't only for the big & tall or slim fit either- there is something in between for everyone. The men's dress shirt is more custom than you'd expect. 

The traditional non-iron, black dress shirt is a timeless wardrobe staple, but since there are so many different ways that you can wear a black dress shirt, there are a lot of ways that you can wear it wrong. But there are also a lot of ways to wear it right! This article will help you find the right style of black dress shirt and guide you in the right direction so that you look timeless and classic no matter the occasion. 

Best Stretch & Non-Iron Black Dress Shirts For All Occasions:


Black Dress Shirts: How to Find the Right Style

When looking for a black dress shirt, there are many different factors you need to consider before you even get started. It might be a good idea to brush up on general dress shirt tips and tricks, as well as make sure that you have the right measurements. Once you have the right measurements for your dress shirt (collar and sleeve length), either by using a dress shirt that you already own, getting professionally measured at a tailor, or measuring yourself at home with the help of a friend, you are ready to get started finding the perfect black dress shirt. 

Knowing your measurements will help you to find the perfect fit. When a dress shirt looks messy, it's usually because the fit is wrong. For example, someone who is wearing a regular fit when they should be wearing a slim fit. Or someone wearing a long sleeve shirt with cuffs going past their wrists. It sounds like it wouldn't be a big deal, but finding the right style for your black dress shirt can make or break your look. 

What Type of Dress Shirts are There?

You really can't go wrong with men's dress shirts these days. And it's no secret that there is an abundance of dress shirt styles. They come in a variety of shapes, colors and collar types and the best sellers are always revolving as supply chains and fashion trends do. Whether you're looking for a long sleeve dress shirt, short sleeve dress shirt, point collar, or a simply a plaid dress shirt there is something for everyone. 

The traditional non-iron black dress shirts can be the perfect pairing for a tuxedo or to wear on its own. We've seen a button-down collar dress shirt paired with a sport coat or a blazer which is the perfect example of balance when it comes to a black dress shirt. A few factors to consider are the occasion, fit, fabrics, patterns and of course the pairings to complete the look.  

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The first thing that you need to consider when buying a black dress shirt is the occasion that you are purchasing it for. Are you going for a more casual look for a date? Consider a spread collar and regular fit. Or are you looking for a really formal look for a special event like a banquet or gala? Try a long sleeve french cuff or a point collar. Your answers to these questions will help you with the rest of your search, so make sure you nail this down before you continue on! 



The next thing that you need to consider before buying a black dress shirt – or any men's dress shirt for that matter – is finding the right fit. There are regular fit dress shirts, slim fit, and even stretch dress shirts. A lot of this will depend on your body type but some of it will depend on the occasion and function that we discussed earlier. Generally, there are three different main types of fits for dress shirts. 

These are the classic fit, the slim fit, and the modern fit. However there is also a slim fit stretch as well as regular fit stretch and pretty much everything  else in between. There is also a newer more casual regular fit style that is termed the “untucked” shirt that is actually meant to be worn untucked instead of tucked into your pants. In contrast to this more modern style, the classic fit is the most traditional of all the fits and was created when men only wore dress shirts under their suit jackets. 

As a result, the classic fit is baggier than all of the other fits and can be a good option if you are larger in size, if you need more room to move around or stay cool, or if you are going to be wearing a jacket with your shirt. However, be cautious when choosing the fabric for a classic fit dress shirt. Since the extra fabric can easily wrinkle you’ll want to consider a classic fit dress shirt in a non-iron fabric. 

The next fit is the slim fit which is a good option if you are slimmer or big & tall and do not plan on wearing a jacket or tuxedo with your dress shirt. This is a cleaner and more modern look that is really in-style right now. But at the same time, it can be more restrictive than the other options such as the regular fit. 

The last fit is the modern fit, which is essentially a nice mix between the classic and the slim fits. The modern fit looks good on men with an average build – as there is some room in there to move around but not too much that it looks baggy and unkempt. This is also a great option if you want a really versatile shirt that you can wear with or without a jacket. It's important to remember that every brand will have a different fit from the next. Meaning the Calvin Klein black dress shirts will have different fits than a Kenneth Cole black dress shirt. That's why we recommend getting your shirts custom sized. 



Once you have decided which fit is best for you and the occasion that you need the shirt for, you can move on to picking the right fabric. There are three main types of fabrics for dress shirts: cotton, cotton/polyester blend, and performance. Cotton is the most traditional choice and looks and feels really nice. Cotton is also really breathable and can keep you cool. However, cotton wrinkles easily which can be an issue if you will be seated for long periods of time. 

Cotton/polyester blends are one of the best sellers for a traditional men's dress shirt. It's an alternative to all cotton that is often cheaper but still looks pretty nice. However, it can be a lot warmer than cotton and is more insulated instead of breathable. At the same time, it doesn’t wrinkle as easily as cotton does. 

Finally, there is a performance shirt which is a relatively new feature when it comes to dress shirts. Performance shirts are made with moisture wicking technology that helps take sweat away from your body and onto the outer surface of the shirt where it can then evaporate. They're known to be non-iron, wrinkle free and most of the time they make up the slim fit dress shirt. 

These shirts are soft, light, cool, and wrinkle resistant. Depending on your own body and the occasion you will be wearing the shirt, one of these options might be better than the other – but overall, it’s up to you and how you think each fabric feels against your skin. In any case, it’s always worth investing in a great quality dress shirt that feels soft and looks good! 


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The next thing that you need to consider when looking for a black dress shirt is the pattern of the shirt. Depending on where you plan on wearing it, patterns can be a great way to enhance your look and make a statement with your ensemble. Buying a black dress shirt with a nice pattern like plaid is a great upgrade to the solid dress shirt. While traditionally dress shirts come in patterns like stripes or checks, a black shirt is a great opportunity to try out different non-traditional patterns like floral or paisley that you might have been hesitant to try out before.  



Finally, we will go over exactly how to wear your black dress shirt to create the best look based on your overall style and the function of the shirt as well. Who wouldn't want to swipe their credit card to add to their wardrobe if it means staying up to date on style? Of course, trends come and go and new arrivals are constantly showing up on the shelves. 

Probably the best thing about a black dress shirt is how versatile it is – it can really be worn with anything! Pair it with a tuxedo, bomber jacket, or simply your favorite pair of jeans. As a wardrobe staple, the options are endless so we will break down a few of the most popular combinations. Starting with the casual options – a slim black dress shirt (patterned or otherwise) will look great with black or dark blue denim pants. 

This is also somewhere that you could go with an untucked option as well. Another good look is pairing a spread collar black dress shirt with a classic patterned sweater vest. As a semi-casual option, you could pair a plain black dress shirt with black dress pants for a classic look. Moving towards more formal, you should pair a black dress shirt with an all-black suit look and a sleek black tie or black bow tie. 

When in doubt – pair black with black! That’s definitely a safer bet than pairing it with dark colors like red, brown, dark green, or navy (except for jeans). You should also never pair a black dress shirt with anything white unless you want to look like a waiter. Overall, with the right styling and attention to detail, you can easily rock your black dress shirt and utilize your new wardrobe staple for events as casual as a night out on the town to a night out at the ball.

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