Should You Wear A Black Shirt? (Classic Men’s Style Tips)

We believe that black is one of the most overrated colors in menswear. Not because we don’t like the color black – we’re the biggest fans of a classic Black Tie ensemble – but because black in modern menswear is often employed in boring and uncreative ways; either in an effort to appear business-like and dignified or in pursuit of a fashion-forward, futuristic style. So, should wear a black shirt?

In practice of why black suits and black shirts are such a mainstay in trendy celebrity fashion, George Clooney, Christian Bale, and Idris Elba can be regularly seen in black shirts and remains a fixture in action films like the John Wick series.

But, despite how popular it is in modern menswear, black shirts were rarely worn as a part of classic menswear – likely because black as a color was so closely associated with formal wear. So, gentlemen of classic style pursued other color palettes and non-formal attire.

An illustration of a gentleman in the 1930s in a Black Tie attire
An illustration of a gentleman in the 1930s in a Black Tie attire

Precisely as a revolt against the classic style conventions, the “Man in Black” Johnny Cash wore all black stating, “I wore black because I liked it. I still do, and wearing it still means something to me. It’s still my symbol of rebellion against a stagnant status quo – against our hypocritical houses of God, against people whose minds are closed to others’ ideas.”

This sense of rebellion also influenced subcultures known for wearing black – in the beatniks and folk-rockers of the 1950s and 60s to the more recent goth and emo cultures. The black shirts are worn for trendy modern fashion or as a way to revolt against the status quo.

Is it even possible to make them a part of classic menswear? We believe that it certainly can be done, but there are some caveats. 

There are several situations in which you might be expected or required to wear a black shirt. These can include as a uniform in certain service industries or for a musician’s concert black dress code; as a part of certain religious traditions, whether as a traditional garment or attire for a clergyman, or any circumstances and where you’re obligated or reasonably expected to wear a black shirt.

Obviously, a black shirt is perfectly acceptable on those occasions, but what if you’re not a Lutheran priest or not getting ready to play a medley of Sousa marches? Can you make a black shirt work for you as a part of classic style?

Preston, our Content Director and a jazz singer, in a black dress code ensemble
Preston, our Content Director and a jazz singer, in a black dress code ensemble

Let’s start out by first highlighting the pros and cons of the black shirt. Black is probably so popular because it’s elegant and stylish. There’s a reason why it’s the primary color in both Black and White Tie. It imparts a sense of gravity and dignity and helps to emphasize the other details of your outfit – like a pure white shirt and red boutonniere.

Black Shirt Pros

1. Black Is Refined

We suspect that many men wear black shirts because they believe that black will add an air of formality to their outfit, and we agree that it does. Although, we feel that even more appropriate formality can be added when paying attention to the appropriate dress code for that occasion. 

2. Black Shirts Are Versatile

The little black dress is a mainstay in women’s fashion because it’s easy to accessorize and complements nearly all skin tones. To a certain extent, the same is true for black shirts for men. 

A black shirt won’t glaringly contrast with many other colors. Although, we’ll note that it usually won’t complement other colors very well either. Essentially, not looking bad, but not looking great either

A 1994 photo of Princess Diana in a black gown [Image Credit: Vanity Fair]
A 1994 photo of Princess Diana in a black gown [Image Credit: Vanity Fair]

Black’s also a simple fit for many skin tones, except for those with extremely dark or extremely fair complexions.

3. Black Is Modern

There’s no denying that a sleek, simple silhouette of a black shirt is distinctly a modern style. We suspect that there’s just something about black that is both primal and futuristic; a powerful color that, because of its functionality and clean lines, seems perfectly suited to the closely-tailored, trimly-cut, and skinny details typical of contemporary suit styling.

Black shirts also exude the confident, casual attitude of contemporary menswear, fitting well with modern style cues like going tieless, pairing a blazer with jeans, or wearing sneakers with a suit. Of course, we have to note again that if something is listed as contemporary style, it’s difficult for them to be a part of the classic style.

Chris in a modern casual look featuring a black dress shirt
Chris in a modern casual look featuring a black dress shirt

4. Black Is Vintage

In the 60s and 70s, the subdued palette of the jet-set look, the increasing casualization of menswear, and the influence of beat culture brought on a bit of a moment for black shirts.

These shirts were casual and included sports shirts, long-sleeved polos, and short-sleeved button-ups. They were not really popularized until the end of the classic menswear period, but they still count as vintage.

And if they work for two James Bonds, who are we to say that it won’t work for you.

James Bond Style Rules – Menswear Secrets from 007

Black Shirt Cons

1. Black Is Hard to Maintain

We’re familiar with many great laundry hacks, but none hold the secret to having black shirts look immaculate after numerous washes. If you’re washing your black shirt, you’ll start to see it fade fairly quickly. The luster of deep black will be lost and your shirt will look tired and dull.

Damage is caused by dye deterioration and from friction to the fibers themselves. This kind of damage cannot be avoided when you’re constantly washing and wearing these black shirts. At best, you can mitigate the damage through hand washing or minimal machine washing. And even if you decide to re-dye your black shirts at home, they just never look as good as when they were brand new.

One of Preston's laundry hacks is using dryer balls to keep his clothes soft. Here, he shows dryer balls made of aluminum foil and rubber.
One of Preston’s laundry hacks is using dryer balls to keep his clothes soft. Here, he shows dryer balls made of aluminum foil and rubber.

What does this mean for you? It takes considerable time and effort to keep your black shirts black.

2. Black Shirts Are Easily Marred

Why is this damage from washing such an issue? Because black shirts show discoloration very prominently.

Deodorant stains are perhaps the best-known culprit, but any kind of food or drink residue, dust or pollen from outside, frayed bruised or torn fibers, and any discoloration that isn’t very dark – these will all be very obvious on a black shirt.

A discolored black shirt [Image Credit: ThriftyFun]
A discolored black shirt [Image Credit: ThriftyFun]

Even dark stains can appear on a black shirt because of how they catch the light relative to the rest of the garment.

3. Black Shirts Are Hard to Combine

Remember when we said black shirts were considered versatile? This is true in the sense that black won’t clash with most colors, but that doesn’t mean that black will comfortably pair with just about anything. Black interacts dramatically with other colors.

This is sometimes a good thing – like in formal attire with high contrast against other elements of the outfit – but it’s often a bad thing – when a black shirt makes other colors appear loud and distracting or muted and dull.

This issue is especially apparent with pairings like navy and black, which looks muddy and indistinguishable, burgundy in black, which is giving us strong “lounge lizard” vibes, or a brighter red and black, which looks a bit too much like a cartoonish representation of the devil.

Also, black is a common color in outerwear, and overloading a black shirt with a black leather jacket creates a monochromatic look that can appear flat and uninspired.

Monochromatic Outfits: Should A Gentleman Wear Just One Color?

4. Matching All Elements of Black is Hard

Contrary to what you might assume, there are a multitude of shades of black. If you’re wearing a black shirt and any other article of your ensemble is black, the slight variation between the shades of black will be immediately noticed and is quite distracting, but it is also intrinsic to black dyed fabric.

Unless the two articles are made from the exact same material, using the same dye, there will be a difference in shades. Evening wear is always cut from the same cloth precisely to avoid this jarring contrast.

Evening wear uses the same black fabric to ensure the exact shades of black overall
Evening wear uses the same black fabric to ensure the exact shade of black overall

5. It’s Everywhere

Because they are believed to be flattering, mysterious, and easy to pair, black shirts have become a mainstay in men’s fashion. You’ll see them regularly on the red carpet, strutting down haute couture catwalks, and seemingly in every nightclub, bar, and lounge.

If you want to use your clothes to express your own personality and sense of style, it’s usually best to avoid the trends everyone else is chasing, especially when those trends do so much to make everyone look the same.

Wearing Black T-Shirt The Classic Style

That we’ve considered the pros and cons, let’s take a look at a few tips so that you can incorporate some with classic style.

Consider Contrast and Complement

Black is a bold noticeable color. To balance it out, consider contrasting it with equally bold, but complementary colors. Remember to avoid distracting color combinations like the ones we mentioned earlier.

Raphael in a high contrast black and white look
Raphael in a high contrast black and white look

What colors will work with black? Salmon, most shades of light to medium gray for a stylish monochromatic look, earthy greens, cool blues, both shades of light to medium brown. The general advice against mixing black and brown is usually referring to black or brown leathers. Tan and other light earth tones, and shades of white, including off-white. The high contrast black and white look is very bold and will garner a lot of attention. It’s important to keep that in mind. Keeping all eyes on him was clearly what Raphael was up to in this photo.

Find the Subtle Sweet-Spot

If you’re not one for bold color combinations, it is possible to pair black shirts with other dark colors. But, it takes skill. You have to ensure that there’s sufficient contrast to ensure that the ensemble does not look like a mismatch of very shades of black, which can be an extremely fine line to walk.

Black usually pairs well with shades of dark green [Image Credit: The Adult Man]
Black usually pairs well with shades of dark green [Image Credit: The Adult Man]

In general, if you have any concern that a combination lacks contrast, you’re probably correct. In this case, take some time to figure out how to add more distinction.

Pick a Punchy Pattern or Atypical Texture

A great way to ensure that your black shirt stands out from the rest of your ensemble is to pair it with a bold pattern or different texture. That’s what I did for our 1 million subscriber livestream; pairing my black shirt with a black and cream, checked, double-breasted jacket. A black and cream contrast helped the black shirt to pop wonderfully. The cream in the jacket balanced out the black and the shirt and kept it in check.

These patterns work well with high-contrast looks because they add visual interest that balances the black. The patterns also work well when pairing with other dark colors; by clearly differentiating the black elements from the rest of the outfit.

Kyle wears a check-patterned jacket with his black dress shirt
Kyle wears a check-patterned jacket with his black dress shirt

Texture provides a similar distinction. It’s one of the reasons why both light and dark wash denim jeans pair well with black.

Keep It Casual

Black is always associated with formal wear. So, this can make a jarring when worn with any outfit that is closely associated with both day or evening wear, but isn’t technically formal wear. 

Essentially, the presence of the more formal black spoils the intended casual look of business casual or semi-formal. Preserving your black shirt for obviously casual occasions will ensure that you don’t run into that weird middle ground of “casual but also formal.” This will also give you the opportunity to roll up your sleeves or wear short sleeves.

For the added contrast and warmth of your skin tone, there’s a lot to offset the austerity of a black shirt. Also, casual shirts will give you more opportunity to savor wear and tear. A lived-in black shirt will develop minor fraying and damage, which shows contrast and distinction.

A  black cotton sport shirt is best for a casual look [Image Credit: Neiman Marcus]
A black cotton sport shirt is best for a casual look [Image Credit: Neiman Marcus]

This will ironically make the shirt look more appealing as the subtle variations in color will give the shirt depth and prevent it from looking like a black hole sucking all of the colors out of the cosmos.

Because the shirt is worn casually, you don’t need to worry about appearing unkempt or slumpy. In fact, this elegantly casual approach can add an element of sprezzatura flair to any outfit and ensure the longevity of your casual black shirts.

What Exactly is Sprezzatura?

Toss the Tie

Generally speaking, neckwear rarely works well with black shirts. They either blend in too much or stand out with too much pop. Neckwear and black shirts are almost seen exclusively as part of strict monochromatic looks, which are definitely not a component of classic style.

We do think that the monochromatic look can work within classic style, but requires the use of various color shades, which cannot be done with black – unless you feel very confident distinguishing the differences between onyx, wrought iron, and soot.

Preston in shades of blue matched with a charcoal gray cardigan for a monochromatic look
Preston in shades of blue matched with a charcoal gray cardigan for a monochromatic look

In keeping with the casual nature of black shirts, we recommend that you skip the tie to ensure that you have no awkward color clashes and to dress down the formality of black.

Follow Formality 

Speaking of formality, you’ll have gathered from the examples previously mentioned that a black shirt is typically worn as part of a Black Tie ensemble. Suffice it to say, we’re not exactly fans of this look.

For occasions that call for Black Tie, you shouldn’t be wearing a black dress shirt. It just isn’t part of the established dress code. For Black Tie-adjacent dress codes like alternative Black Tie or creative Black Tie, you could technically wear a black dress shirt. But for the reasons we’ve outlined in this post, we don’t think that it will bring out your greatest potential in formal events.

Wearing a black dress shirt for Black Tie is not appropriate for the dress code
Wearing a black dress shirt for Black Tie is not appropriate for the dress code

Conclusion

We hope that we have given you the information you need to help you decide if you should be wearing a black shirt.

In most cases, a black shirt is a missed opportunity to take advantage of many of the other great colors you could be wearing. But, every now and again, a black shirt can be an interesting change and it’s something that I, at least, like to occasionally indulge in – like in the outfit I’m wearing today.

Outfit Rundown

Kyle's stylish but still classic take on wearing a black dress shirt (Pictured: Finest Socks In The World - Over The Calf in Black Silk from Fort Belvedere)
Kyle’s stylish but still classic take on wearing a black dress shirt (Pictured: Finest Socks In The World – Over The Calf in Black Silk from Fort Belvedere)

Today, I’m wearing, again, the cream and black checked, double-breasted, jacket from Hugo Boss. I’m pairing that with a casual, short sleeve –  kind of a stretch material – black shirt from 7Diamonds. Really comfortable. One of my favorites. So, it’s heavily worn with some black trousers and black dress shoes and the black formal socks from Fort Belvedere.

Check out the Fort Belvedere shop for socks like these.

How do you wear a black shirt in the classic style? Let us know in the comments!

Kyle Thibodeaux

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