Thinking about getting a black dress shirt? Here’s why you should think again.
Black dress shirts — despite seeing them all the time on the red carpet, they rarely look good out in the “real world.”
There is so much to consider when wearing a black dress shirt — your skin tone, your pants and jacket color, your accessories, and more.
Today I’ll explain why black dress shirts are popular in Hollywood, argue why they’re so hard to pull off well, and provide alternatives to help you look your best. I’ll conclude with an alternative opinion on black dress shirts from a professional stylist.
Why Are Black Dress Shirts Popular in Hollywood?
I most often see black dress shirts worn as part of an all-black look.
All-black has been trending in Hollywood. Alan Au, celebrity stylist and co-owner of Jimmy Au’s For Men 5’8″ and Under, explains why:
“All black happens a lot in L.A. — Hollywood, actors, and musicians. I get items specially made in black in lightweight fabrics, or monochromatic with black and charcoal. The natural dark color for summer for most of the US is navy blue. However, this past spring, dark gray or charcoal was trending, along with black. John Wick 4 definitely affected black suit sales.
Black on black has always been seen as cool and mysterious, and dangerous. [It’s also long been the color worn by film] crews and waitstaff… For everybody else, midnight blue, dark brown, or dark gray makes a better ‘black’.”
Alan went on to explain that one reason people in the film industry often wear black is that if you’re allowed or note allowed to hang out on set, you don’t want to be seen — hence all the black backstage.
I think that perhaps it is due to the prevalence of black in the film industry that so many actors attempt to pull off black dress shirts.
Why Black Dress Shirts Are Rarely (if Ever) the Best Choice
The thing is, black dress shirts are very difficult to wear well. I think they can have their place, but there is almost always a better alternative.
Using Tom Cruise as a case study, I’m going to try and demonstrate my point. (Check out this article for more info about Tom Cruise’s style).
However, before sharing my first example, I want to acknowledge that in this article I share a lot of side-by-side photos of celebrities. Since the photos I was able to find in the public domain span across time with many different occasions, facial expressions, and lighting scenarios, it can be difficult to compare outfits accurately. Just keep that in mind as you continue reading.
To begin with, here’s a photo of Tom Cruise wearing a black dress shirt:
You’re probably thinking, “Not too bad!”
I must admit that Cruise can look good in a black dress shirt work, but he is Tom Cruise (and you’re not 😁).
The black shirt looks ok in the photo above in part because the dark grey suit is close in color.
Another reason is that movie stars tend to look good in anything — Tom Cruise could probably wear a burlap bag and still look stellar.
Here’s a more recent example of the actor wearing a dark blue dress shirt.
While it works, I still think that a lighter-colored shirt would’ve been better here. You can see that his light skin looks a bit washed out in contrast to the black shirt.
That said, my friend Alan Au doesn’t agree with me on this point. He says that most stylists would disagree with me here, as the shirt actually helps brings out his high-contrasting darker features like his hair and eyebrows.
Speaking of which, people with darker skin tones avoid looking washed out and can more effortlessly nail looks that incorporate the black dress shirt:
That said, I’d argue that most of the time (if not always) a white dress shirt is a better option than black, even for people of color.
Dress shirts, differing from casual button-downs, are worn in more formal situations. Consequently, the contrast that a white dress shirt provides lends itself to more formal situations. Besides that, a white dress is much easier to layer.
Another reason a white dress shirt is more versatile is because, as a general rule, your inner layer should be lighter than your outer layer. With black, you can’t really go any darker, and a black-over-black look can be quite ominous.
Finally, poor-quality black fabrics tend to look dull and cheap, especially after being washed. I’ve found this is particularly the case with more formal clothing. So, if you have an inferior quality dress shirt you probably won’t look very good whereas a cheap white dress shirt can often pass muster.
On the other hand, with the right accessories, fantastically fitting clothing cut from quality fabrics, and a little bit of swagger in your step, black dress shirts can look pretty sharp.
5 Alternatives to the Black Dress Shirt
What should you wear instead of the hard-to-execute black dress shirt? Here are five alternatives, using Tom Cruise as an example:
The White Dress Shirt
What do you notice about Tom Cruise’s look in this photo?
Black shirt, black tie, bold sunglasses, and a shiny black suit — together it’s all a little… intense.
Here’s Tom Crusie wearing a similar outfit, except with a few small changes:
Instant improvement, right?
It’s not just that he’s wearing a white shirt — can you spot the other differences?
He’s wearing a dark, conservative-colored suit instead of black that fits well in the shoulders. The suit appears to be charcoal grey which, in my opinion, works better with his skin tone.
Also, he’s wearing a tie in a dark, conservative blue.
Together, the dark suit, muted tie, and white dress shirt lend to a monochromatic appearance overall, without going overboard.
The Dark-Colored Turtleneck
Sometimes you don’t want to look as conservative and traditional as you do while wearing a classic business suit.
Instead of wearing a black dress shirt, consider opting for a turtleneck in black, navy, or dark grey.
Turtlenecks lend themselves to a sleek upscale feel. While they can certainly be worn with suits (particularly navy and grey ones), they’re even more at home with a more casual jacket:
Wear a turtleneck as part of a dark monochromatic ensemble and you’ll be looking sharp and sophisticated.
The Grey Dress Shirt
If you do choose to wear a black suit with dark accessories and want to stand out, choose a grey dress shirt instead of black.
Here Mr. Cruise is wearing a black suit, a black v-neck sweater, and a black tie. He tempers the monotony with a quality medium-grey dress shirt.
It really helps that the shirt has a nice collar. Also, I think that the black sweater and tie are a good choice here.
Grey dress shirts don’t always work, though:
There are two main issues here — the tie is too close to the color of the shirt and the velvet vest is too formal for a grey dress shirt (grey being a less formal shirt color). Since it looks like this was a formal event, a white dress shirt would be a much better choice:
While his pants need hemming and he’d do well to wear a bow tie instead of a long necktie with such a formal tuxedo, you can see that a white dress shirt and a proper tux are vastly superior to a peaked lapel suit with a grey dress shirt.
Now for a side-by-side comparison of an all-black outfit next to an almost identical outfit but with a grey dress shirt:
Ignoring the fit of these suits (you’d think they could afford to get their pants hemmed!), Tom Cruise with his grey shirt clearly looks better than Ben Stiller with his black shirt.
The Light-Colored Casual Button-Up
A black dress shirt can pass while wearing a dark suit, but without a jacket, it just looks off.
A lighter-colored casual shirt is a smarter choice:
That said, grey casual button-ups can work, especially if it has casual elements such as a textured fabric and a button-down color:
Another good option in casual scenarios in which you might be tempted to wear a black dress shirt would be to wear a black turtleneck without a jacket or a black long-sleeve polo.
The Black Tee
Another great casual yet stylish option is to wear a black tee shirt in lieu of a dress shirt.
I wouldn’t wear a black tee with a tailored jacket, but it looks great with a black bomber or leather jacket:
Above, he is wearing a navy suit and navy shirt.
Comparing the two photos above, you can see that these are very similar looks with different silhouettes. The black bomber paired with a tee is a bit more casual but looks more athletic.
Honestly, if you’re going to wear a black shirt, I’d recommend dialing down the formality, and a bomber jacket/tee shirt combo is a great way to look sharp while at the same time staying dark and mysterious.
An Alernate Opinion: Black Dress Shirts Have Their Place
While, as you can tell, I’m personally not a fan of black dress shirts, my friend Alan Au has a more accepting opinion.
Here’s his take:
“Overall, I think black dress shirts have their place. It’s beyond slimming, it makes your body disappear. As far as gray goes, it depends on the person’s complexion and hair color. I don’t agree as a blanket statement, gray is better than black.
Black is trending again and wearing it uniquely includes wearing it with dark gray, navy or dark brown suits with complementing ties. If your goal doesn’t include being mysterious or dangerous, then a black dress shirt should be a pass. To me, the bigger issue is properly pulling off an all black outfit with a black shirt.
A good black shirt is great for hiding in dark corners of clubs and bars. Black can make you shapeless, if that’s your goal.”
Like many (if not most) style-related topics, you’re going to have differing opinions when it comes to black dress shirts.
Final Thoughts
Dress shirts come in all different colors and styles. With all of the options available, I’d be hard-pressed to think of a situation in which a black dress shirt would be my first choice.
Other colors such as white and light blue are much easier to wear, at least for me.
If you want to stick to a completely dark color palette, I’d argue that a grey dress shirt would be a much better choice than black.
However, according to Alan Au’s expert opinion, if you have higher-contrasting features, a black dress shirt may be a good option.
Another option for black-everything looks is to avoid black suits altogether and instead lower the formality and wear black tees, polos, turtlenecks, and casual jackets.
What do you think about black dress shirts? Do you disagree with my opinions? If so, let me know why in the comments!
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