Style Guide: How to Wear a Black Shirt

Lester Fangonilo - October 5, 2021


There is a certain mystique that men dressed in plain black shirts have: they look sophisticated and elegant, yet have a certain ruggedness and a devil-may-care attitude. 

A man in a black shirt may fit into a genteel gathering, but he stands out - especially if he wears that shirt well - and because of his cool demeanor and the way he abides by his own rules. Look at how legends like Johnny Cash have made it their signature article of clothing or the way rock bands like Metallica have practically made black tees a uniform.

But we have to ask: is there a right way - and, conversely, a wrong way - to wear a black shirt? Well, to be honest, it depends on the type of shirt and, as always, the attitude of the man wearing it.

In this feature, we will specifically present ways by which to style a black dress shirt as well as black t-shirts.

Styling the Black Dress Shirt

To be frank, there is just one key rule to wearing a black dress shirt - and that is to keep it simple; everything else is all about the details. In which case, here are some practical tips when it comes to styling this impeccable piece of clothing:

Black with Black = Perfect   

Black shirts go beautifully with other pieces of clothing in the same color. You can wear it under a black blazer or a tailored trench; wear it over a pair of elegant slacks or sleek black denim. Of course, black shoes are always a must to complete the outfit for the perfect sense of dark elegance.

Black with Dark Colors = Thanks, But No Thanks  

What are you, a cartoon character or a villain out of the old Dick Tracy comic strips? Pairing black dress shirts with dark shades of red, blue, brown, and even green will result in a look that is comical, even cartoonish in appearance, giving the wearer a somewhat juvenile vibe - definitely not the look you want in good company. 

Dark Denim is Sexy   

Deep navy - almost indigo - denim seems to have been made to pair with black dress shirts. While black denim has its charms, wearing a black dress shirt with the darkest blue jeans exudes sex appeal in spades. Easy to throw on - and even easier to get away with - it's an outfit that works well for casual Fridays that segue into a hip night on the town. Wear it tucked in or untucked, it's a combo that's practically impossible to get wrong.

Whatever You Do, DON'T Wear White With It  

Okay: a white dress shirt worn beneath a tuxedo jacket or under a black suit jacket is classic - a black dress shirt accessorized with anything white is an eyesore. Sure, a white tie with a black shirt is something guys wear in the movies. But only if they're Mafiosi or some thug's hired muscle. Unless you're in that line of work (and even modern-day mobsters have more sartorial sense than that), skip it.

The Color of Your Skin Doesn't Matter  

When it comes to black dress shirts, disregard the common misperception that pale-complexioned blonds will look washed out in them. Black dress shirts have a place in any man's wardrobe regardless of his race or skin color; what matters is the confidence and attitude he exudes when wearing one.

Styling the Black T-Shirt

Today, black T-shirts have gone beyond their stereotypical role as the uniform of choice for metalheads and emo kids. In fact, it's very easy to create an elegantly casual look based on a black T-shirt and it would all have to depend on what you wear with it and, more importantly, how it's cut or made.

It All Starts with the Neckline   

Most black tees sport a classic crewneck or round-neck collar, but bolder gents who want to show off a bit of [well-toned] skin around the neck and chest would do well to have a V-necked one in their wardrobe to wear beneath tailored blazers for a spin on rugged chic. Want to get a bit more classy? 

Granddad shirts - the ones with a button placket at the collar - are perfect for a chic layered look in the colder months, looking extra cool beneath a rugged denim or leather jacket or even a preppy cardigan.

Consider the Fit   

The fit is dependent on your personal preference or what you feel comfortable wearing. But there are a few rules to observe: slim-fitting shirts work best with equally slim-fitting bottoms.

Standard sized tees work well with conventionally sized bottoms as well as skinny jeans. Big baggy tees work best with comfy bottoms or track pants, but can also be worn with slim-fits for a modern urban vibe.

Classic Combinations   

While there aren’t really any hard and fast rules regarding what to wear with a black tee, some combinations are just meant to be.  In the spring or fall, wearing a black t-shirt under a dressy blazer or suit jacket adds a rugged masculinity to one’s everyday look at the office. 

Black tees worn over jeans have also transcended the roadie stereotype and can be seen in every season, save perhaps for the height of summer - during which time, black tees with board shorts rule. 

Also, while white tees seem to be de rigueur with leather jackets or bomber jackets, a black t-shirt also has a certain je ne sais quoi when worn in a similar fashion. Aviator sunglasses are, of course, optional.

What About Athleisure?   

The athleisure trend has brought about tapered and fitted joggers - the male spin on leggings - and even the most hard-core fashionistas are hard-pressed to pull off a look with them. But if you pair black, dark blue, or slate grey joggers with a slim-fit black tee, the overall look transcends conventional athleisure and crosses over into urban chic with minimal effort.


Your overall look is only as good as how you carry it. To even boost your confidence, there’s no better way to finish off the look except accessorizing. The black color is perfect and easiest to accessorize.

Depending on what sort of event or vibe you’re going for, wear an accessory piece that makes color leap off your black shirt. For instance, you can wear shoes, belts, watches, bracelets, and a contrasting scarf to really achieve an impressive aesthetic. 

What’s also great about an outfit that revolves around a black shirt is that you can wear any type of shoes. Are you looking for stylish grunge? There are distressed shoes for that. Do you want to look smart and casual? A wide selection of great-looking and colorful sneakers are also available. 

Think of the black shirt as a canvas with which you can make yourself a piece of art. Don’t be held back - accessorize, accessorize, accessorize!

Need Apparel with Attitude? Consider Oliver Cabell

While Oliver Cabell is a brand that has become synonymous with exquisitely crafted leather sneakers, its recent foray into men’s casual clothing brings its signature craftsmanship up a notch. 

Take your outfit up a notch with high-quality shirts paired with accessories such as bracelets, chains, necklaces, and shoes. 

Clothes may make the man, but Oliver Cabell transforms him into a modern man of the world.

The Dos and Don’ts for Wearing Mens Black Dress Shirts

You may think everything works when you’re wearing black, but there are certain rules to follow if you want to use it with style.


  • Pair your black dress shirt with another black piece of clothing, such as shoes, jeans, or slacks. The first rule about black color: it works great with black.  So don’t be shy in pairing a black dress shirt with a black blazer, jeans, or shoes. You can’t go wrong.
  • A black dress shirt needs to be worn with dark denim. Whether tucked or untucked, dark denim goes extremely well with a black dress shirt.
  • For extra boldness, wear your black dress shirt with a dark blazer. Be suave and elegant for the occasion.
  • A black dress shirt knows no skin or hair color. It’s entirely false to suggest that you need to sport only lighter skin or hair to give justice to a black dress shirt look. 


  • Don’t ever wear red, dark green, navy or brown alongside your black dress shirt. If you must go with a dark tone, choose black. 
  • Never pair a black dress shirt with something white. While a white dress shirt works well with black slacks, tie, or suspenders, the opposite isn’t true. You’ll get attention for the wrong reasons.
  • The same goes for a black dress shirt and white accessories - just don’t.