The first rule with a black shirt is you need to have the complexion for it. Any man can wear a black shirt, but only men with dark hair and anywhere from medium to darker colored skin are really going to pull it off.

I’ll talk in part two about other men who wear it and what they wear it for even though it doesn’t complement them the best, but it’s going to be the dark-haired, dark-skinned man who can wear the color black the best. The reason is it’s not going to have a stark of a contrast and it’s just really not going to overpower his natural colors.

Now, let’s say you have light colored hair and light colored skin, “When can I wear black? Can I even wear black?” Yes, you can when you want to isolate the face. One of the most famous examples is Steve Jobs and his black turtleneck. He’s up on a big stage.

Let’s talk about colored versus uncolored black shirts. Either way, it’s going to send very similar signals, but a color black shirt is always going to be less formal than a white or a light colored dress shirt. So if you’re wearing it with your suit or  sports jacket, it is going to be less formal than a lighter colored jacket, even if it’s solid.

Now, if you’re wearing it without a collar, it could actually still look pretty good especially if it’s a solid black. I’ve pulled this off. The key with wearing it though with any type of jacket is I think there should be a contrast or you should be wearing something black. Some guys like the black on black look and a guy pulled it off amazingly.

I mean, just look at vintage photos or even up until his unfortunate death, Johnny Cash, the man in black. He was a great example of a man that pulled this off. Here’s a guy that played in Folsom Prison. Actually I can’t remember the rest of the other prisons he played at but I know he did the Folsom Prison.

This is the kind of guy that is going into prisons and playing for a pretty rough crowd, having a great time, but wanting to send a little bit of a message that he is a rebel, that he is outside. I think he even talked about in Nashville at the time a lot of people were wearing lighter colors. Here’s a guy that shows up in just dark colors and trying to create a bit of mystery and he did a great job pulling it off.

I’ve seen this overdone though a lot of times. If you’ve got a very light-colored face, it’s just going to make your head really stand out, so you want to be careful with that look. You need to be a little bit more style advanced. If you’re going to try to introduce a black shirt, I think you should go for something that is matching it with something that’s clearly not black.

What do I mean by that? I mean don’t try to match it with a navy suit because it’s close enough that some people may wonder, “Well, does he know that they’re different colors?” Instead, go for a light tan or  a sports jacket that is white and black.

So clearly you can see that this does not match exactly, but there’s enough of a contrast. And if you’re going in the same color scheme, you could mix it with greys, so black shirt with grey trousers or grey jacket. That is better than trying to go with anything in the navy.

You can go with charcoal and that’s an okay look, but I like it whenever the grey is lighter because again, we’re going to see a little bit of the contrast between the fabrics. Again, to get it too close and it’s not exactly close, that’s when it starts to look bad.

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