I see a lot of stuff on the internet about how men should use accessories like necklaces, bracelets, or rings to enhance their outfits.

These sources say that accessories are often an easy way to upgrade your style game.

I don’t disagree with any of that. But I think that content around how and why men should wear accessories misses the mark.

I usually find that advice around wearing accessories comes from a purely aesthetic perspective, as in: you should wear this thing in this way in order to look good.

But accessories kind of play their own style game. And that’s what makes them so nice to wear.

Here are the two main things you need to keep in mind when wearing accessories…

Meaning and quality.

Let me explain…

If you are going to wear something like a necklace or a ring, you should make sure it has some sort of importance to you. Most men would scoff at wearing gold jewelry… except when it comes to their wedding ring. That’s because something like a wedding ring has obvious importance to the wearer.

That importance makes the piece “work”.

But it doesn’t just have to be a wedding ring. Anything of sentimental value can be worn authentically and stylishly.

It could be a gift from your wife, or a piece you picked up while on a great vacation. Maybe it’s a family heirloom.

Something that’s special to you and fills your heart with warmth when you look at it will always feel comfortable and natural to wear. Without that specialness, accessories tend to look like affectations.

And that’s why I struggle with how so much content around accessories focuses on simply how they look. An accessory that has real meaning to the wearer doesn’t really HAVE to “look good” with the rest of their outfit.

And that’s what I meant earlier about accessories playing their own game. You shouldn’t need to figure out a way to shoehorn an accessory into an outfit. If it’s special to you, you’ll just wear the thing. Might it clash with other parts of what you’re wearing? Maybe. But again, the ease that comes from wearing something special will translate to the rest of your outfit and make the whole thing seem cohesive.

What about quality? That was the other half of the two most important things to consider when wearing accessories.

Shouldn’t quality not matter if the item in question has meaning, though?

You’re sort of on the right track.

Meaning and quality are related when it comes to accessories. If you have something, say a bracelet, that has a lot of meaning to you, then the quality can be relatively low and it won’t matter too much. However, if the piece has very little meaning, then the quality of that piece needs to be higher.

Here’s an example…

A friendship bracelet made out of yarn that your kid made for you for Father’s Day has a TON of meaning, but is of very low quality. You could definitely wear that.

A plastic bracelet you bought in the mall on a whim has no meaning AND is of low quality. I would advise against wearing something like that.

On the flip side, a bracelet made of a precious metal that you bought on a whim could absolutely be worn stylishly given its quality.

Do you see what I mean with all of this?

Let me put it more bluntly…

If you’re going to wear something cheap, make sure it has some sentimental value, otherwise it will look bad.

Now, some people consider watches accessories, but since watches have an actual function (as opposed to something like a necklace which is purely ornamental), I put them in their own separate category. A guy can’t be faulted for wearing a cheap watch that has no meaning to him if it keeps good time and helps him navigate his day. That’s more of a tool than an accessory.

They way I like to think about accessories is that they don’t really need to “look good”. They don’t have to play well with other elements of your outfit. They don’t have to match formality levels with anything else.

Within reason, a sentimental piece or a high-quality piece will pretty much always work with what you’re wearing.

Personally, I wear two accessories every day. One is my wedding ring and the other is a necklace. My wedding ring obviously has special meaning. My necklace is a thin metal chain with two items hanging from it: an old Irish coin and a small pendant with St. Patrick on it that my mother gave me. I have been wearing this necklace for over 20 years.

Keep in mind, though, that with accessories, you’ll still need to exercise some restraint and common sense when wearing them. They should be small, almost imperceptible little add-ons, not the main focal point of your appearance. You shouldn’t look like Johnny Depp with arm-fulls of bracelets, for example.

My necklace sits unseen under my shirt so I can wear it with everything from a t-shirt to a tuxedo.

Any accessory should kind of be a part of you instead of a part of your outfit. As men, we are naturally swimming against the cultural current when it comes to stuff like this. Women can much more easily throw something on just because they think it looks nice. Like it or not, we men need to have a little more substance behind stuff like jewelry or other little bits of flourish.

I don’t look at that as a bad thing, though. Like I said, as long as an accessory has meaning or is of good quality, you don’t need to coordinate it with your outfit as much as you would, say, a necktie or pocket square.

That allows for a lot of freedom. I actually think that’s a great way to look at a lot of menswear. Sure, there are “rules” and “guidelines” for how things should be put together. You can either look at those as restrictions, or as sandboxes for experimentation and fun.