Yes there’s a right way to do it and no it does not involve a polo shirt. Have you ever wondered why shirts even come with collars? They feel restrictive. They’re superfluous fabric. It’s an extra thing to iron. It seems like we’d be better off not having to wear them. The thing about the collar though is that it does exactly what good clothing is supposed to do – draw attention to the features of the person wearing them.

A collar is like the frame of a picture – without one it looks unfinished. Too much and it overpowers the picture by drawing focus to the frame itself. A good collar and a good frame enhance the appearance of what they’re framing without drawing any attention to themselves.

What’s the first thing you see when you look at this guy?

Everything about this is wrong. But the collar is the first thing to jump out at you. It takes a minute to see him.

Contrast that with these two.

Crisp shirts with collars that frame perfectly. Being a movie star helps but you get the point.

Just wearing a button-up shirt won’t do that for you though. Unless you prop up your collar the correct way, it’ll get lost underneath your jacket like this.

Enter the collar stay. These are little pieces of plastic you slide in your collar to keep it from hiding under or popping in front of your jacket lapel when you’re tieless, or from having the tips of your collar roll up when you’re wearing a tie.

You can find little jars like this in almost any clothing store. I found mine at Brooks Brothers but have seen them at places like J Crew and Banana Republic. Mine came with about 15 pairs in three different sizes and cost me less than five bucks. These are what you want to wear any time you have a tie on and do a decent job of keeping your collar sharp when you don’t have a tie, but they’re not quite as good as what you see on the Ocean’s gentlemen.

For that you have to make a bit more of an investment. It’s more than worth it though. In fact, I’m working on a post that includes the top 25 essentials any man should have in his wardrobe and these are one of them.

They’re called Wurkin Stiffs and essentially they’re metal collar stays with a powerful magnet you use to keep them attached where you want on your shirt. The price is a bit daunting. If I remember right, I paid about $25 for mine and got them at Nordstrom Rack but they’ve been worth every penny. It’s the small and subtle things that can really set you apart and these are a great way to step up your style game. And remember to keep that second button undone.

* I have not been offered anything from Wurkin Stiffs to endorse their product. They don’t even know I exist.