1. White pocket square or handkerchief

The size isn’t really important. I usually like it a little bit smaller because it’s not going to puff off. The easiest to wear pocket square is the one that is always elegant. It’s not only the most casual, but also the most formal depending on what you pair it with.

2. Herringbone pattern

It’s made from silk. The fact that it’s made from silk makes it a bit dressier. The key here is that we’re using solid colors, very easy to match, although you want to make sure it goes with something that you’re wearing.

3. Paisley Pattern

My favorite pocket squares are the ones with complicated patterns that you don’t normally see in men’s clothing. The great part about that is that you could have a striped shirt. You could have a solid jacket. You could have a patterned tie, a polka dot tie, and you can still wear it is a paisley. A wide variety of colors that you can find something that goes with another item in your outfit.

4. Striped Pattern

The hardest pocket squares to match in my opinion and the ones I wear the least often are stripes.Part of that is because if you’re already wearing a striped pattern, let’s say a shirt, then you’re kind of doing a double repeat pattern in addition to the stripe in the pocket.

It’s just harder to pull off perhaps because the lines just going along in its curving, so I try to stay away from these types of pocket squares. If you’re looking to start off, go with a simple white, easily the most simple and classic. You’re never going to go wrong with the simple white.

Pocket Square Style and Small Details

I just had a great interview with David Siteman Garland over at The Rise to the Top. At the beginning of the interview, I pointed out that the whole reason he first popped up on my radar was when I was looking for a podcast to start listening to. He was the only guy I saw that actually dressed really sharp.

He was in a jacket and he had a pocket square. When I saw that, I was like, “You know, this is a guy that pays attention to the details,” It turned out that he had done an internship with FHM Magazine, so he understood a bit about men’s style.

If any of you guys are into automobiles or motorcycles, whenever you see a guy in a bike and if you can really talk that type of language. You can go in and form a much deeper connection because you know the details. You know everything that goes into it, and it’s like that way with style.

I highly advise that you always look at the way other people are and you can pay attention.

When you start paying attention to style as a man, you’ll start to notice other women as well and it’s a great way to start a conversation when you can make a very detailed comment about something that she’s wearing and really show an interest in her and make the conversation about her. Everyone likes to talk about themselves.

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