10 Types of Stylish Men – Which One Are You?

10 Types of Stylish Men – Which One Are You?

Want to know how to WASTE money?

Go out and try to be stylish – without knowing what TYPE of stylish man you are. Knowing your style isn’t just knowing what you want to wear…it’s knowing why you want to wear it.

Each of these ten types of stylish man has a different relationship with style… which one are you?

1. The Jet-Setter


This guy wants function, fashion, and comfort in one package. So the jet-setter is willing to pay quite a bit more for his clothing. He wants clothing that’s going to perform.

For example, when he buys a jacket he’ll go with 100% wool. He wants the insulating properties and the durability of wool, and he wants something that’ll look great and have a great drape when he gets off that airplane, because he’s a frequent flyer.

Because he travels to a lot of different places and meets a lot of new people, he knows people are going to make a snap judgment, so he dresses sharp. He realizes that clothing sends a message.

He’s willing to pay a premium to get fashion + function + comfort.

2. The Dandy


The Dandy is a man who has the courage to dress for himself. This stylish man really does care about the clothing. He cares about all the craftsmanship that goes into it – he wants to know which artisan actually made his shoes or his boutonniere, and he’s willing to pay a premium for that attention to detail.

To understand historically where dandies come from, look at a guy like Oscar Wilde. Here’s an Irish poet who made his way into British society and led a style revolution.

That’s why I respect dandies – they dress for themselves and use clothing to get what they want.

3. The Rugged Man

A rugged man’s clothing is practical, hard-wearing, and masculine. It’s made to be functional – to actually stand up to manual labor.

For example, if you look at a pair of work boots, you’ll see they have a rubber sole. Why? Because if you’re out there working on cars and the oil gets spilled, you don’t want to slip, you want something that’ll give you traction.

Then if you look at the upper you’ll see it’s a thicker, heavier leather than a dress boot. You know you could splash mud on it or go into water and it’ll be fine. On a good work boot you’ll also see a Goodyear welt to increase water resistance and allow it to be resoled.

4. The Rebel, A.K.A. The Rockstar


This guy is incredibly confident, he’s unconventional, and he’s not afraid of attention. Many of us picture the ideal rebel as the guy with a leather jacket, white shirt, blue jeans, and boots – but that’s just one vision.

I think any guy who isn’t afraid to dress to stand apart, who knows who he is and just dresses that way, is a rebel.

If you want to be a true rock star then you’ve got to have confidence. You’ve got to practice wearing the clothes at home so you can confidently go out in them, because sometimes you will draw attention. So you need to be able to stick to your guns and know what you stand for.

5. The Classic Style Guy


The clothing in this man’s wardrobe is all about being timeless. It’s about quality. It’s about proven pieces that are not going to go out of style.

When a man wears classic clothes he knows he’ll be able to look at a picture of himself ten years from now and it’ll still look great.

Because of this, he knows he can make an investment in quality pieces. He’s willing to spend hundreds of dollars on a pair of shoes, thousands on a suit, because he’s going to get a lot of wear out of it.

This stylish man is not to be confused with retro dressers, who wear vintage styles from, say, the 1950s. That’s very different. I have NOTHING against vintage guys – but the classic dresser simply wants to wear clothing that’s never going to go out of style.

6. The Fashionisto


This guy is all about adopting trends and going with the right brand at the right time. He’s going into all the fashion magazines, he’s following the runways, he knows what is going to be hot this season. And he knows that he’s taking a risk.

The clothes a fashionisto buys could be out of style in a year.

But he’s willing to risk that to be the first one to stand out wearing it. He wants to be on the bleeding edge of fashion.

7. The Street Style Guy


Surprisingly similar to the fashionisto, this guy is very into brands, but he isn’t necessarily following trends. He looks to lead fashion by MAKING trends and to send signals of success with his image. He wants an audience and he realizes that the street is the modern-day runway.

The street style guy is a risk-taker who pushes the envelope and goes bold with color and casual style.

He experiments in real time by throwing different pieces together to create his own style and seeing how his audience reacts. Street style has a powerful influence thanks to The Sartorialist and similar photography sites.

8. The Uniform Man


Here we have a strategic dresser who’s clear with his message and very calculated. He’s spent a lot of time up front developing his uniform, crafting his look, and then he’s set it on cruise control.

A uniform doesn’t have to be a suit or a sports jacket. It could be very casual clothing, such as Mark Zuckerberg’s uniform of a gray t-shirt, gray hoodie, and jeans.

The uniform guy doesn’t want to think when he puts his clothing on. He’s often very driven and wants to focus in on other things, like building a business or growing a nonprofit.

He realizes his clothing needs to send a message – and when it sends the message he wants to send, he puts it on endless repeat.

9. The Preppy Guy


Preppy style is all about tradition and society. It’s about wearing brands and pieces of clothing that signal, ‘I’m part of the group.’

A lot of people see this as negative – ‘Those people are elitist.’ And I agree – in some cases, they are.

However, there are some groups where identifying yourself as a member makes a lot of sense – for example, if you’ve served in the military, regimental neckties allow you to identify that someone was part of your military unit.

Another example is the Masons. They wear certain things that send a coded signal to those in the know – ‘Hey, I’m somebody that you want to get to know, because we’ve got something in common.’

10. The Playboy


This isn’t really about play. It’s about power, social status, and using them to generate attraction.

So for the playboy, when he walks into any situation, he wants to come off as the alpha – as the man that’s in charge. If you come off as in charge, if people are calling you sir, you look like you’re in a position of power even if you’re not. You have high social status – which means you’ll be perceived as more attractive, both to men and especially to women.

So now the question is – which one of these stylish men are you?

1. The Jet-Setter
2. The Dandy
3. The Rugged Man
4. The Rebel, A.K.A. The Rockstar
5. The Classic Style Guy
6. The Fashionista
7. The Street Style Guy
8. The Uniform Man
9. The Preppy Man
10. The Playboy

Are you a mix of two or three types of stylish man? Do you think you’re one type, but want to be another? What steps can you take to become the type of stylish man YOU want to be?

This article was brought to you by Thursday Boots.

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