10 Types Of Stylish Man – Which One Are You?


Being a stylish man is more than what clothes you wear. It is an attitude, a personality. It is the outward expression of who you are.

There are 10 types of stylish men and if you don’t know who you are, you can kill your confidence.

Stylish Man in Suit

If you are outgoing and trendy but are dressing conservatively, then you can feel stuffy and hidden. If you are conservative and classic but are wearing flashy clothing, then you can feel garish and unprofessional.

In this article, I lay out the 10 different types of stylish men:

  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

Each of these types of stylish men has a different relationship with style; which one are you?

Stylish Man Look #1 The Jet-Setter

Man in Suit on A Jet

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 an excellent drape when he gets off that airplane because he’s a frequent flyer.

Because he travels to a lot of different places and meets many 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.

Stylish Man Look #2 The Dandy

Man In Beige Suit

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

Out of all types of stylish men, this is the man that will be able to answer questions about different garments or trends.

Stylish Man Look #3 The Rugged Man

Rugged Man in Woods

A rugged man’s clothing is practical, hardwearing, and masculine. It’s functional – to stand up to manual labor. This is the blue-collar worker, the soldier, the cop, and the fireman. They fix your car, save lives, and protect your city. Their clothes need to stand up to all of that.

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.

Stylish Man Look #4 The Rebel, A.K.A. The Rockstar

an attractive guy on a motorbike with a woman

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 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.

Stylish Man Look #5 The Classic Style Guy

Man in Suit

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 invest 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 a retro dresser who wears vintage styles from, say, the 1950s. That’s very different. I have NOTHING against vintage guys – but the classic dresser wants to wear clothing that will never go out of style.

Stylish Man Look #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 will be hot this season. And he knows that he’s taking a risk.

The clothes a fashionista 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.

Stylish Man Look #7 The Street Style Guy

Casual Street Style

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 style and seeing how his audience reacts. Street style has a powerful influence thanks to The Sartorialist and similar photography sites.

Stylish Man Look #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 upfront 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 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.

Stylish Man Look #9 The Preppy Guy

Preppy Guy

The 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.’

Stylish Man Look #10 The Playboy


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

When he walks into any situation for the playboy, he wants to come off as the alpha – as the man that’s in charge. If you come off as in charge, if people call 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 look more attractive, both to men and especially to women.

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

Are you a mix of two or three types of stylish men? 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?

  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


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