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How to be a More Stylish Man in 2020

How to be a More Stylish Man in 2020

It’s wild to see how much men’s style has transformed over the last decade.

I never thought I would see Wall St. bowing (sorta) to the shift towards the casual style, a sneaker becoming a staple for a timeless wardrobe, or the return of the fanny pack. (Still on the fence about the last one.)

It’s even wilder realizing that I’ve been helping guys improve their style on The Essential Man for half that time. That’s 5 years! If that were a kid he’d be a tiny human with actual opinions!

As we start the new year (and decade), I want to gather up all that I’ve learned working with professional men 1-on-1 with their style to help you answer one crucial question:

How can you enter the 2020s as a modern, stylish, dare I say, essential man? 

A great example of a S.E.L.F. outfit

01. The modern essential man’s style is adaptable

After working with hundreds of men across a dozen different industries – from tech companies like Google, journalists at The New York Times, to a medical lab technician in the South, it’s clear this shift towards a more casual wardrobe isn’t going anywhere.

What IS coming is a new addition to the traditional lineup of dress codes. 

Despite the varied industries, locations, and ages of my styling clients, they all had one thing in common: They were successful men who couldn’t fit into one dress code category. They weren’t casual. They weren’t formal. They were barely even business casual.

They could dress casually at work, but rocking some athleisure track pants and a tee were out of the question.

They had no desire to go full Mad Men daily, but had a few occasions where they needed to go “Boss Mode” and don a sharp suit and perfectly dimpled. 

On the weekends, they wanted to put away the beat-up college tee and dad jeans and have a great, grown-up look that could withstand their 2-year-olds tendencies to toss around their cut-up spaghetti.

In short, men today need the Ethan Hunt of wardrobes: something badass that could handle almost every situation effortlessly.

The modern, essential man is a successful earner whose lifestyle is flexible (S.E.L.F.), and he needs a wardrobe to reflect that. 

Casual on the weekends. Business casual at work. Sharp and professional for those big meetings. Without owning a ton of clothes, and with a unifying, stylish aesthetic!

The great thing, this isn’t some unattainable holy grail of a wardrobe. It’s what I’ve been writing about on The Essential Man for years! 

In 2020, I’ll be sharing more articles and emails on building a unified, versatile wardrobe to handle every situation in your life with style. If you’re new here, I highly recommend checking out a couple of my most popular articles below to give you a head start.

Photo via On Point Fresh

02. He has an appreciation for quality (and will invest in it)

I grew up in the San Francisco Bay Area, and whenever someone learns that the question I immediately get asked is “In-N-Out vs. Shake Shack?”. 

And I always answer, “Shake Shack, no contest.” (I also make sure to scrunch my face to emphasis how much of a no brainer that answer is)

Whenever I share my love for Shake Shack online, you can put good money that an In-N-Out apologists will point out the fact that Shake Shack costs 2x more than In-N-Out. 

And you know what I say to that? 

Exactly. That’s why it’s so much better. 

When you invest a bit more, you get quality. This is true for a burger as it is for a pair of boots.

One of my favorite things to do with my private styling clients is to have them try on well made, high-quality clothes, and then pop into Zara. Why? Because quality must be experienced to be understood.

You could watch Youtube videos on what it’s like to fly first class for months, but it will never compare to actually experiencing what it’s like to fly first class for 8 hours. (Spoiler alert: it’s incredible, and it will ruin flying for you forever.)

This year, I want you to experience how game-changing investing in quality is. 

By the way, investing in quality isn’t always about buying the most expensive version of something. You don’t need to spend first-class ticket prices to get better quality when it comes to your clothes. I’ve always stressed paying for the quality you can afford, and when you move up the success ladder, you can upgrade parts of your wardrobe that you love. 

Hell, my daily t-shirts are $9 Supima tees from Uniqlo! Even though that’s extremely affordable, it’s still a huge upgrade from a $5 Hanes tee. 

To start building a wardrobe with more quality pieces, check out my post: “How much should you pay for clothes?”

Summer Peter in Full Effect

03. He is Unapologetically Himself

If you’ve been a longtime reader, you probably have my style mantras memorized by heart:

Dial-in your fit. Start with a wardrobe filled with quality, timeless essentials. Buy them in core colors.

For a lot of you, this is good enough. 

But for some, you might be wondering, what’s next? 

Some men start working with me after being an avid reader of The Essential Man. Their problem? They’re in a bit of a style rut. They’ve taken my core advice and have a solid wardrobe, but it feels a little…repetitive.

Anyone that’s ever been on a training program to get in shape knows this feeling. It’s the style equivalent of stalling on a diet and training program. 

The solution? Add some personality to mix things up!

For the past 5 years, I’ve been stressing the importance of building a core, essential wardrobe. But my goal was never to create a “one style fits all”. It was to give you the foundation to make it your own.

One of the advantages of working with me as a private styling client is a customized style and wardrobe. I’ve built wardrobes that could fit in a single backpack for my digital nomad clients. Leather jacket and black heavy closets for my clients who love rock and motorcycles.

It’s always been crucial for the wardrobes and styles I create for my clients to still feel like them, just a slightly cooler, more stylish upgraded version of themselves.

This year, I’m going to show you how to take it to the next level and develop your personal style. 

In the meantime, a great place to start is my annual “gifts you should get yourself” guides, which have a ton of my favorite pieces and accessories you can add to your essential wardrobe to give it more personality.

Get a head start on your 2020 style with my free Style Starter Pack Guide

I’m excited for what’s coming this year on The Essential Man and I don’t want you to miss any of it!

This year I’m adding exclusive style tip emails that I’m only sharing to my newsletter subscribers.

If you haven’t signed up yet, you can join the 12,000 daily readers of my newsletter below. As a bonus, I’ll send you 3 of my most popular guides to help you look better in 2020.

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