Men! Know Your Clothing Style (or Choose One of These Now)

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Gregory's been living the digital nomad life in Asia for as long as anyone can remember, helping clients smash their goals. He writes on topics like software, personal knowledge management (PKM), and personal development. When he's not writing, you'll catch him at the local MMA gym, nose buried in a book, or just chilling with the family.

A man’s style is the first thing you see when you think of any successful guy. You instantly picture them wearing some style of clothing. When I think of my BJJ instructor, he’s wearing a gi or other training gear. When I think of a millionaire friend of mine, he’s wearing a tailored suit with a tie. Which men’s style do people imagine when they see you?

If you’re unsure (or ashamed of the answer), it’s time to pick a new style. And there are plenty of men’s clothing styles to choose from. But it’s not only to change how people perceive you.

Why You Need to Choose a Style (Benefits)

There are five fundamental reasons you need to pick – and stick to – a single aesthetic.

1. Choosing a Style Will Save You Money

We all have those items in our wardrobes that have been there for years despite us having no intention of wearing them. It just looked so unique and cool in the store. Perhaps it represented who you wished you were. But it’s not you, and you don’t wear it, so let’s face it, it was a waste of money.

Then there is a much bigger category of clothes that you wear, but maybe you shouldn’t. The jeans with the intentional stains, those awful green corduroys, and that suit you still love but we all know hasn’t fit you for years.

After choosing a style and becoming comfortable with it, it will restrict what you can wear and what you can buy. That may sound like a bad thing (but let’s face it, you don’t really want the freedom to wear anything, do you?). It’s going to be great for your wallet, though.

You’ll buy fewer clothes, look better, and have more money to invest in something else.

2. It Makes Shopping Easier

Most men I know dread clothes shopping; they don’t know what they want, they don’t know what suits them, and they don’t know where to look. Most of them default to buying the clothes they’ve always worn. They’re easy to spot; they’re the 40-year-olds who still dress like teenagers – jeans and T-shirts with a big logo on the front and back.

I’m not saying that you can’t dress like that if you want, and if you are still a teenager or in your early 20s, have at it; you’re only young once. But if you are in your 30s or even older, it might be time to leave the kid’s clothes behind and

When you know your style, shopping for clothes becomes easier and more enjoyable. Instead of looking at rack after rack of things thinking, “Should I get this?” You can now ignore everything that doesn’t fit within your style.

3. Less Decision Fatigue Each Day

By now, everyone knows that Steve Jobs wore the same thing every day and that Zuckerberg and even President Obama followed suit. It was one less thing he had to think about – one less decision he needed to make. For someone as creative as Steve Jobs, it made sense.

But you’re not Steve Jobs, and you probably wouldn’t want to wear the same thing every day anyway. But by limiting your wardrobe to a specific style, you get the same effect. If you’re a shirt and jeans guy, just put on a shirt and jeans. If you’re a classic guy with a wardrobe full of classicly styled clothes, just pull something out and put it on.

The trouble comes when you have a mix of different styles and always have to decide who you’re going to be that day: ripped jeans and a tank top guy? a T-shirt under a suit guy? Or the preppy guy with a beige pair of chinos and patches on your elbows?

Staying consistent will make it easier for you and everyone else around you.

4. Your Style Shows People Who You Are & What to Expect

If everyone always sees you wearing threadbare T-shirts and sweatpants, that’s how they will think of you. It’s not that only the clothes maketh the man, but they certainly do maketh a big part.

If you wear a preppy style – like a model in a Ralph Lauren commercial – people will associate Ivy League Schooling and Money with you. And as I’ve said already, if you stubbornly keep wearing a hoodie and dirty jeans despite being fully grown, people will assume you are an old teenager who still hasn’t cleaned his room (or his clothes).

5. You’ll Look Better

If you have a wedding to go to and decide you’re going to “dress up nice,” it will be difficult if you’ve only got one suit. When you have a wardrobe that is a mix n’ match of different styles, you don’t have many options that go with many others.

On the other hand, when you only buy clothes within your style, you’ll have many more options for matching and creating a great-looking outfit. Then, when you find the style that suits you and acquire some decent clothes, you can look that great every day, not just when you have a function.

5 Styles You Can Adopt to Make Your Life Easier


Here I’m wearing a white shirt and a navy suit – super simple, super classic.

A classic wardrobe will never go out of style. That’s the point. If you want to look more masculine, a well-fitting suit with a white shirt will always look good, but you don’t need to look like you’re going to a black-tie event to reap the benefits of a classic wardrobe.

And, surveys have found that 80% of women find men wearing suits more attractive than when wearing casual clothing.

A classic approach to style isn’t an exact science; however, understanding the basics is all it takes to achieve a timeless silhouette. A capsule wardrobe is a great way to start.

  • Navy suit
  • Odd jackets
  • Beige Chinos
  • Shirts of simple colors and patterns
  • Pullover jumpers
  • Oxford or Darby shoes (formal and informal)


A simple preppy or new money look – I’m wearing a polo shirt with a cable knit jumper around my neck and a pair of beige chinos.

The preppy look starts with a classic wardrobe but throws out all the formal pieces and digs into the casual side. If you want to look put together without looking stiff or like you’re wearing your Dad’s clothes, a preppy wardrobe may be for you.

If you can’t picture this vibe, look at any Ralph Lauren model, and you’ll quickly understand.

  • Button-down shirts
  • Polo shirts
  • Quarter-zip Pullovers
  • Cable knit jumpers
  • Chino trousers
  • Textured or patterned suits

Monochrome or One Outfit

This is an easy monochrome look that you can change just by swapping out the raincoat for something shorter, less formal, etc. I’m wearing a pair of dark blue jeans, a dark blue hoodie, and a navy raincoat.

If you look good in one color (or one outfit), why not go all out and stick to it? When you know you’re only looking for clothes in a shade of grey (or whatever color you choose), shopping is much more straightforward.

Similarly, if you only want to wear one outfit every day, buy a bunch of them, and you’ll never need to worry about your image again.

Smart Casual

I have a beige T-shirt under a suit jacket and a pair of jeans for an everyday smart casual look here.

Although you can consider the preppy look smart casual, this is different. You’ve seen the alpha males who can rock a white t-shirt under a black suit or mix jeans with a sports jacket and pocket square.

It might seem like anything goes with a smart casual approach. However, there are some rules you shouldn’t break:

  • Don’t wear formal pants with sneakers
  • Avoid ripped or distressed jeans
  • Choose brogues, loafers, or boots over a formal shoe
  • Wear well-fitting (or tailored) clothes, and forget the baggy hip-hop style


I kept the T-shirt and jeans and ditched the suit jacket for a denim shirt to turn smart casual into just casual.

Here is where you get to wear those sneakers you love so much!

There are so many variations on casual clothing, but that doesn’t mean you shouldn’t still think about what you wear.

  • Colors and shades
  • Tight vs. loose
  • Solid vs. patterns
  • Sportswear, loungewear, beachwear, denimwear etc.