10 Timeless Men’s Fashion and Style Tips: Dress Timeless Without Stress (Updated)

I’ve found a strange pattern on my journey of personal development…

Style and fashion matter.

It’s important to many area of life: dating, sales, business, presentation, grooming, etiquette, and so on.

Yes, you have a few tech billionaires who wear what they want (Steve Jobs, Mark Zuckerberg) but most successful people understand the importance of looking presentable.

If you believe me, you’re way ahead of my young self. For decades, I disregarded fashion because I thought it was what was on the inside that counted and getting good grades was all that mattered. Obviously, that backfired for years in my dating and professional life.

 

The truth is that your outer world is a reflection of your inner world. If your room, hair and outfit is a mess, your mental health and effectiveness as a human being are likely a mess too. There are exceptions, but studies have proven that women are quite effective at judging us in this way.

Also, you just appreciate someone who dresses well and takes care of himself more. It looks cool. It shows they care about their image. So let’s not be hypocritical here; we are all superficial on some level for our own good.

Let’s crush these limiting beliefs together. One of the top Men’s fashion Youtubers Alpha M, otherwise known as Aaron Marino, was voted best dressed in high school even though he was dirt poor. He did it by buying intelligently at a thrift store.

It just goes to show you how you can still fail with money while others succeed without it. I have spent hundreds of dollars on clothing I would be embarrassed to wear now. Today, I’m going to share with you how to hack the process so that never happens again.

Why We Look Horrible Even When We Spend Lots of Money

Let’s start with why this happens. Most people have horrible fashion sense. Here’s an example to illustrate. I was listening to a podcast where they were giving an average guy named Joe a makeover. He wore awful clothing and it was revealing when he started reasoning out why he thought it looked cool.

He chose colors and t-shirts because they were his favorite color or design. But he ended up looking like a strange greenish banana. He didn’t see anything wrong with his fashion even though it was clear to others how horrible it was. This is the danger of bad fashion sense. 

Instead, get some help from people who know what they are doing.

The Philosophy of Timeless, Simple Fashion For Busy Men

That’s why this article is all about a few core philosophies:

  • Spending minimal time in your life buying clothes because you are busy and because you don’t have to if you understand some fashion principles.
  • Using timeless outfits that will always be in style to look sharp.
  • Having a couple core colors that always look good for each piece of clothing, which can lead to dozens of variations of outfits despite a minimum wardrobe.
  • Spending a little more time to learn more about fashion so that you appear to know more than 99% of people out there (trust me, it’s startling how easy this is).

Why Fashion Helps You Earn More

I don’t want to go too deep into the reasons why fashion is important because some of it should be obvious. It’s like explaining why exercise is important.

But I must talk a bit about why style can make you earn more because it is overlooked yet so important.

I have read countless wealth creation and sales books like Think and Grow Rich or How To Win Friends and Influence People that mention how fashion is important. In some of the books, they have stories to prove this.

One of them was a man who bought a great suit that he couldn’t afford on credit. It made him look and feel so good. Plus, it made him look the part of a successful businessman. He assumed the image of a successful man and eventually scored a business deal from someone who kept passing him on the street and admiring his fashion.

I don’t recommend buying clothes on debt. But what I do agree with is that looking good makes you feel good. And if you feel good, you will be more confident and perform better. Plus, you look the part and people assume you are someone worth working with.

Now, let’s look at a real story that you can relate to. An article by Neil Patel explains how he tested out wearing a suit versus regular clothing during his sales meetings. Neil does a lot of these and usually closes 1 out of 4 people. But with his suit, he went from 25% to a 40% closing rate. This brought in an extra $692,500 that year. He also said his clothes and accessories helped him form a lot of valuable business relationships.

Neil’s story is a great case study because he mentions in the article that he’s someone who does not care about clothing or superficiality. He wears suits now because the numbers do not lie.

Note: looks aren’t everything and you can still be a horrible person on the inside even if you dress well.

I have been watching a decent amount of men’s fashion advice videos and videos where women give fashion advice.

Like these:

I have also been asking women my age for advice. I have asked maybe 20+ that have given decent responses. It’s surprisingly one of the best ways of starting a conversation. Women love fashion. They are much more open to talking versus using a pickup line.

What I have found from these videos is exciting:

Men are encouraged to keep it minimalistic and simple!

They are told to leave the intricate, complicated, fancy stuff to the females.

I’m so glad about this because it means less work and less accessories or extra clothing to buy for us!

It also goes back to Steve Jobs and Bill Gates:

CEOs and founders have a lot of responsibilities and therefore they have to deal with limited cognition, willpower, and decision making.

To avoid decision fatigue, they have to limit all the small choices they have in a day: like choosing outfits.

It’s a real thing.

That’s why I was SUPER excited about this.

I don’t like spending a needlessly large amount of time buying clothes or picking outfits everyday. I’m all about productivity so it’s great that I don’t have to and still fall into what women love the most.

Without further ado, here are ten fashion tips you can live by that will make you in style and keep you in style for years to come with minimal effort:

1. Spend Somewhat More For Quality (But Not Too Much)

For many consumer goods you buy, you get rapidly diminishing increases of quality as the price goes up. The reason is simple. There’s a limit to how “high quality” it can get. Here are some examples:

Photo and video cameras. The picture quality between a $100 one and a $1000 one is huge. Beyond that, you’re spending massive amounts of money for small increases in quality.

Jeans, socks, and underwear. Can you tell the difference between a $2,000 pair of jeans and a $200 pair? Probably not, right?

This is great news. It means you don’t have to spend tens of thousands of dollars to be the most fashionable. Most people can’t tell the difference either, so that’s a great area to cut costs and avoid getting scammed by luxury brands.

My philosophy is to spend a moderate amount for quality, but not too much. If you spend too little, you get horrible quality clothing that rips or shrinks quickly. Others can also easily tell it’s not the best quality. However, if you spend a moderate amount more, you hit the point of indistinguishable high quality.

A moderate quality lasts longer, and looks just as good as something that costs a hundred times more.

The greatest difference in quality comes from that initial few jumps in quality. For the minor articles of clothing mentioned (like socks), one or two jumps in price tier from the cheapest option is enough. For more important clothing, like suits, chinos, and collared shirts, three or four jumps in price are more suitable.

For a suit, that might mean a $1,000 to $2,000 suit rather than a $100 suit. For a t-shirt, that might mean a $30 to $60 one from Banana Republic versus a $5 one from Target.

For shoes, there is a big jump in quality between $100 and $200, and another big jump at $400. Stick around the $200 to $400 range for the best bang for your buck.

Beyond those price jumps, the extra features aren’t worth the price. I’d avoid the $10,000 to $50,000 suit and $100 to $500 T shirt at all costs.

2. Minimalism and Simplicity Are Key

When you ask beginners about fashion, they assume you need six or seven articles of clothing draped around you to look cool. But when you actually look at the men who were something that’s still fashionable 40 years later, it’s simple. Just a well-fitted collared shirt and jacket can do the trick and last the test of time.

David Beckham Fashion Advice Example
David Beckham, a star soccer athlete and fashion icon, rocking a simple collared suit and jacket beautifully on Instagram.

This is great news because it means less clothes you have to manage, less time you have to spend choosing outfits, and less money you have to spend. 

Our wardrobe and closet does not have to be the nightmare we envision of thousands of clothes in a pile that would take hours a week to organize and maintain.

We can do fairly well by being fairly minimalistic and simple, which is what girls want.

Obviously, don’t overdo it as it would be foolish to believe that some variety is always a bad thing.

1-3 versions of v-necks, boots, jeans, collared shirts, plaid, and suits could just about do it.

I didn’t really like the v-neck because I thought it was for only muscular men.

Having asked enough girls though, it seems that it still works well for non-muscular men, though of course they would prefer a muscular male.

Why A Minimal Wardrobe is Great For Busy, Ambitious People

Second, let’s talk about willpower. There is a reason Barack Obama, Steve Jobs, and Mark Zuckerberg wore the same outfit everyday.

To conserve their limited willpower. Studies show that if let it, your willpower drain in a day, leading to worse decisions and a weak mind vulnerable to temptations. They need that willpower to make critical decisions rather than waste it on unimportant choices, like which outfit to pick. Obama explained it like this:

“You’ll see I wear only gray or blue suits. I’m trying to pare down decisions. I don’t want to make decisions about what I’m eating or wearing. Because I have too many other decisions to make.”

3. Keep It Timeless: Timeless Colors, V-Neck’s, and Suits

This is the key.

Don’t try and choose crazy colors because you think they “look cool.” Don’t try and buy some wacky designs because you think you’re going to look unique. Don’t try and be the “trendsetter” when you suck at fashion.

It just backfires and makes you awful. And even if it’s in fashion right now, it will go out of fashion in ten years. And you will be embarrassed. Like The Rock:

On the Internet, I’ve watched a lot of makeovers where experts come in to help an average man with his fashion. One of the most common problems is a severe lack of understanding of colors. They choose off-the-wall, crazy colors because it “looks cool” or it’s their favorite color, not realizing the colors clash or are just weird.

Here are the colors you should stick to:

  • Black
  • White
  • Gray or Charcoal Gray
  • Navy Blue

These colors look well for suits, polo’s, t-shirts, v-neck’s, and dress-shirts.

Once you’re fully settled in these and know a bit more about fashion, you can venture into:

  • Light Blue
  • Medium Blue
  • Silver
  • Brown

It may seem boring but these basic colors are timeless. In fact, some of the most fashionable men out there probably wear only or mostly these colors. I bet you. Check out the suits David Beckham wears. You do not need flashy colors to look good. It’s less stress juggling more colors anyways.

Here are some of the top colors and designs you should avoid:

  • bright orange
  • purple
  • yellow
  • lime-green
  • stripes
  • polka dots
  • crazy patterns

Don’t try and do something crazy. Leave that to professionals in fashion who do this full time.

For you, stick to simple, solid colors, with no (or very few) stripes.

I suggest you only stick to black, gray, and white. Common timeless outfits include v-necks and suits.

Think timeless. These colors will be in trend 30 years from now just like they were 30 years ago. You don’t want to have an outfit or trend that goes out of date in a few months. The same concept applies to not just colors, but outfits.

If you do venture into other colors, remember this…

If you cannot resist buying other bolder colors, keep these colors to 5% of your wardrobe. These should be a tiny “spice” to the rest of your outfit. Adding too many colors makes you look like a rainbow clown.

I suggest the color red because studies show women find this more attractive and people find it more persuasive. This could be linked to the history of the color red, which  only the wealthy and high status could afford it. Humans may still be genetically wired to unconsciously assume you are high-status when they see red.

Wear Timeless Suits. Ladies Love Them.

Suits are one of the big ones. Most women who are asked say that they love a man wearing a suit.

A classic suit is always in style.

There are men who wore suits in the 1940’s who would still look completely in place now. As I explained with Neil Patel, a good suit can help you outside of just dating. It can help you in business.

Your first foundational suit should be versatile, timeless, and smart. Therefore, it should be a solid navy (preferred) or a solid charcoal gray. It shouldn’t have stripes because it’s not as versatile. It should have 3 buttons, no more and no less. Source: Real Men Real Style

Keep it with these safe colors. If you want to add some spice, you can do it with a colorful tie or dress shirt.

Suit Supply has great $400 suits that fit well and are great quality. Some of them have free shipping, returns, and tailoring. Absolutely make sure it’s fitted. See the next heading to see why it matters so much (especially for suits).

4. Get It Fitted

The right fit makes all the difference. Many people have incredibly muscular bodies but fail to show it off because of excessively baggy clothing. Having the right fit can really complement your height and physique if you do things right.

Having the right fit can really complement your height and physique if you do things right. The wrong fit can fail to market you as the incredible person you truly are.

Most people don’t know what the right fit is. They think it’s good, but it’s usually too loose.

If you have money, consider spending around $30 to $40 for a tailor to come in to tailor your dress shirts and suits. It is usually worth it.

If you want to save some money and try to buy a fitted shirt off the rack:

Here’s a general rule of thumb: 

Measure your neck circumference and arm length. Those measurements are on dress shirts when you buy them and it’s easy to compare. What people miss are the chest and waist lengths. You don’t have to measure these since shirts don’t even list these measurements.

What people miss are the chest and waist lengths. You don’t have to measure these since shirts don’t even list these measurements. This is what you can do: try on the shirt and look at yourself in a mirror. Put your arms out to either side. There should be an inch or less of room on either side of your chest and waist if you pull out the shirt.

There it cuts off on the shoulder part of your suit, jacket, or dress shirt should be at the end of your shoulders.

There’s plenty of videos on Youtube about how dress shirts, jeans, t-shirts, dress pants, and everything else should fit.

If you have the money, you can spend around $40 bucks to get it custom tailored and it will be worth it. You want to only do this for the things that matter, like a suit or dress shirt.

For something like t-shirts, learn a bit about proper fit to buy it right off the rack.

5. Wear What’s Comfortable For You And Fits With Your Lifestyle

The function of your clothes is one of the most important factors of your purchase decision. Buy clothes you are going to wear often. If you’re wearing something that doesn’t fit with the context of the event you’re attending, you’re screwed no matter how expensive or high quality it was.

For example, don’t wear a suit to the gym and don’t wear a t-shirt and jeans to a formal event. In cases like these, choosing an appropriate outfit for the event (the function) matters more than fit or fabric.

Also, push your comfort zone with your choices, but not too much. You still want something that comes natural to your personality. Even if you look attractive, if you don’t feel like it really represents you, that will seep through on a subconscious level and make you look less attractive.

I think the difference between a good and great fashion expert is that they understand this. Don’t force a nerdy outfit if you’re more of a jock.

6. Don’t Try Too Hard

If you try overly hard to showboat something, people can sniff that out as compensating or faking it.

This happens all the time when people rent expensive cars or buy fake watches and pretend it’s real and they own it.

Women and men sniff it out because it’s over the top.. and it’s a turn-off.

The lesson is simple: don’t be super flashy with your fashion and try-hard – it’s off-putting.

An example would be an overly playboy or bad boy outfit.

A quick reference back to the Neil Patel article: he also experimented with buying a number of different watch brands. He found that an overly flashy and clearly flamboyant $28,000 watch was looked down upon while a simple, non-fancy $100,000 watch got noticed and got him more business contracts.

The point is: don’t be overly try hard in trying to look successful

7. Make Sure It Fits Your Body Type

Make sure the clothing fits you well.

The difference between a crappy outfit and a good one could simply be the size that you choose to wear it.

Based on me studying fashion advice, I have found that I have usually been choosing a size that’s usually overly baggy: I used to choose a large t-shirt even though I have a smaller body.

If you don’t know, choose the smaller size so it wraps around your body better. (may be different if you have a bigger or overweight frame)

channel art

8. Realize That The Most Expensive Choice Isn’t Always The Best Value

Some stores, like Hugo Boss, rip you off. They charge two to five times more for the same quality and design of clothing.

OK, if you’re rich and don’t care, you can skip this section. You can even hire a tailor to come to your house if the time cost of going to the mall isn’t worth the money you could be making.

However, you can definitely save a ton of money by spending a bit more time choosing.

Only buy clothes you set out to buy. You can often find great deals at the discount section and I encourage you to take a look. However, beware of buying clothes you never should have because it’s on sale.

Everyone has a piece of clothing that is too big or small or just a weird color that they bought because it was on sale, even though they’ve never worn it. Even if it’s cheap, you’re still wasting money on something you will never use! Don’t fall for sales gimmicks.

Here are some of the best clothing stores to go to that have great quality clothing but are still affordable. This is ranked from worst quality and cheapest to best quality and most expensive:

  • H&M (decent quality but wears quickly)
  • JC Penney
  • Macy’s (The American Rag section and the J. Ferrar line are great)
  • The Gap (great quality and price but more for casual clothing. It’s a versatile brand that fits almost everyone.)
  • Banana Republic

This video also has some great options:

The Tie Bar is a great place for affordable ties. See Point #10 on this article to understand why you shouldn’t waste time spending too much extra on a tie.

For shoes, here are you best options (starting at affordable and going to higher quality and more expensive):

  • Macy’s
  • Zappos.com (affordable and has almost anything. Flexible)
  • DSW (slightly more expensive, good quality)
  • Nordstrom (great but for more formal and business-type shoes)
  • Cole Haan
  • Johnson Murphy

If you are really on a budget, here are some tips to really the most affordable clothing:

  • Sign up for email newsletters on Brand websites for coupons.
  • Go straight to the discount section (often, the size won’t fit you, but sometimes you’ll be surprised).
  • Go to outlet counterparts of stores.
  • Go to Target, Marshall’s, or TJ Max.
  • Go to Thrift Stores.

9. Never Buy Clothing You’re Iffy About. Don’t Have Bad Clothes In Your Closet.

Have you ever spent money on clothing you’ve barely worn or never wore? I have. And I’m a very frugal guy. But over my lifetime, there’s probably a good 300 to 400 dollars worth of wacky clothing I never wore.

Because of my naivete, I bought things like a bright blue, plaid hoodie from Hollister and a deep Ed Hardey v-neck that I’ve never worn even though they cost me an arm and a leg.

Lack of fashion knowledge can cost you when you are most vulnerable. I was frugal for many months but ended up splurging on random clothing like this that I’ve never worn.

I watched a video on Youtube about a homeless man who sleeps with women everyday despite being homeless. The most striking thing about him was that he was well-dressed and well-groomed despite being homeless. How?When they asked him how many bad outfits he had, he said he had none.

How? When they asked him how many bad outfits he had, he said he had none. All he was were 3 awesome outfits that he kept clean. He would steal cologne and grooming supplies from the mall.

What’s my point? This man was better dressed than most men because he adopted a minimalist wardrobe with no bad options. 

If your wardrobe has bad clothing in it you’ll never or will rarely wear, remove it. 

You want clothing that you can wear confidently because it fits your personality. If you are iffy about it, pass on it. Trying to wear something that’s not you is like trying to fake a personality. It doesn’t work! I’ve tried.

10. Spend Less On The Items Most People Will Never Notice

Ties are one of those things where 99% of people can’t tell the difference between a $10,000 tie and a $200 tie. The same goes for underwear and socks, something that you’ll barely even show to others — if at all. This is an easy place to save money or waste money with close to no extra impact for the money you spend. Save your cash.

The Tie Bar is a great affordable yet quality website to buy ties.

Many big companies cheat customers by selling the same piece of clothing for multiple times the price by pumping up the brand name. It’s often the same thing in every way as a competitor product that doesn’t have the logo. But the often successfully trick you into thinking there’s something more there.

Sometimes, the quality is even worse but people will pay through the nose for the logo. I’m sure you’ve experienced this yourself. Despite my frugal Asian upbringing, I’ve fallen for this too. Here are some big examples: Beats by Dre Headphones versus any other brand headphone or The North Face jackets versus any similar jacket with a different logo. Air Jordans and Yeezy shoes are a similar thing. A pair of Yeezy’s can go for $2,000+.

Here are the biggest brands to avoid according to my trusted source, Alpha M:

  • Polo’s or other clothing by Ralph Lauren or Lacoste
  • Jos. A Bank
  • Men’s Warehouse
  • Armani
  • Diesel
  • Abercrombie

Note: the exception to this rule is that occasionally the logo is worth it. For example, I have asked many girls in the area and they love and look for the Ralph Lauren logo. However, this is different for each location you live in so figure out what works for you.

Most of the time I overemphasize on this, I pay too much and get underwhelming results. Don’t do this often. For example, I paid for quite a few Ralph Lauren polo’s. It did make me look more presentable, but there was a very negligible, noticeable change in results in any part of my life. Girls definitely didn’t flock to me just because I was wearing the shirts. Also, each shirt cost $50 to $80. It cost an arm and a limb for me. It was too expensive given my limited budget and I won’t do it again anytime soon.

Also, each shirt cost $50 to $80. It cost an arm and a limb for me. It was too expensive given my limited budget and I won’t do it again anytime soon. Maybe when I’m super rich.

Don’t Focus On The Minor Low-Impact Items

A common mistake for beginners is that they will focus on small minutiae while overlooking high impact points of fashion. Let me explain:

Have you ever heard of Pareto’s Principle? Essentially, it says that 80% of the results come from 20% of the effort, and 20% of the remaining results come from 80% of the effort. Therefore, focusing on the 20% matters more.

In the case of men’s fashion, the 20% is mastering your fit, fabric, and function.

If you don’t have that down, it doesn’t matter what else you do, you’ll look bad. Don’t make the mistake of focusing on pointless minutiae, like having a fancy tie knot or a bizarre pocket square, when your suit doesn’t fit, is low quality, or doesn’t work with the event you’re attending.

Conclusion

In summary, master your fit, fabric, and function — and the rest will follow. Also, keep these timeless secrets in mind:

  • Use simple solid colors, especially black, white, and gray, and clothing that is interchangeable.
  • Collared Button-Up’s are timeless when it’s cold outside.
  • Simple, Minimalistic outfits, like jeans, boots, a shirt, are fine. You don’t have to over do it as a man.
  • Avoid the “child’s look” (t-shirt, hoodie, and tennis shoes) if you’re no longer a teen.
  • A classic suit works wonders.

Looking back through my life, there were plenty of moments where I walked through numerous clothing stores wondering what to buy.

I would come out of the store bewildered, not knowing what to buy because I had no knowledge of the science of men’s fashion. If I did buy something, it would be something crazy-looking and expensive that I would end up never wearing, like a Ed Hardy deep v-neck.

I’m so glad that I took some time to invest and learn about men’s fashion. I realize now that the materials and ingredients were always there around me. The stores I wanted to go to were always where, but I just didn’t know what to buy or look for.

Rather than looking for a dress-shirt or a proper fitting pair of pants, I might come out with some crazy-colored t-shirt I thought looked cool. This is a great example of learning from people who know what they’re doing.

Fashion is one of those areas where someone who is below-average in skill can be lead to believe that he is great at it. Learning about the standards of fashion and what other girls like really helped eliminate my bias. I see this in others to an extreme extent and so you have to be careful.

If I were to summarize this whole thing in as few words as possible, it’d be:

Keep it smart but simple, wear what’s timeless, wear what’s comfortable to you, wear v-necks, black and white simple colors, suits, boots, jeans, be willing to spend a little more for quality.

Don’t spend too much on a specific article of clothing.

Certain things 99% of people can’t tell costs 100x more so save yourself the cash.

Examples include jeans and ties. Spend a reasonable amount (don’t be super cheap) but don’t spend thousands or even hundreds.

Fashion differs slightly depending on your culture and geographic location. People in a certain area might like more preppy-clothing.

According to Realmenrealstyle.com, remember the 3 pillars of Fashion success: fit, fabric, and function.

  • Fit – Does it properly fit your body frame well?
  • Fabric – Is it good quality? Will it last?
  • Function – Are you wearing it for the right occasion?

What you choose to wear can have a deep effect. You could be the most successful, wealthiest, most intelligent businessman on earth but if you dress like you’re a 17 year old teenager with a messy t-shirt, men and women sometimes won’t even give you a chance to open your mouth.

They often have nothing to go on but your looks.

I’m starting to see the importance of looks now. There are adults who have done fairly well and somehow managed to get through life without having to care at all about their fashion or grooming. Because of that, they have disheveled hair and crumbled jackets that they wear. Even I can’t deny it’s not a good look.

You’re definitely selling yourself short if you’re an amazing guy and you choose to dress very poorly. Most people don’t realize that your fashion is a choice. Many people have sort of just got used to it being a routine. It is definitely something that is a choice and that can be changed for the better.

And make sure you have confidence. Wearing clothes that make you look good will help with your confidence. I’ve done articles about improving confidence if you want more info. 

What have you learned about timeless clothing advice that can almost be applied anywhere in the world that you can back up with data? I’d love to know.

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