How to Dress Well: 9 Rules for Men

As men we often put less effort into our appearance in our adolescent years than our female counterparts, leaving us without the knowledge that we need to know how to dress well as we age. Despite this, knowing what to wear and when is incredibly important.

While it’s true that individuals have a unique taste and different subcultures have their style of dress, the vast majority of men have a similar idea of what constitutes a “well-dressed” man. Typically, it involves clothes that fit him well, smart pieces and a strict grooming and exercise routine that allows him to emphasize his natural features.

Men like David Beckham and Ryan Gosling are universally praised for their appearance across the globe, which is sufficient proof that it’s possible to give a rough set of rules which you can utilize when dressing. Through these rules, you’ll be able to take the stress out of looking great, turning it into a process which ensures that you can look fantastic wherever you are.

Why It’s Important to Know How to Dress Well

Appearances matter and to ignore this fact is foolish. It’s been proven in studies that attractive people get hired quicker, earn promotions faster and make more money on average. Part of this is because it’s challenging to respect and trust a person who can’t even take care of their appearance.

The external version of yourself that others see is a visual representation of your mind in the same way that you can learn something about a person if you see that they have an untidy desk. By taking care of your appearance, you can put forward your best self, and this can help you in personal, romantic and business relationships.

A key part of dressing well is fitting in with the crowd but sticking out with excellence. It would be odd to wear a suit to work in a factory, but it would be expected in a business meeting with a lawyer in the financial district of London. By dressing the part, you become part of the group; allowing you to assimilate and therefore form closer relationships more easily.

This is the reason why it’s rare for you to see a man in a smart suit with a woman in sweatpants and vice versa. You attract what you put out into the world, which means that you need to be incredibly careful with what you choose to wear. If you want to attract other athletes, wear athletic clothes. If you want to attract successful people, dress the part.

1. You Can Learn to Dress Better

The first rule is less of a guideline and more of an affirmation. You can learn to dress better, especially with the use of the internet. Growing up we often see men that stick out because they always seem to look stylish, almost like it comes natural to them. But that doesn’t mean that you can’t learn it.

Knowing how to look good is simply skill, and any skill can be learned and mastered given enough time. Fortunately for you, there are thousands of incredibly useful resources on the internet and plenty of style icons that you can use for inspiration.

As you begin to make more of an effort to dress better, you’ll typically start with a prescription approach. Which is that you’ll often read articles like this or copy and paste outfits from your favorite celebrities, which is completely natural and a great way to get started. As you become more knowledgeable, you’ll develop your taste and can adapt it for your unique purpose.

This is the point where you begin to standout and look truly stylish. Every stylish man has their unique twist. Otherwise, they wouldn’t look stylish, would they? They would look like everybody else, and therefore they would be mediocre. Over time you’ll be able to acquire more knowledge and improve your appearance and therefore yourself.

Resources we read and recommend

2. Prioritize Fit over Form

Although the clothes that you pick are important, the most important thing is the fit. The difference between a cheap white shirt and an expensive one, besides superior materials, is often in the cut of the fabric. By choosing well-fitting clothes, you can make them look far more expensive than they truly are.

Ideally, you should shop for items that look great off-the-rack, but if you can’t do this, mainly if you have an uncommon body shape, you must get a tailor. You don’t need to tailor everything that you own, but customizing your favorite shirts, pants, and jeans can make a significant difference in the way that you look.

A good tailor is a difference between stylish men that you see in magazines and the poor efforts of cloning it that you might see in a bar. By cutting the fabric of your clothes, you can prevent yourself from looking boxy, drawing the clothes in to make yourself look slimmer and taller. Plus, tailoring doesn’t have to be as expensive as you might imagine.

If you look for a local tailor in your area and are willing to take multiple pieces in at once you’ll often be able to get a huge discount and save yourself some money. However, if you’re currently trying to lose or gain a significant amount of weight you might decide that it’s worth waiting until you are closer to your goal weight before investing in tailoring.

3. Avoid Trends and Choose Classic Pieces

Perhaps the biggest mistake that young men often make when they are dressing is to follow trends. While you don’t want to be stuck in the past, there are clothes which look just as good today as they did thirty years prior. These classic pieces will always look good, they can help you to appear more stylish and will cause people to treat you more seriously.

An example of a trend might be ripped light denim jeans, which while cool for a short period will almost certainly be “out” within a couple of years. Unless you are obsessed with fashion and have a severe budget, you’re never going to be able to keep up with trends, and therefore it’s smarter never to try.

Instead, classic pieces like smart dark or indigo jeans, navy polo shirts and black leather shoes can be styled in a hundred different ways and will never go out of style. Plus, they don’t have to look “preppy” if that’s not your style. It could be quite the opposite, especially if you add some more interesting pieces like Chelsea boots and white t-shirts instead.

4. Use a Simple and Neutral Color Palette

When it comes to deciding on the color of your clothes, it’s easiest to stick to a neutral color palette. That doesn’t mean that you can choose some colorful pieces, it’s just that the bulk of your wardrobe should be filled with simple and neutral clothes. This allows you to match things far easier, it prevents you from looking ridiculous, and it makes your life easier.

In general, if you want to add a statement piece, it’s easiest to do it through a shirt whether it’s a polo, t-shirt or a dress shirt. The reason for this is that dark denim jeans will look great with nearly everything, but a statement pair of red khakis is almost impossible to match to anything. In contrast, a trendy red and blue striped t-shirt might go great with dark denim and Chelsea boots.

By sticking to a neutral and simple color palette, you’re staying safe, and that’s ideal for somebody that is still learning about style and fashion. It means that you don’t have to spend a considerable amount to look good and it gives you the classic clothes that you can later build upon.

Neutral colors

  • White, black, brown, navy
  • Olive, grey, khaki

5. Start from a Strong Foundation

When you’re first starting to dress better, you should make a conscious effort to form a strong foundation. To do this, you need to ensure that you have a selection of “base” clothes that you will wear very frequently, and which can go with a lot of other items. Examples of foundation pieces include dark denim, white t-shirts, tan khakis, navy polo shirts and a navy blazer.

The reason why these clothes are so important is that they can go with nearly everything and therefore you are likely to wear them more frequently. These are your training wheels, allowing you to learn to mix and match and create your style within a safe space where it’s hard for you to go wrong.

From there, you can pick up statement pieces and possibly even some trendy items that you can combine with your foundation. In this way, you can keep up with trends if you want but spend a tiny fraction of the cost because the majority of your outfit is formed of your foundation items.

6. Don’t be Afraid to Invest in Quality Pieces

With this in mind, when you’re buying foundational and multi-purpose clothes, you shouldn’t be afraid of investing. After all, you’re going to be wearing them a lot, and therefore you want to get the best pieces that you can afford. A dark pair of denim jeans, for example, can last you for up to a decade if you buy a great product and take care of them over time.

Although there is undoubtedly some “marketing cost” to buying name brand and luxury items, in general, the more, you spend the higher quality the clothes will be. Better quality items will not only last longer because they are built from stronger and more durable materials, but they will also look better during their lifetime.

Take the humble white t-shirt for example. Sure, you can pick a pack of ten up for chump change, but you could spend double that on a single t-shirt if you choose a luxury brand. This might seem crazy, but if you care for that piece, you can wear it over and over again each week. It’s going to look a million times better, it will fit you perfectly, and it will feel like a warm hug rather than a harsh itch.

By investing upfront in your foundational clothes, you can start from a strong base, all but ensuring that you look good at all times. The key pieces to invest in include jeans, suits, leather shoes and plain white shirts. Although there is more to choose from, these are your everyday picks that every man needs.

7. Care for Your Underwear

Just because your underwear isn’t visible at all times, that doesn’t mean that you should forget about it. Imagine you pick up somebody at a bar, and you head home, and as they are taking off your tailored white dress shirt and dark denim jeans, they start to see your SpongeBob SquarePants underwear. What does that say about you?

For the vast majority of men, the best underwear that you can buy will be a black trunk which has some elastic or latex in it. This helps them to be form-fitting, even after they are washed hundreds of times and the dark color prevents them from becoming discolored or stained.

The same is true for your socks, which should ideally be a dark black or navy unless you are wearing athletic clothing. Regardless of what you might think, luxury socks and underwear feel a thousand times better than value pairs, and if you care for them properly by washing them a low temperature and air dry them rather than using a tumble dryer, they can last for years.

8. Don’t Forget About Your Body and Grooming

With all of this focus on your clothing, it’s easy to forget about what’s underneath it. Your grooming and body have a massive impact on the way that you look, arguably even more so than the clothes that you pick out. For this reason, it’s worth your time to sharpen out your diet and workout whenever possible.

You’ll find that as you slim down and start to see your abdominal muscles, you’ll not only look better naked, you’ll fit your clothes amazingly, and your jawline will become more defined and masculine. Which brings us to our next topic, your grooming regime.

The bathroom isn’t only for the ladies, gentlemen. Every morning you should have a consistent grooming regime that includes shaving (or trimming your beard), washing and applying moisturizer to your face. At the very minimum, these three steps will allow your skin to shine.

Beyond this, you should consider getting a haircut at least once per month and perhaps more frequently, especially if you have short hair that can become disheveled more easily. Of course, you should also care for your dental hygiene to keep your teeth white and as straight as possible.

9. Look to Others for Guidance

You’re not on this journey alone, and there is plenty of guidance out there if you know where to look. Websites like this are incredibly helpful for teaching you what looks great and what doesn’t, but you should also search for your inspiration and guidance. Instagram is an excellent place for this, but often celebrities are an even better alternative.

Celebrities like movie stars and sports players have a nearly endless supply of money to spend on clothes, plus a team of talented stylists, which ensures that they always look incredible. While you might not have either of those, you can get a glimpse at what those with this luxury are buying and doing, and you can emulate it with your twist to look fantastic.


Knowing how to dress well isn’t difficult, but it’s not something that you’re going to be born with. It takes effort, research and inevitably a few fashion blunders before you can nail it down and look stylish day in and day out. By following these ten simple rules you’ll be on your way, but don’t forget to try new things and innovate with your style.

Fashion serves a purpose in orientating you in the world and helping you to reach your goals, but it’s also an expression of your personality. Learn to love it, embrace it and live the life that you’ve always dreamed of. Who knows, maybe you’ll be a style inspiration for others around you?

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