20 Rules for Dressing Well for Men

No amount of charisma, skill, and intellect can overcome the wrong impression a man makes when he dresses poorly. So it won’t matter if a person looks like Brad Pitt, people will see them in a bad light if they are wearing their dad’s oversized suit to a party.

Although this fact may seem unfair, it’s just how the world works. Unfortunately, great style is challenging to develop

Thankfully, learning how to dress well is not rocket science. To help make things easier for men, here’s a compilation of the top rules that men should follow to look sharper and more stylish. 

How to Dress Well: 20 Rules

Ready to be the next style icon? Keep these rules in mind when dressing to impress.

Rule 1: Shop for Basics

For men of all ages, shopping for go-to pieces is crucial. These items will serve as their wardrobe’s foundation for the coming years. Because of trends, it may be hard to find essential pieces in department stores. But don’t let the rows of daring and crazy polos and pants be a distraction.

Men’s closets should be filled with items they can easily mix and match. Some of the fundamental pieces men should shop for are plain t-shirts, neutral-colored polos, a good jacket, and a pair of jeans that fit them well

Shopping will be more comfortable and more time-efficient once guys find a label that understands what they want. For example, when looking for button-downs, men can head straight to J. Crew. For jeans, they can try Levi’s. 

Rule 2: Think About Footwear

Some men don’t think about their footwear much- they just slip on the first pair of shoes they find in the morning. However, people, especially women, pay close attention to what shoes a man is wearing.

A guy’s favorite pair of dirty and beat up converse may not look good with their work outfit. So think about replacing these relics with something that looks better. Once men vamp up their shoe game, they’ll immediately notice that compliments will start flowing.

But don’t worry. Men don’t have to shell out thousands of dollars for good shoes. Invest in a good pair of sneakers, gym shoes, leather shoes, sandals, and boots that will last for years. These essential pieces are all men need.

Rule 3: Dress According to Your Body Type

Not all men look the same, and so they can’t expect all style rules to work for everyone equally. Aside from dressing in style, men should also prioritize dressing in pieces that suit their bodies.

Men must pick clothes that flatter their specific body shape, hairstyle, and personality. For guys who have a broad chest with a narrow waist like Gerard Butler, they should draw attention to their hips by wearing v-neck shirts, and foregoing skinny cuts. 

For those who have more of an athlete’s body, with broad chest and shoulders like Michael B. Jordan, they can be daring with anything they choose to wear. For skinny men like Jared Leto, their goal should be to add shape by layering clothes and wearing items with structure. On the other hand, happy eaters like Seth Rogen should master how to emphasize their shoulders. 

Rule 4: Sometimes You Need to Layer Clothes

Men can feel intimidated to wear layered clothing because they are afraid of making mistakes. But wearing clothes in layers is not only fashionable but practical as well.

For beginners, starting with two or three layers to keep your look simple is a great idea. Also, try mixing and matching different fabrics and textures. While it is advisable to experiment with patterns, be careful not to repeat the same print since it will look redundant. 

Another key thing to remember is to keep bulky clothes on the outside, such as sweaters and coats. And always tuck in the thinner first layer of clothing.

Rule 5: Wear Clothes That Fit 

There’s a reason why Ryan Gosling and George Clooney look good in everything they wear. It’s because they understand the power of wearing clothes that fit them well. Wearing clothes that don’t fit will throw off a man’s body shape. 

Guys who don’t want to end up looking shorter or fatter than they already are should avoid excess fabric at all times. Just because looser clothes are more comfortable doesn’t mean they look good. Unless guys are going for a baggy shirt and tight jeans combination like Kanye West, forget oversized garments.

Rule 6: Research About Matching Colors

When dressing up or down, wearing the right color combinations can either make or break men’s outfits. By choosing the right shades, men can achieve a more balanced look. 

First, men should get acquainted with the color wheel. Examine it and identify similar and complementary colors. Of course, color combinations may be quite bold if men use this guide.

For men who love wearing navy, it’s better to forego black and choose beige or white for a classic look. For those who usually go for soft tones like beige, they can pair it with light hues such as blue or tan. On the other hand, black clothes look better when mixed with lighter tones such as white and baby blue. For a striking look, men may wear black with red and other bold colors. 

Rule 7: Select Belts Carefully

Belts are probably the most undervalued fashion item for men. This vital item will keep men’s pants from falling and needs to be thought about carefully. Before choosing a belt size, make sure it fits well. For example, men with a 32” waist should buy a belt that is 34” to 36”. 

Flat belt buckles should be paired with professional clothes, while larger buckles work well for casual outfits. 

Rule 8: Wear the Right Jeans

Choosing the right jeans used to be a walk in the park. Men either wore black or blue – that’s it. Now, there are countless choices for cuts, color, and finishes to make any man feel confused. 

When shopping for jeans, the fit should be considered a top priority because this will ensure comfort. Men who want looser jeans should never go for baggy pants, ala Eminem in the 90s. Simply pick a classic or relaxed fit since those are designed to be looser on the thighs.  

Rule 9: Don’t Go Overboard with Patterns 

When men comb through their closet, they shouldn’t find a myriad of bold patterns that serve as statement pieces. Men who are beginning to explore their style should stick with solid colors first. Only when they have developed more confidence should they try to pull off patterns like stripes or plaid. 

Rule 10: Look for External Inspiration

Prioritizing style for men is a challenging task, especially if they are around people who don’t pay attention to what they wear. When it comes to elevating looks, discovery is vital.

Seek inspiration and advice from others, but don’t let them dictate your style. Men may also search for celebrity looks online and in magazines. It also helps to find a style icon with the same body type and examine how they dress. Take note of similar items and try to use the similarities as inspiration for extra-challenging styling days. 

Rule 11: When in Doubt, Stick to Neutral Colors

When going for a job interview, a date, or another important event, it can be daunting to choose the right colors of clothes. Neutral colors such as navy, brown, olive, white, black, khaki, and gray are not overpowering and can match each other seamlessly. It also looks very masculine and well put together.

Rule 12: Invest in a Suit

Whether men like to dress to impress or not, they should have at least one suit in their wardrobe. This outfit is perfect for occasions men have to look dapper and more refined, such as weddings, important meetings, and funerals. 

Think about it. It’s impossible to impress your boss or your girlfriends’ parents when you don’t know how to sport a suit when the time calls for it. 

Rule 13: Master Casual Clothes

Some men are so used to wearing suits at work that they go to the office on casual Fridays overdressed with their suit and smart shoes, sans the tie. 

Dressing up is as important as dressing down, especially when men want to build a deeper connection with their peers. Get to know the key pieces in a man’s wardrobe that look casual, such as flat-front trousers, unbuttoned button-downs, colorful socks, and trainers. Dressing down does not have to equate to athleisure clothes. Men can still look put-together in many ways, even if they are not wearing a suit.

Rule 14: Don’t Be Afraid to Experiment

Men who are familiar with general styling rules can experiment with trends. While they might make mistakes in the process, at least they’ll learn a lesson or two on what looks good on them. 

Some many labels and shops cater to guys of all ages, especially those in their 20s. Integrate trendy items, such as bulky shoes and summer sandals, with essential elements, such as crisp white polos, if you want to make a statement at work or a night out.

Rule 15: Take Care of Clothes

Stylish guys know that it is crucial to take care of their wardrobe. Clothes should be considered a valuable investment, so it makes sense to learn necessary repairs such as replacing a missing button, getting rid of stains, polishing shoes or fixing a loose thread.

It is also vital to know how to fold your clothes properly. Or at the least, buy hangers. Also, take time to shop for fabric-safe detergent, a shoe cleaner spray, and an iron.

Rule 16: Get Rid of Unnecessary Wardrobe Items

Most men can’t find their great pieces in their wardrobe because they are covered by a bunch of clothes they never wear. Purging the closet is one of every guy’s first steps in improving their fashion. This way, they can get rid of items that are not age-appropriate. After all, tattered t-shirts serve a better purpose in the donation bin than at social functions. 

Rule 17: Accessorize Your Outfits

Many guys think they cannot wear accessories as women do. While their options may be more limited, it doesn’t mean men can’t show off their style with accessories. One of the essential accessories every man must have is a watch. When getting one, think about where it can be worn. Will it be for work? Or maybe casual dinners? Or formal events? 

A simple bracelet or a pocket square can also elevate an entire look. However, be careful not to go overboard with accessories.

Rule 18: Choose Sunglasses Carefully

Every man should have a pair of shades to protect their eyes from the sun, be the final touch for an outfit, and hide their raging hangover. When men choose sunglasses, they should pay attention to their face shape. Also, ensure that the glasses are not sliding down on the nose area because it looks and feels distracting.

Rule 19: Bond with Your Favorite Barbers and Tailors

As men age, they understand the power of well-fitted clothes and good haircuts. For guys who want to do well in these departments, befriending their tailor and barber is an excellent idea. This way, they can easily schedule fittings and haircuts.   

Men who personally know their barber and tailor are sure to get the best service, even when they have to squeeze in appointments at the last minute.

Rule 20: Don’t Wear Something That’s Not Comfortable

Outfits are an extension of men’s personality and lifestyle. When guys wear clothes they pick out themselves, they won’t feel self-conscious as they walk in a lobby full of people. 

Every man’s wardrobe should be filled with clothes they are comfortable wearing. This way, they won’t have a hard time choosing what to wear on a busy morning. When men look in front of the mirror, they should see a reflection of their distinct style that is not thoroughly dictated by passing trends.  

And Don’t Forget to Show Confidence

Every man is guilty of fashion mishaps. Passing trends are enough to make any guy’s head spin. It can take a while to get dressing well. But with a lot of perseverance and a few trips to the local department store, men will be nailing their look, from head to toe, in no time. 

Many men are shy to dress better because they are afraid others will think they are trying too hard. However, while some men may already have the most expensive suits or the best jeans, these things are worth nothing if they don’t exude confidence. 

When men have mastered the art of walking with their chin up and their shoulders back to show off their outfits, they will crush their self-doubt, and people will look at them in a brand new light.

Confidence, coupled with the rules listed above, will ensure that you master your looks and start becoming a fashion icon.