Men’s fashion tips: The 16 essential rules every well-dressed man should know

Style is a bit of a Rorschach test. It can tell people around us who we are and what we think of ourselves. It can tell people more than we think. Some of us are mavericks, shirking the rules and subverting expectations at every turn, simply because we don’t like to be put in boxes. Other groups of us like rules and we want the comfort that order and uniformity bring us. Then, even more of us are somewhere in the middle when it comes to men’s style and crave order and uniformity to allow us to find our boundaries, only to shirk them later when we want to feel free. Men’s fashion offers us all of the above. While some rules are made to be broken, others are tried-and-true staples to live on.

Rules vs. guidelines and how to break them

Never mix black and brown. Don’t wear black dress shoes with a navy suit. Ditch the graphic tee. These are considered “rules of menswear,” but they are more of guidelines. They help you look great while you learn what your style is or how to put together an outfit. Once you figure out how to do that, these rules tend to get in the way of evolving your style to be truly unique. The first thing you need to know if you’re looking to revamp or upgrade your wardrobe is that guidelines can be adjusted, deviated from, or flat-out ignored. Rules, however, should be followed whenever possible. Don’t worry; we took the time to collect the rules you should always follow in men’s style.

These tips will help you define your style, find your archetype in men’s fashion, and even help you navigate men’s clothing without losing your mind at the ever-changing landscape that is men’s apparel. Once you learn these, you will have a framework to start branching out and breaking the rules, becoming a maverick of style all your own.

1. Emulate, don’t impersonate

We all have those men that we look to for style inspiration. Whether it is David Beckham, Ryan Reynolds, or Dwayne Johnson, some of the best-dressed celebrities can determine the course of fashion in menswear. The trap we can fall into when we take inspiration from celebrities is that we impersonate them instead of emulating them.

The reason this doesn’t work, outside of creating the look of a lack of originality, is that what works for David Beckham won’t necessarily work for you. Not only is that going to cause immense frustration when you put something on that looked great in the magazine but not in the mirror, but these people employ stylists and a rather large bank account to ensure they look that good. Instead, if you like how Beckham wears T-shirts and denim, find a great denim brand within your budget and the right T-shirt for your lifestyle. Don’t copy their clothes; copy their approach.

2. Invest in quality

Whether you are buying suits, denim, shoes, or a hat, you can choose between spending very little money on something that will do for now or dropping more on something that will do for years to come. While it may seem more practical to go the cheap route and save money for something else, you almost always spend more in the long run because the cheap garments break down.

Dropping more money upfront allows you to choose garments that will last. Choosing the kind of garment you can wear for years to come. One of the ways to look at it is how much each wear costs. If you buy a cheap suit for a few hundred dollars, it can break down quickly, causing you to buy a new one sooner. The cost per wear is higher than a high-quality suit you can wear for ten times longer.

3. Fit over fashion

We all want to look good. The retail stores and fashion industry have conditioned us to believe the only way to do that is to wear the latest fashion trends. The truth is that if it doesn’t fit well, it won’t matter. How your garment fits is infinitely more important than whether or not it is the latest fashion. You can have the most up-to-date fashion trends, but if they don’t fit well, you will look extremely outdated.

4. Get chummy with a tailor

Going along with getting the fit right, no one will be more important to your wardrobe than the right tailor. While most people think the only time you need a tailor is if you buy suits, they can actually do work on virtually every article in your closet. Even T-shirts and jeans can benefit from the work of a good tailor.

The critical part of finding the right tailor for you is finding one who knows your body and how to get the best out of your clothes. Unfortunately, that means doing some trial and error. However, once you find the right person, you’ll be surprised how often you take even your most basic garments to be altered.

5. English for quality, Italian for flare

While English tailors and shoemakers aren’t the only ones to excel in the way of quality, they have been the leaders for generations. With brands like George Cleverley and Foster & Son ruling the scenes for over 150 years, there is no shortage of great shoes that will last you for a decade or more. Similarly, the menswear world seems to have begun in London’s Saville Row, where some of the world’s best tailors still reside today.

A little further to the East, Italy houses brands like Giorgio Armani and Dolce & Gabbana. These are the kinds of suits that turn heads the moment you walk into a room and command attention until you leave. While English suits and shoes do have some pizzaz and Italian suits and shoes are no slouch in the quality department, there is an old adage in the menswear industry, if you want something that will last a decade, go English; if you want something that will be remembered for a decade, go Italian.

6. The devil is in the details

An outfit may seem like it is simply a shirt, a pair of pants, and the right pair of shoes, but all of the best looks involve accessories that accentuate the rest of the outfit. Whether it is a necklace, bracelet, hat, or pocket silk tucked into the breast pocket of your suit, the right accessory can completely change your look and offer the finishing touches on an otherwise mediocre outfit.

The trick with accessorizing is subtlety. If you pile up rings or bracelets, you start to appear garish. Remember, it is possible to have too much of a good thing.

7. Start with basics – build with staples

If you think about one of the most emulated style icons in the history of menswear, Mr. James Bond, you’ll notice that he never really wore a lot of flashy items. He wore a lot of basics, but he always did so in luxurious ways.

Instead of spending money on flashy items that will be remembered every time you wear them (limiting the times you can wear them), invest in upscale basics that can be worn more often and layered. Simple solid colors, denim, or chinos will be some of your best items, and you’ll wear them the most. Once you have those, build on your wardrobe by purchasing your staples like brighter colors and patterns.

8. Learn your colors

Like it or not, there will be some colors that you just can’t pull off. No matter how much you love yellow, some pale men are washed out if they try to wear it. One of the ways you can learn the best colors for your skin tone is to do a color analysis. This process involves taking your personal skin tone and evaluating its relationship to colors. Once you know which colors are your strong ones and which ones you need to stay away from, it will make shopping much easier in the future.

Note: This doesn’t mean if you love yellow, but it washes you out — that you can never wear it. It only means that you may need to work harder to pull it off. A different shade. A subtle pop of color. You may have to play with those tougher colors to figure it out.

9. Complement, don’t match

One of the most common mistakes men make when they are picking out accessories or things to go along with their outfits is they try to match instead of complement. If you are wearing a suit and tie, matching a pocket silk with a shirt or a tie can make the whole ensemble look like it came out of a box at Kohl’s. A color complementing it (employing your 9th-grade art class knowledge of the color wheel) will upgrade any ensemble.

Think about complementing your shirts with pants or jackets in a casual outfit. The last thing you want is to look like you’re wearing a tracksuit from 1993. Try lighter or darker shades of the same color or complementary colors on the color wheel to make the look pop.

10. Layer for the weather and for the dress code

Layering is a skill that you will thank us for later. If there is unpredictability in the weather or the dress code, layering items on top of each other that can be peeled off in times of need will be a lifesaver. There are many ways you can accomplish this in a few different scenarios.

Sweaters are going to be your best friend in layering. Putting one under a suit coat but over a dress shirt allows you to go more casual or more formal, depending on the need. If it is a situation where you need to be more formal, you can lose the sweater and simply wear the suit. If it is casual, you can lose the jacket and tie and just wear the sweater and dress shirt.

11. Four-legged stool

The four-legged stool is a tool used in the tailored clothing (suits) community to help men know and understand how to build an adequate suit wardrobe. The importance of having the right suit for when the moment hits is something you don’t fully understand until you’re caught without it. If you learn the process here, it will ensure you always have the suit you need. Remember to stick to the basics, then build on them once you have them all.

12. Sometimes, always, never

This tip is more of a rule to follow. The rule relates to the buttons on your suit coat and helps gentlemen figure out which buttons should be buttoned and which shouldn’t, just for etiquette’s sake. When you wear a suit coat, start at the top button and recite as you move down, “sometimes, always, never.” That means the top button of a three-button suit is sometimes buttoned, the middle is always buttoned (when standing, it is undone when sitting), and the bottom button is always left undone.

The rule also extends to cardigans, vests, and overcoats as well. The tradition goes back to men riding on horses and needing the bottom of their clothing to open so it could lie on each side of the horse.

13. Start with denim, then vary your bottoms

Every man needs to have a great pair of jeans. They will be great for a first date, a weekend barbeque, or a quiet day at home. Leave the light wash on the shelf at first and focus on the darker washes. The dark colors are slimming and are much easier to dress up or down.

Once you have the right pair of jeans, the next step is to find the right pair of chinos. While they come in almost any color you could want, the best color to start with is khaki color. When paired with dark denim, they will both go with nearly anything in your closet.

14. Fill out your shoe wardrobe

There are seven pairs of shoes that every man should own to have a complete essential shoe wardrobe. Once you have acquired all of these, you can start to vary your shoes and have some fun with the ones you buy. While you may be tempted to go with the cheaper options as often as you can in order to get the seven, it will benefit you more to invest in some of the higher-quality options to ensure that you don’t have to continue to replace them.

15. Commit to a skincare routine

A skincare routine is one of the most overlooked aspects of style for men. While we all love the idea of having great skin, most of us don’t take the time to get it. A great routine will involve moisturizer, SPF, and something for bags under the eyes. Even if you like the leathery look of John Wayne, taking care of your skin is the best way to ensure you age gracefully.

16. The right watch will complete every outfit

No matter what you’re doing, there is a watch that will elevate your look. There is a watch for every situation. The pilot watches for the captains of the sky. Dive watches for the explorers of the deep. Field watches for the men who uncover the earth’s secrets. And even tactical watches for the ones who protect us. Investing in the right watch will always be one of the best investments in your wardrobe and will complete any look that you put together.

These 16 rules may be a lot to think about when getting dressed every morning, but once you have them down they will become second nature. If you want to elevate your style, commit yourself to learning each one of these rules and then focus on the guidelines you want to break out of. Go ahead and wear black shoes with navy once you figure out how to pull it off. Find the lighter shades of brown that can look great with black and put together a daring look. But make sure, as you start breaking rules, you keep these rules on the unbreakable list of men’s fashion 2023.

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