Men’s fashion tips: The 16 essential rules every well-dressed man should know
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what every man should know to ensure he's always the best dressed in the room.
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.
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
2. Invest in quality
3. Fit over fashion
5. English for quality, Italian for flare
6. The devil is in the details
7. Start with basics – build with staples
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
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 2024.
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