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15 Dressing Rules All Men Should Learn

black and orange nike polo shirt

Life is full of rules. However, there are some rules that can be helpful. As with the rules for how to dress well. Each person has a different opinion and each individual’s experience will vary. Or, what works for one person may be considered too simple or too avant-garde for another. When it comes to dressing, they must be taken at their face value. These are solid suggestions, not the final word in style.

Good advice is not to be taken lightly. Menswear becomes more diverse, experimental, and abundant. In times of doubt and confusion, it can help to have a fall-back position that cuts through all the noise.

These “rules” are often rooted in history. They have worked well for generations and can be expected to continue to work today. They tend to be based in the obvious, so they are often overlooked. A preference for good fit and high quality, versatility.

There are many more rules than the ones presented here. You may already have some of these rules. This is all part of the joy of clothing. These rules are reliable and can be used together to guide you on how to dress today.


Fit is the key to making a suit look good. Davide Taub is the head of bespoke suits at Savile Row tailor Gieves & Hawkes. He says to be cautious when wearing a period-style suit, unless you are trying to achieve a complete period look. “In isolation, the suit can look like a novelty.” Classic is the best and most practical – dark, single-breasted, with two buttons, moderate details. It’s not boring. A suit is an uniform. This suit can be viewed as a blank canvas on which to create different ideas about individuality. It is the way you wear it that impresses, not the label.

A suit makes a man look good.


Don Cochrane is the managing director of British watch brand Vertex. He says that a watch is like an art piece. It is important to choose a watch you love, and not just because it may make you money. Your time is personal and watches are personal. You also need to be practical. Functional, aesthetic, and rugged sports models can go with everything and withstand the daily wear. But a watch must fit you. You should find it comfortable, and the right size and depth for your wrist. 40mm is considered to be the “Goldilocks” size.

A watch is a well-dressed accessory for a well-dressed man.


You can have a little bit of colour on formalwear and casual wear. Oliver Spencer, a menswear designer, says that most men are afraid of colour. “They feel intimidated by any other than navy and grey. But colour can also be timeless.” Spencer says that a green suit can look especially rakish. He also suggests using brighter colors year round, such as pinks, greens and mustard. He says that you only need a little bit of colour in one outfit.


According to Alex Mir, coowner of Sheffield’s label Forge Denim the most versatile cut of the most beloved garment is the ‘slim-tapered. He advises that the slim-tapered cut is wider at the thigh so it’s more comfortable. However, it is narrower so it can be worn with smart shoes or sneakers. It’s an all-year-round favorite, you can wear it with anything, and the smart will also wear dark, raw denim, giving the pre-distressed a wider berth. The whole point of denim is its ability to age with how you wear it. This is a great opportunity!


If your clothes are expensive and well-maintained, take care of them. For your finest shoes, use wooden hangers and shoe trees. Dry-clean your suit and press it. Wash your clothes frequently and don’t tumble dry (it can cause fabric to shrink). Polish your shoes. You must also care for your leather jacket and the shoes you wear every day. You should have a simple but effective grooming routine. Brush your hair, cut your nails, and that’s it. The devil is in the details.


Style is not what everyone else sees. There are two rules when it comes to men’s underwear. One, novelty prints should not be worn by grown men. Emma Willis, shirt and underwear maker, points out that “your underwear does not have the right place to express your personality.” Two, heavily branded underwear lacks sophistication. Willis adds, “Of all the places you might be able to not have branding, it should be your underwear.” The cotton boxer short is the style that has stood the longest. This is likely because, as with linen, they can be washed repeatedly, are easy to breathe, and feel great against your skin.


Tim Little, the owner of Grenson heritage shoe brand, says that simplicity is key to timelessness. You don’t want the sole, color, or pattern to be fussy. While it may look great now, anything too fussy will soon look out of place. Quality shoes are the best investment. Re-soleable Goodyear Welted models are the best. They should last for at least 15 years. Brogues, loafers and plain dark five-eyelet Derbys with a round-toe last are classics. But don’t forget to invest in quality dress socks. Little says that it’s the shape and style of the toes that matter most. Round never goes out fashion. It’s square or pointy toes that are most practical. No one has feet like that.”


Accessories such as ties and pocket squares add individuality to traditional clothing. But be careful about how you use them. It’s best to match them with your clothing by choosing a few colours. Michael Hill, the creative director at Drake’s men’s accessories brand, suggests that you can even juxtapose them. You don’t want to match them up. When you are coordinating shirt and tie, make sure your tie or pocket square is darker than your jacket. Don’t overload on accessories – if you are unsure, reduce the number of pieces and remove one. Hill says, “You want to exude a sense of calm and ease.” “You only need one point to be interested.”


A man who dresses according to his opinion of what is fashionable, rather than wearing what he feels best suits him, is less elegant than anyone. However, there are some caveats. You don’t get any prizes for dressing up as a rodeo clown unless you are one. You must own what you wear. True style icons are those who make their own style and have a confidence that clothes are not just a garment, but a second skin.


Style is more than self-expression. It’s about dressing appropriately for your surroundings. Consider clothes like codes. You need the right clothing to match the environment. A style that is not in place is the worst. This is a form of conformity? It’s not conformity, according to one of Tom Ford’s most famous fashion quotes. It’s about being comfortable with yourself.

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