HOW TO DRESS WELL: The 15 Rules All Men Should Learn  

Life is full of rules. However, some rules can be helpful. As with the rules for how to dress well. Each person has a different opinion. 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 is becoming ever more diverse, experimental, and plentiful, making it difficult to know where to turn in times of doubt and confusion.

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 on 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 dressing today.

WEAR A SUIT WELL

Fit is the key to making a suit look good. Davide Taub is the head of the bespoke suit at Savile Row tailor Gieves & Hawkes. He says that if you buy off the peg, it’s important to focus on the fit across your shoulders. He cautions against wearing a period suit unless your goal is to create a unique look. Classic is the best and most practical – dark, single-breasted, with two buttons and moderate details. It’s not boring. A suit is a uniform. This suit can be viewed as a blank canvas to create different ideas about individuality. It is the way you wear it that impresses, not the label.

INVEST WISELY IN A WATCH

Don Cochrane is the managing director of the British watch brand Vertex. Choosing a watch you love is important, not just because it may make you money. Watches mark your passage through the years. You also need to be practical.” Functional, stylish, and rugged sports watches can withstand everyday wear. But a watch must fit you. You should find it comfortable and the right size and depth for your wrist. 40mm is the ideal size.

DON’T CHANGE YOUR COLOUR

You can have a little colour in your casual wear or formal wear. Oliver Spencer, a menswear designer, says that most men are afraid of colour. They’re scared by any colour other than navy and grey. But colour can also be timeless. A green suit can look especially rakish. Spencer recommends brighter, more versatile shades of blue that can lift any outfit year-round. He says that you only need a little bit of colour in one outfit.

WEAR YOUR JEANS UNLESS THEY ARE YOURS

According to Alex Mir (co-owner of the Sheffield-based label Forge Denim), the most versatile cut of the beloved garment is slimly tapered’. He advises that the slim-tapered cut is more comfortable in the thigh and can be worn with smart shoes or sneakers. It’s the perfect year-round, wear-with-anything, dress down or up style.” The wise will also wear dark, raw denim and give the pre-distressed an extended berth. The beauty of denim is its ability to age with your style. This is a great opportunity!

LOOK AT YOUR APPEARANCE

This is the advice that your mother may give you, but it’s something you should do if your clothes are expensive and well-maintained. Wooden hangers are best for shirts, and wooden shoe trees are the finest shoes. You should also dry-clean, press your suit, and wash your clothes frequently. Avoid tumble drying your clothes as it can damage the fabric. Finally, polish your shoes. You must care for your leather jacket and the leather 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.

KEEP YOUR UNDERWEAR SIMPLE

Style is not what everyone else sees. Two rules apply to men’s underwear. One, novelty prints should not be worn by grown men. Underwear is not the right place to express your “personality”, as shirt-maker Emma Willis points out. 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.

SHOES ARE A CHOICE

Tim Little, the owner of Grenson, believes that simplicity is key to timelessness. You don’t want the sole, colour, 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-solvable Goodyear Welted models are the best. Brogues, loafers or plain, dark five-eyelet Derm with a round-toe last are classic options. But don’t forget to look for quality dress socks. Little says that the shape and style of your toes matter most. It’s square or pointy toes that are most practical. No one has feet like that.

KEEP ACCESSORIZING TO MINIMUM

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, says it’s possible even to juxtapose them. You don’t want to match them up. When curating shirt-tie combinations, make sure your tie and pocket square is darker than your jacket. Don’t overload on accessories – if you are unsure, keep it simple and remove one. Hill says, “You want to exude a sense of calm and ease.” “You only need one point to be interested.”

KNOW YOURSELF

A man who dresses according to his opinion of 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 show that independent and confident people in their choices have a clothing second skin.

DESS FOR THE SETTING

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? According to one of Tom Ford’s fashion quotes, it’s not conformity. This is a sign of respect for others. It’s about being comfortable with yourself. Overdress when in doubt.

GLASSES ARE NOT TO BE OVERPRICED

Spend time looking for the perfect glasses. According to Tom Davies, an eyewear designer, “People spend on average seven minutes choosing a pair that will be defining them for the next three years or more.” Poor fit and poor choice are why so many people hate glasses. Davies advises that you should not buy cheap glasses and be sold expensive lenses. The frames will soon look worn out.

CHOOSE VERSATILE OUTERWEAR

Although it may be tempting to stick with a traditional style, modern technical fabrics in darker colours and simple cuts make coats lighter and more breathable. Adam Cameron, owner and designer of The Worker’s Club, says that heavy wool coats are becoming less practical due to seasons, climate, and purchasing habits. Consider a coat as your final layer. You can dress up or down as needed.

Buy a DINNER SUIT and NEVER HIRE

Even though formal occasions are rare, they are all the more important. It may seem like an extravagant expense, but owning a dinner suit that fits you better than hiring one is more practical after many years of regular use. Toby Lamb, a designer of contemporary tailoring label Richard James, warns that hiring can make the wearer look almost childlike if they are wearing an oversized, boxy outfit. A classic dinner suit is single-breasted in midnight blue with satin lapels. The trousers have seams. You must learn how to tie a bow tie.

STICK TO THE CLASSICS WITH SHIRTS

James Cook, Head of Customized shirtmaking for Turnbull & Asser, says, “It seems silly, but any men’s shirt can look expensive if well-pressed.” Cook is also very particular about the details. He recommends that you strike a middle line. Avoid bold styles unless it is something you are comfortable with. A semi-cutaway collar will work well under a jacket and can be worn with or without a tie.

KNOW HOW TO BREAK THE RULES

Know when to follow black tie dress codes and let them go. Many are there because the occasion or your boss requires them. Drakes’ Hill also notes that rules can be too rigid, and it’s possible to rip them up. This is how fashion evolves, slowly and surely. Enjoy the freedom to make mistakes.

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