man in black dress shirt wearing black sunglasses

How to dress well: 10 fashion rules for men

man in black dress shirt wearing black sunglasses

KEEP YOUR UNDERWEAR SIMPLE

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.

SHOES ARE A CHOICE

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 gold standard. They should last for at least 15 years. Brogues, loafers and plain dark five-eyelet Derbys with a round-toe last are classic styles. However, quality dress socks are also available. Little says that it’s the shape and style of the toe that matters most. Round never goes out fashion. It’s square or pointy toes that are most practical.

KEEP ACCESSORISING TO A 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, 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 and pocket square are 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.”

KNOW YOURSELF

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 way and have a confidence that clothes are not just a garment, but a second skin.

DRESS 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. It’s not conformity, according to one of Tom Ford’s most famous fashion quotes. It’s about being comfortable with yourself. Overdress when in doubt.

GLASSES ARE NOT TO BE SKILLED

Spend time looking for the perfect glasses. Tom Davies, an eyewear designer, says that people spend on average seven minutes choosing the right pair of glasses. Poor fit and poor choice are the main reasons so many people hate their 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 colors and simple cuts are making coats light and breathable while still protecting your skin. Adam Cameron, owner and designer of The Workers’ Club, says that heavy wool coats are becoming less practical due to changes in the weather, buying habits, and seasonality. Consider a coat as your final layer. You can dress up or down with a jacket or field jacket.

BUY THE DINNER SUIT AND NEVER RENT

Even though formal occasions are rare, they’re more common than you might think. It may seem like an extravagant expense, but owning a dinner dress that fits you is more practical than hiring one. Toby Lamb, the design director at Richard James contemporary tailoring label, warns that hiring can make the wearer look almost childlike if they are wearing an oversized, boxy outfit. A classic dinner suit is one that’s single-breasted in midnight blue with satin lapels. It is important to learn how to tie your bow-tie also.

STICK TO THE CLASSICS WITH SHIRTS

James Cook, Turnbull’s head of bespoke shirtmaking, says “It seems silly.” Asser said, “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

You should know when to follow dress codes like black tie and when to let them go. They are usually there because they are required by the occasion or because someone higher up – like your boss – expects 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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