Dressing well can be challenging, as everyone has their own personal style and preferences. However, some rules can be helpful in guiding men on how to dress well. These tips are often based on history and proven to work for generations, focusing on fit, quality, versatility, value, and avoiding extremes. While these may not be the only rules, they can act as a solid foundation for men to build their personal style upon. Ultimately, the pleasure of clothing comes from experimenting and discovering what works for you.
1. WEAR A SUIT WELL
To wear a suit well, focus on the fit across the shoulders. Classic styles such as dark, two-button, single-breasted, and moderate in details are best. Remember that a suit is a uniform, and it's the way you wear it, not the label, that impresses.
2. INVEST WISELY IN A WATCH
Invest wisely in a watch by choosing one you love, not just one that might make money. Aesthetic, functional, rugged sports models are versatile and can withstand everyday wear. Make sure the watch feels comfortable and is the right size and depth for your wrist, with 40mm considered the ideal size.
3. COLOR IS YOUR FRIEND
When it comes to fashion, don't be afraid to add a pop of color to your wardrobe. Menswear designer Oliver Spencer believes that many men shy away from color because they are intimidated by anything that isn't navy or grey, but color can be just as timeless and versatile as those neutral shades. A green suit, for example, can give off a rakish and dashing vibe, while other shades such as pinks, greens, mustard and brighter blues can add a fresh and modern touch to any outfit. However, it's important to keep in mind that less is more when it comes to color. A small pop of color, such as a bright tie or pocket square, can make a big impact.
4. YOUR JEANS SHOULD BECOME AN EXTENSION OF YOU
Jeans are a staple in any man's wardrobe, and finding the right pair can make all the difference. Alex Mir, co-owner of Sheffield-based label Forge Denim, believes that the most versatile and useful cut of jeans is the slim-tapered. This style is wider in the thigh for comfort, but narrows at the ankle, making it suitable for both dressy and casual occasions. Mir also suggests opting for raw, dark denim instead of pre-distressed denim. The beauty of denim is that it becomes unique and personal to you as it ages and wears in with your lifestyle.
5. TAKE CARE OF YOUR APPEARANCE
It may sound like basic advice, but if you've invested in quality clothing, it's important to take care of it. This means using wooden hangers for shirts and shoe trees for shoes, keeping your suit pressed and clean, washing your clothes regularly, and polishing your shoes. Additionally, don't forget about the little details of personal grooming, such as brushing your hair and cutting your nails. After all, the devil is in the details and a well-groomed appearance can make all the difference.
6.KEEP YOUR UNDERWEAR SIMPLE
When it comes to men's underwear, there are two main rules to follow. Firstly, novelty prints are not suitable for grown men. Your underwear is not the place to express your personality, according to shirt and underwear-maker Emma Willis. Secondly, heavily-branded underwear lacks sophistication. Of all places where you might have the confidence not to have branding, your underwear should be it, adds Willis. The best type of underwear is the cotton boxer short or boxer brief, as they are comfortable against your skin, breathe well, and can withstand repeated washing.
7. SPEND MONEY ON SHOES
"Timelessness is about simple design and all the more so with shoes," says Tim Little, owner of heritage shoe brand Grenson. "The color, the pattern, the sole - you don't want it fussy. Anything fussy may look good now but will look strange very quickly." Quality shoes, such as re-soleable Goodyear welted examples, are an investment that should last 15 years or more. Opt for classic styles, such as The Loafer from Amberjack or classic brogues, loafers, or a plain, dark, five-eyelet Derby on a round-toe last. Don't forget to find quality dress socks as well. "It's the shape of the toe that really counts - and round never goes out of fashion," says Little. "It's pointy toes or square toes that look obviously impractical. Nobody has feet shaped like that."
8. KEEP ACCESSORISING TO A MINIMUM
Accessories, such as ties and pocket squares, bring individuality to classic clothing, but it's important to be careful how you use them. "It's best to harmonize them with what you're wearing by picking out a color or two. Or even to juxtapose them entirely," says Michael Hill, creative director of men's accessories brand Drake's. "What you don't want is to match them up." When it comes to curating shirt and tie combinations, wear your tie or pocket square in a darker shade than your jacket. And don't overdo the accessories - if in doubt, think less is more and take one element away. "You're aiming for an air of nonchalance," adds Hill. "You just need one point of interest."
9. KNOW THYSELF
There's nothing less stylish than a man dressed as he thinks he should dress, rather than in what he genuinely feels suits who he is. Of course, there are exceptions - there are no prizes for dressing like a rodeo clown unless indeed you are one. But whatever you're wearing, you have to own it. Genuine style icons are those who go their own way with a self-confidence that comes from their clothes being a second skin, not a costume.
10. DRESS FOR THE SETTING
Style is not only about self-expression; it's also about being dressed appropriately for your environment. Think of clothes as codes: you need the right combination to work with the setting you're in - whether it's a formal dinner or a lazy Sunday in the pub. The worst style is one which is out of place. Is this a kind of conformity? No, as one of Tom Ford's oft-trotted out fashion quotes explains, it's a mark of respect for others and about feeling comfortable in yourself. When in doubt, overdress.
11. DON'T SKIP ON GLASSES
Invest time into finding the right spectacles for you. "People spend an average of seven minutes picking a pair that will define them for the next three or more years," notes eyewear designer Tom
12. CHOOSE FLEXABLE OUTERWEAR
When it comes to outerwear, versatility is key. Rather than opting for a classic style, consider modern technical fabrics in darker shades and easy cuts that are lightweight and breathable, yet still provide proper protection. As the owner of outerwear specialist The Workers’ Club, Adam Cameron suggests, "Think of a coat instead as being your final layer – one you can wear as much or as little under as required." A field or bomber jacket is a great all-rounder, but for a more dressed-up look, consider a short mac.
13. BUY A DINNER SUIT Another important investment for any man's wardrobe is a dinner suit. While formal occasions may be rare, owning a suit that fits you rather than hiring one makes more sense in the long run. As Toby Lamb, design director of contemporary tailoring label Richard James warns, "With hiring, there’s always the risk of the wearer looking almost childlike while dressed in some oversized, boxy ensemble." To ensure a timeless and classic look, opt for a midnight blue, single-breasted, with satin lapels and trousers seams and make sure to learn how to tie a bow-tie yourself.
14. YOU CANT GO WRONG WITH CLASSIC SHIRTS
When it comes to shirts, sticking to the classics is always a safe bet. As James Cook, head of bespoke shirtmaking for Turnbull & Asser states, "any men’s shirt can be made to look expensive if it’s well-pressed." However, Cook also emphasizes the importance of paying attention to details. To achieve a sophisticated look, avoid bold styles unless you feel confident in carrying them off and opt for a semi-cutaway collar that works with or without a tie and sits properly under a jacket.
15. KNOW HOW TO BREAK THE RULES
While it's important to adhere to dress codes for certain occasions, it's also crucial to know when it's appropriate to break the rules. As L’Estrange London's Drakes' Hill notes, "we can get too hung up about rules as well, and there’s always a case for ripping them up." Style is constantly evolving and it's important to enjoy the freedom to experiment and make mistakes.
In summary, when building a timeless and sophisticated wardrobe, it's important to invest in versatile outerwear, a well-fitted dinner suit, classic shirts and to strike a balance between adhering to dress codes and breaking the rules to stay current and stylish.
