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Dressing Well: 15 Rules Every Man Should Know

CEO Tinh Phung
Dressing well is an art form that every man should master. While there are no hard and fast rules, there are some valuable guidelines that can help you navigate the world of fashion with confidence....

Dressing well is an art form that every man should master. While there are no hard and fast rules, there are some valuable guidelines that can help you navigate the world of fashion with confidence. These dressing tips for men have stood the test of time and can serve as a failsafe guide on how to dress well in any situation.

1. Wear A Suit Well

The key to a good suit is the fit. Whether buying off-the-rack or opting for bespoke, focus on the fit across the shoulders. Adjustments to the chest and waist are relatively easy, according to Davide Taub, head of bespoke suits at Savile Row tailor Gieves & Hawkes. Stick to classic styles that are versatile and moderate in details. Remember, it's the way you wear the suit that impresses, not the label inside.

man dressed well wearing a suit Image Source: Mr. Katin

2. Invest Wisely In A Watch

A watch is more than just a timekeeping device; it's a statement of personal style. Choose a watch that you love, not just for its potential investment value. Consider functionality and opt for a size and depth that suits your wrist. Aesthetic, functional, and rugged sports models are versatile options that can complement any outfit.

well dressed man wearing a watch Image Source: Monofore

3. Embrace Color

Don't be afraid to add a pop of color to your wardrobe. Most men tend to stick to safe, neutral colors like navy and grey, but color can be timeless too. Experiment with shades like green, pink, mustard, and brighter blues. However, remember that less is more when it comes to color. One garment with a splash of color is all you need to liven up your entire outfit.

back view of a man in denim clothing Image Source: Luca Faloni

4. Wear In Your Jeans Until They Are Yours

When it comes to jeans, the slim-tapered cut is the most versatile and flattering option. It provides comfort in the thigh and works well with both smart shoes and sneakers. Opt for dark, raw denim that ages with you and avoid pre-distressed jeans. The aging process of denim is part of its charm, so embrace it.

Man standing in front of mirror in white shirt buttoning cuffs Image Source: View More Styles on Asket

5. Look After Your Appearance

Investing in quality clothing is only half the battle. Ensure you take care of your clothes to make them last. Use wooden hangers for shirts, shoe trees for your shoes, and have your suits dry-cleaned and pressed. Wash your clothes regularly and avoid tumble drying to preserve the fabric. Attention to grooming is equally important. Establish a simple grooming regime, and pay attention to the details that can make a difference.

Man walking across the street Image Source: Unsplash

6. Keep Your Underwear Simple

When it comes to underwear, simplicity is key. Avoid novelty prints and heavily-branded designs. Opt for cotton boxer shorts or boxer briefs that are comfortable, breathable, and take repeated washing well. Your underwear is not the place to express your 'personality'; instead, let it provide a solid foundation for your outfit.

man wearing yellow suit with red striped tie Image Source: CDLP

7. Spend Money On Shoes

Invest in quality shoes that stand the test of time. Classic designs with simple lines are timeless. Opt for re-soleable Goodyear welted shoes that can last 15 years or more. Pay attention to the shape of the toe, as round toes are always in fashion. Avoid pointy or square toes, as they can look impractical.

man adjusting his collar with chic watch on wrist Image Source: View More Styles on Myrqvist

8. Keep Accessorizing To A Minimum

Accessories like ties and pocket squares add individuality to your outfit, but be careful not to overdo it. Harmonize them with your clothing by selecting colors that complement each other. Avoid matching them too precisely. When curating shirt and tie combinations, wear a tie or pocket square in a darker shade than your jacket. Remember, less is more when it comes to accessories.

how to dress well for different settings with men and women at a disco party Image Source: Drake's

9. Know Thyself

Style is not about conforming to someone else's standards; it's about expressing your true self. Dress in a way that reflects who you are and makes you feel comfortable. Genuine style icons are those who have the confidence to be themselves and make their clothes an extension of their identity.

man wearing Warby Parker glasses Image Source: Warby Parker

10. Dress For The Setting

Dressing well is not just about self-expression; it's also about showing respect for the occasion and those around you. Dress appropriately for your environment, whether it's a formal dinner or a casual outing. When in doubt, it's better to overdress than underdress. Remember, style is about feeling comfortable in your own skin.

man wearing denim jacket Image Source: Unsplash

11. Don't Skimp On Glasses

Choose your glasses carefully, as they can define your look for years to come. Take the time to find frames that suit your face shape and eyebrow shape. Consider your hairstyle as well. While it's tempting to go for cheap frames and expensive lenses, invest in quality frames that will last. Remember, your glasses should enhance your style, not detract from it.

man wearing a tuxedo Image Source: Warby Parker

12. Choose Versatile Outerwear

Modern technical fabrics offer lightweight and breathable outerwear options that are both stylish and functional. Opt for easy cuts and darker shades that can be worn in various settings. A field or bomber jacket is a versatile choice, while a short mac is perfect for dressing up.

multicolored ties for men Image Source: Percival Menswear

13. Buy A Dinner Suit, Never Hire

Invest in a dinner suit that fits you perfectly instead of renting one. Hiring can lead to ill-fitting and boxy ensembles. Own a classic dinner suit in midnight blue with satin lapels and trousers seams. Knowing how to tie a bow-tie yourself is essential. A well-fitted dinner suit exudes elegance and ensures you're always ready for formal occasions.

How To Dress Well: The 15 Rules All Men Should Learn Image Source: How To Dress Well

14. Stick To Classic Shirts

A well-pressed shirt can make any man look polished and put together. Avoid bold and extravagant styles unless you can carry them off. Opt for a semi-cutaway collar that works with or without a tie and sits properly under a jacket. A classic, well-maintained shirt never goes out of style.

How To Dress Well: The 15 Rules All Men Should Learn Image Source: L'Estrange London

15. Know When To Break The Rules

While guidelines are helpful, don't be afraid to break the rules from time to time. Fashion is constantly evolving, and style advances by challenging norms and embracing innovation. Feel free to experiment and make your own fashion statements. Enjoy the freedom to make mistakes and discover your personal style.

How To Dress Well: The 15 Rules All Men Should Learn Image Source: How To Dress Well