Key Highlights

Elevate your style game with these 10 habits of impeccably dressed men.

  • Prioritize Timeless Style: Choose enduring style over passing trends for a sophisticated look.

  • Simplicity Reigns: Opt for timeless classics and understated elegance for a sharper appearance.

  • Invest in Quality Footwear: Quality shoes and proper maintenance are essential for a polished look.

  • Tailoring Matters: Ensure a perfect fit with alterations from a reliable tailor.

  • Comfort with Style: Balance comfort and style without resorting to overly casual 'comfort clothing'.

  • Smart Shopping: Invest in high-quality, timeless pieces over fleeting trends.

  • Care for Your Clothes: Proper maintenance preserves the integrity of your wardrobe.

  • Understand Fashion Guidelines: Interpret rules creatively to express your individuality.

  • Develop Your Style: Cultivate a unique style that reflects your personality and preferences.

  • Confidence is Key: Wear your clothes with confidence for a lasting impression.

May 09, 2022

10 Style Secrets of Impeccably Dressed Men

With a few tips from the pros, upping your style game is easier than you think.

Have you ever noticed how some men have an effortless way with style? Whether they wear a relaxed jeans and T-shirt combo, winter layers, or a razor-sharp suit, everything looks impeccably well-fitted yet comfortable, nonchalant yet considered.

While there are no guaranteed formulas for sartorial success, adopting some of the habits of the most stylish men can help you avoid fashion faux pas. By emulating these habits, either wholly or in part, you can elevate your style to new heights.

Habit 1: Value Style Over Fashion

"Trends come and go, but style will endure." — Yves Saint Laurent

The most stylish men prioritize timeless style over fleeting fashion trends. This approach keeps them looking current without appearing overly trendy. Trends change rapidly, and trying to keep up can be both financially draining and exhausting, often leading to potential ridicule.

This doesn't mean you should never follow trends, but before investing in the latest fashion, consider three key questions: Am I buying this because I genuinely like it, or just because it's trendy? Does it truly look good on me? Is this a wise purchase that will still look great in six months?

Remember the wise words of Yves Saint Laurent: “Fashions fade; style is eternal.” Prioritizing enduring style over passing trends ensures a more sophisticated and lasting appearance.

Habit 2: Realize That Less Is Often More

Simplicity is king when it comes to men’s style, and this principle applies to almost every item of clothing.

Jeans? A pair of dark, slim-fitting denim jeans outshines distressed or acid-washed options every time.

T-shirts? Icons like James Dean, Marlon Brando, Ryan Gosling, and George Clooney all embrace the timeless appeal of a plain crewneck T-shirt.

Suits? A tartan check three-piece may grab attention, but for the right reasons? Likely not. Regardless of your size or fit, you'll generally look sharper in a well-tailored navy two-piece with a crisp white shirt than in a flashy suit meant only to stand out.

Never underestimate simplicity. If in doubt, choose timeless classics that whisper rather than shout. Confident men don’t need to broadcast brand names or wear flashy logos. Instead, they opt for understated elegance that speaks volumes.

Habit 3: Know the Power of Smart Footwear

Shoes are one of the first things people notice, so every sartorially-savvy man must give footwear the respect it deserves.

Worn-out shoes can ruin an otherwise impeccable outfit, no matter how smart or expensive the rest of it is. Investing a bit more in high-quality footwear is crucial. As Hardy Amies aptly said, “It’s impossible to be well-dressed in cheap shoes.”

Smart footwear starts with purchasing quality shoes but extends to their maintenance. Regular polishing and proper care will keep your shoes looking as good as new over time.

For daily care, wipe your leather shoes with a damp cloth to remove dirt and dust. On weekends, spend 5 to 10 minutes polishing your business footwear to keep them in top condition for the week ahead. Consistent care ensures your shoes complement your style perfectly.

Habit 4: Get Acquainted with a Great Tailor

Knowing a tailor doesn't mean you need bespoke suits; it can be a local seamstress, alterations service, or even a dry cleaner who can adjust the hem of your trousers or take in your jacket. The key is that every well-dressed man understands the importance of a great fit and has someone reliable to help achieve it.

Alterations offer form-enhancing benefits and are often inexpensive. Some services, like Louis Copeland, even offer free alterations years after the purchase. Whether adjusting a new item or modifying an existing piece to accommodate weight changes, smart alterations ensure your clothing fits perfectly.

There's an old saying that an inch is a mile in menswear, and it's true. Every well-dressed man needs a go-to person for adjustments to achieve that impeccable fit.

Habit 5: Know the Difference Between Clothes That Are Comfortable and ‘Comfort Clothing’

Every stylish man wears clothing that he is comfortable in, which translates into visual success. If you feel comfortable in an outfit, it's likely because you are familiar with that style and know it looks good on you.

Playing it safe might seem boring, but it’s much better to wear outfits you feel comfortable and confident in, rather than forcing yourself into something trendy that doesn't suit you.

However, don’t confuse comfortable clothing with ‘comfort clothing’. While fleece tops, hoodies, and track pants might be cozy, they don’t belong in a well-dressed man’s regular wardrobe. Prioritize comfort without sacrificing style.

Habit 6: Know How to Buy Smartly

Stylish men have mastered the art of clothes shopping, and there's more to it than meets the eye.

Smart shopping means investing in key fashion items that transcend seasonal trends. While it’s fun to dabble in the latest fashions, a stylish man’s wardrobe isn't filled with pieces that quickly become passé. Instead, he acquires timeless classics: dark denims, a camel trench, a fitted navy blazer, a crisp white Oxford shirt, a cashmere crewneck, and leather Derby shoes.

Understanding the link between value and quality is crucial. Investing in high-quality classics pays off in the long run. While cheap shoes might seem like a bargain, they won't last and will need frequent replacing. A more expensive pair will endure, making them a smart investment.

Remember: occasionally spend on transitional items, but allocate most of your budget to high-quality menswear classics. These items will look great on their own and allow you to incorporate trends subtly and sophisticatedly.

Habit 7: Know How to Care for Clothing

Buying covetable clothing and putting complementary looks together are essential for sartorial success, but the maintenance and care of clothing are equally crucial for any self-respecting gent.

The best-dressed men know how to keep their clothing in pristine condition, whether it's storing them properly (wooden hangers are recommended) or knowing how best to wash them.

Attention to detail makes all the difference – from having dress shirts dry-cleaned and pressed to folding cable knit sweaters loosely to maintain their shape.

Keeping clothes in tip-top condition preserves their integrity, extends their life, and ensures they look smart and presentable. After all, what's the point of having a timeless capsule wardrobe if you don't know how to care for your clothes properly?

Habit 8: Understand That Few Rules Cannot Be Bent (or Even Broken)

Many men are familiar with common fashion "rules" regarding trouser length, shoe choices with a navy suit, or the bottom button on a jacket. However, it's crucial to understand that these rules are mostly guidelines.

While following rules meticulously might result in a well-dressed but dull world, true style emerges when a man interprets these rules in his unique way. While pairing hiking boots with a three-piece suit might be extreme, bending or even breaking the occasional rule can showcase individuality and creativity.

Habit 9: Cultivate Your Authentic Personal Style

Even the most stylish men draw inspiration from others, but they never simply replicate another man’s look. While imitation may seem flattering, it ultimately reveals a lack of confidence in one’s own style.

Developing a strong personal style is challenging yet immensely rewarding. It's tempting to admire and mimic a colleague or celebrity's outfit, but you'll never truly feel like yourself when you wear it.

True style lies in understanding what suits your features, enabling you to adapt trends, colors, and silhouettes in classic ways that reflect your unique personality and preferences.

Habit 10: Embrace Confidence as Your Ultimate Style Statement

As the old adage goes, ‘Clothing maketh the man’, but nothing is less attractive than a man who appears to be trying too hard. Style is synonymous with confidence; a confident man owns his look because it's an authentic expression of his personality and identity.

Regardless of the occasion, the most stylish men always ensure that they wear the clothing, not the other way around. Confidence is the ultimate accessory that elevates any outfit and leaves a lasting impression.