Yesterday I had a brief exchange with a group of men about what dressing well truly is, and why should we care about it.
What piqued my attention is that most of them have a vague idea: tailored clothes, clean shoes, grooming on point, were the most common replies on the right meaning of dressing well. The common misconceptions popped up, too: having a big closet, designer labels, expensive items. What piqued my attention is that despite getting the general idea right, they feel lost when creating outfits.
This fifteen minute exchange inspired today’s article.
What is dressing well?
Dressing well goes beyond what you wear. It’s about wearing the right clothes for your body, your complexion, and the context. It’s about expressing yourself and enhancing your self-esteem.
Why should you care?
Because people judge you based on how you present yourself. It’s human nature: we are attracted to beauty and harmony. “But I’ve never heard about appearance issues in corporate, we’ve evolved as a society.” -one of the men said. This is utterly wrong. We didn’t evolve as a society; we stopped being honest about appearance.
The truth is that no HR employee, investor, or business owner will tell you they rejected you because of how you look. And frankly, I cannot judge them. You cannot know when the person you rejected ends up being a lunatic that will call you racist, fatphobic, transphobic, xenophobic, or hatemonger; in a thousand-word rant that might be amplified by some activist group on social media and the press; putting the employee and/or their company through the hell of cancel culture. The HR employee won’t risk his job, nor the investors and companies would lose money because a person is at odds with reality.
Being well-dressed earns admiration and respect. Taking care of yourself implies competence for professional tasks. To be taken seriously and get the opportunities you want, you have to work on your appearance as a man.
How to dress well in every context
“Aren’t dress codes things that rich people enforce so they don’t have tacky people in their events?” Another man asked when I brought up context. In fact, rich people can be tacky (see Hollywood), and dress codes are life savers. They are the unwritten rules of what’s expected of people’s appearance in different contexts, so you avoid looking out of place, or as if you’re trying too hard.
Here’s a quick guide on dress codes for men, so you can make an inventory of your closet and plan your shopping accordingly.
Business Casual: for the everyday professional
Key elements: choose dress pants or chinos you can wear with a button-down shirt. You can incorporate a blazer for an extra touch of formality.
Footwear: leather shoes are best, however if it is not too conservative, clean and modest sneakers are fine.
Styling tips: no t-shirts. Ever. Go for polo shirts instead. Dark jeans are ok if they’re not too casual (no details, not frayed, or bleached). It is important to always maintain a neat and polished appearance.
Smart Casual: where comfort meets flair
Key pieces: fitted trousers or chinos with long-sleeve shirts. For added smartness, throw a blazer on top.
Footwear: dress shoes or fashionable ankle boots are your go-to.
Styling tips: this is where you can show off your personality. It is fine to incorporate soft patterns or colours, just do not overdo it. The accessories should be simple, but attractive.
Business formal: timeless elegance
Key pieces: a dark suit, dress shirt and tie or bow tie are a must.
Footwear: choose Oxfords or brogues for that classic finish.
Styling tips: stick to a strict color palette and pattern. It’s always all about the suit (minus a pocket square here and there).
Cocktail attire: sharp yet social
Key pieces: though you can opt for lighter suits on warmer months, a dark suit and a crisp white shirt are standard.
Footwear: dress shoes – keep them smart, no trainers.
Styling tips: do not wear anything too formal (like bow ties and cufflinks) Sharp is what you should aim for. Now is the time for accessories, but no excesses.
Casual office: effortlessly stylish
Key pieces: well-fitted jeans or chinos, with polos or smart t-shirts do the trick. In the cooler months, you can swap the blazer for a knit cardigan.
Footwear: casual sneakers or loafers can complete the look.
Styling tips: however comfortable you might feel with a casual setting, don’t take it as “anything goes”. Your clothes should be clean, well-cut, and worn with finesse.
By understanding and adapting to these different dress codes, you can navigate through life's different events with confidence and ease. Dressing well is not just about following rules: it's about understanding the language of clothing and using it to express yourself appropriately in any given context. This will cause positive changes in how people perceive you. Would you say this is straightforward? Perhaps -I’ve been helping people dress to win for four years. This knowledge, and wearing your shirts tucked, are the subtle things that separate the men from the boys.