How to Dress Well: The Myth of Dressing Appropriately
(image: courtesy of Drake's London)
The thin line between situational dressing and wearing what makes others comfortable around you.
When was the last time you wondered: "Am I too old to wear this?" If it's recently, you're not alone. Questions like these seem to pop up more often after hitting certain milestones—like entering the big 3-0, 4-0, and beyond. Yes, age is just a number. But it often comes with unspoken expectations about what's "appropriate"—expectations that, when we dig deeper, are more about societal pressure than personal preference.
Why style still matters
How we are perceived comes down to our demeanor and… our clothing–let that not be a surprise. Blame our superficiality as a society or simply accept the fact that this is how it is, thanks to our ancestors. Out of survival instinct, judging someone's appearance was the only thing to help determine a possible threat.
The good news? In today's world, your style is a tool to connect with others, build trust, and project confidence. The key is to master something I call Situational Dressing—the art of knowing how to dress for any occasion while still staying true to yourself. Yes, classic dress codes help at formal events. But that's like 5% of life.
Your personal brand to set the tone
Since dress codes have gotten a more relaxed approach in the corporate world, you need to use your own imagination and creativity a lot more. And I'm not mad about it. Because that means you can explore the boundaries of your personal style with way more freedom without being declined at the entrance.
Within your personal style, though, it's key to match your outfit to the occasion. If not done well, this may limit your ability to close important deals as well as a second date. To excel in situational dressing, reading the room, and connecting with your clients, business associates, and people around you does 80% of the job already. The only things to keep in mind (hopefully redundant, but):
Dressing too formally in B2B meetings
Showing up in a suit and tie for a casual meeting with a young, creative agency can make you seem out of touch or rigid. On the flip side, dressing too casually could appear unprofessional. The sweet spot? A smart-casual look that says, I'm adaptable, capable, and confident.
Dressing too low-effort on a first date
It's nice to see you've put in effort. Not just because you're on a date with someone, but even more because apparently you care enough about yourself to do so, too. Taking the time to put in the effort to put together a look that's authentically you. This could mean tailoring those jeans to fit perfectly, wearing that new bracelet, or simply making sure your favorite shirt is clean and ironed.
Don't dress to shrink yourself
Here's the thin line.
Situational dressing doesn't mean dressing down to make others comfortable. It's not about minimizing yourself or dimming your light. That's the equivalent of making yourself appear less skilled in order to make other people feel like they are more and better than you. Wearing something bold might make someone else feel underdressed—but that's their issue, not yours. Dressing for the occasion doesn't mean sacrificing the things that make you feel confident and authentic.
Why? Because confidence is your best asset. It's what people remember long after they've forgotten what you wore. And confidence comes from knowing your style is an extension of who you are—not just a reflection of where you are.
The truth is that this skill takes practice—but once you master it, you'll never find yourself second-guessing a great outfit again. 😉
Personal branding, done for you.
If you've been wondering how to create that authentic style that reflects your personal brand, I'd love to help. My men's personal styling services are designed to help entrepreneurs like you feel confident, put-together, and effortlessly stylish—no matter the occasion. Book a free consultation to get started here.