Monday morning in my favorite coffee shop. After greeting me warmly my favorite barista Jesse starts my americano, and then shouts over the din of the cafés morning rush “Your hair looks different. Did you dye it?”

STOP.

Here’s the most important thing I have learned about ‘beauty’ and the associated products, rituals, and criteria: no matter how elaborate, your look should appear effortless.

Beauty is timeless, ageless, and full of grace. Granted, some women never grasp this tenet and look like they applied their makeup with a trowel and learned their techniques from Cirque du Soleil.

Most men will learn sometime that even the most innocuous interactions with the fairer sex are booby-trapped. For example, the answer to the question “Does this make me look fat?” is always No. You should never honestly answer the question “What do you really think of my best-friend/sister/mother?” unless you still have your Plentyoffish account active. And you never, I mean never-ever, ask a woman about any sort of cosmetic modification.

“You’re not supposed to ask that, Jesse. It’s rude,” I sent back.
“Rude? You just dyed your hair. It’s not like you’re covering up grey or something.”

Sighhhh. This is why he’s my favorite barista.

If you read more of my posts you’ll learn that I am approaching a milestone: before the end of 2010 I will be thirty. It’s a number that haunts a lot of women—the end of a woman’s twenties means taking stock of what her twenties were. Rarely, if ever, is this a pleasant process, and in recounting my own twenties I do a lot of wincing.

The end of your twenties means your decade of laissez-faire beauty is over. It means you have to start watching what you eat, how much sun you get, how much water you drink, and what moisturizer you use. It also means, particularly for me, that you’re going to find a grey hair (or two, or two dozen.)

Grey hair is one of the most irksome beauty quandaries a girl can get into. It seems utterly impossible to hide or ignore them—even a single strand feels like a fright wig á la Bride of Frankenstein! And if you opt to dye your hair you’re committing yourself to an unrelenting cycle—every five or six weeks you’re back in the colourists’ chair or sneaking another box of dye out of Shoppers.

I’ve seen little greys popping up here and there for a few years. My first reaction was abject terror and I frantically pulled the hairs I hunted down with a hand mirror. I shudder to think how much time I spent in brutal self-reflection, despite my best efforts feeling defeated knowing there were miscreant strands that escaped my eye.

My high school was the proving-ground for individuality and I used my hair as a smoke signal, standing out from the crowd with a rotation of colours that ran the gamut from black to magenta. Mom was less than impressed that my graduating yearbook photo was adorned with fire-engine-red hair. Such a relief it was to finally return to my natural shade in the years following high school and university that I couldn’t bring myself to colour my hair out of necessity.

For the most part I’ve been able to ignore the multiplying grey hairs in my mane in the latter years of my twenties. I had to think beyond that whole age paradigm before coming to the conclusion that it’s what’s in my head, not what’s on my head that matters. How did I get past it?

Instead of looking in the mirror and scrutinizing myself to death, I looked at other women, beautiful women, women I admired. And you know what I found? The ones who appear the most confident, the most cultured, the most aware of themselves and their visual appeal while totally untouched by vanity are the ones who keep it really simple. Simple makeup, simple clothes, simple hair—executed with an elegance that makes their beauty indisputable.

Know why I like Dapper & Debonair? Because they use words like ‘authenticity’ and it’s not just window-dressing. What better way to show your style than to show your true self? That’s what it is to live the #dapperlifestyle—who better than you to play yourself in the story of your life?

From time to time you might want to switch things up a little bit—try out some suspenders, see what all fuss is about with leather apparel, maybe even change your hair colour. Experiment! The trick is that you’ve got to own it. Be honest with yourself about how you look and why, understand that no matter how you style yourself you’re always going to look like you, and appreciate all the great things you bring to the table before you start your morning routine. Only when you OWN it are you going to look amazingly, authentically YOU.