How a Well-Dressed Man Completely Changed My Understanding of Style

Every morning he walked east as I walked west down one of Toronto’s busiest streets.

The first time I passed this Well-Dressed Man on my new route to work, he was dressed impeccably. Not that he was wearing a suit — he was more casual than “business casual” — but I could tell he did his hair, his clothes fit him well and he was wearing exactly what he wanted to be wearing.

He was easy to recognize when I passed him the next day; his hair coiffed the same way. Each time I saw him, he looked as put together as the day before. It wasn’t a uniform — although made up of a lot of the same pieces, he wore many different outfits.

As I noticed his style each morning, I was forced to notice mine. His consistent composure was like a mirror, reflecting back my own composure … or lack thereof.

I would feel smug and confident, an equal match, on the days I put together one of the outfits I felt my best in. It was as if I’d scored a point in a competition that only I was playing.

But then, inevitably, it would happen.

I would oversleep, lose track of time, have gone weeks without doing laundry and as I walked down the street I’d be aware, yet powerless to change how my appearance didn’t reflect the woman I was. As I bounced from impeccable to semi-peccable to what felt like a hot mess, Well-Dressed Man never changed. There was never a clear distinction between one of his “good days” and one of his “bad days.”

On a rainy morning, I pulled an old H&M jacket from the back of my closet (as it had a hood) and shoes that could get wet (since I already thought they were ugly.) Obviously, no one can dress well in the rain.

But there he was, as consistently styled as always, just below an open umbrella.

On another day I noticed a red nose and heard his cough. He was sick, yet he wasn’t wearing his “sick” clothes. I’ve always thought that when you’re sick, you must wear clothes that reinforce how you’re not at your best. You can’t possibly wear something you feel your best in. (That’s why I’d always worn leggings when I had a cold — even though they were only the slightest bit comfier than my Banana Republic trousers.)

Fall turned to winter and, as everyone knows, in winter you must pick between practical or fashionable. Even if I wore my favorite high-waist wide leg trousers or one of my winter dresses, I felt altogether disheveled when they were paired with a parka and boots.

However, in Toronto snow there he was. Same pant in a heavier weight with boots, a wool coat, hats, gloves and a scarf. Altogether looking his considered and put-together self. Just adapted.

As I bounced from impeccable to semi-peccable to what felt like a hot mess, Well-Dressed Man never changed.

No matter what was thrown at him, Well-Dressed Man was consistently his best.

As the owner of a style blog, I felt like a fraud — an imposter — as the disheveled outfits kept happening despite my ability to put together outfits I loved most of the time. Of course I had explanations: Style is easier for men. His mornings must not be as busy as mine. He must not be a daydreamer who loses track of time. But none of that was it.

After a full cycle of the seasons, I realized it was no wonder I couldn’t win this internal competition with him; I was playing a different game.

As I tried to dress better, I would try buying more expensive clothes, pieces that were more stylish than what I already had. Inspired by fashion bloggers, I shopped with the mindset of how a new piece was going to look on Instagram.

As I strived for style, his came effortlessly. Easy. He aimed only for consistency. It may seem like semantics, but these two objectives could not be more different.

Aiming for consistent style means you focus on what works best for you — instead of competing and trying to constantly one-up yourself. Aiming for consistent style means you know what is essential to who you are and communicate that — instead of trying to be all things and wearing all styles. And, more pragmatically, consistent style means you plan ahead for a style that is achievable instead of aspirational.

Aiming for consistent style means you focus on what works best for you — instead of competing.

Well-Dressed Man knew ahead of time how he would adapt his outfit if it was raining or snowing. Well-Dressed Man didn’t leave any bad outfits in his closet waiting to happen. His pieces were versatile and he knew precisely the many ways he could wear each one.

I no longer pass Well-Dressed Man every morning, but I see his effect on my wardrobe and my client’s wardrobes each day.

The Well-Dressed Man approach of consistent style was the missing counterintuitive piece of my style puzzle and has become an integral part of the style work I do with my clients. As long as we chase style, it will elude us. But as we focus on what makes us feel our best and put in the work ahead of time to make feeling good easy and achievable, then our best style and our best self becomes a reality.

No matter what is thrown at us.

What influences your personal sense of style?

Images via Molly Zaidman