The first and only other time that I have visited Milan was over 20 years ago. I was 19 or so, and a close friend and I decided to take the train into Centrale without a place to stay and without a plan, other than to get into some trouble.

We ultimately succeeded at this ambitious plan. But I clearly didn’t see enough of the city, and I left thinking that it was a bit of a grimy and sleepy place. I was disappointed. I thought it would be fashion everywhere, and it wasn’t for me. And this impression has lingered with me ever since.

Boy have I been missing out.

I have fallen in love with Milan on this very short trip. It really is a capital of fashion and design. This is not a city of meandering tourists looking for the Pantheon (okay, there’s still some of that); it is a big city of business and culture. And if I had to compare and contrast it to other cities, I would say this.

Its built form is not nearly as manicured and as fussy as Paris’. In fact, in some ways, it’s a bit like Toronto. Its overall urbanism is messier, and you have to scratch beneath the surface and sneak into some courtyards before you really uncover its true beauty. But once you do, it’s magical.

At the same time, its street fashion strikes me as being slightly fussier. There is an effortlessness in Paris that doesn’t seem as pronounced in Milan (though it is still there). Here, there’s a little more flash and a little more, “I’m sexy and stylish, and I would like you to be aware of that.”

But this is not to say that you won’t see men and women in suits and stilettos riding a bicycle. It still feels effortless. It still feels natural. And when you’re here, you can’t help but feel like you’re probably not stylish enough for this capital of fashion and design.

The first and only other time that I have visited Milan was over 20 years ago. I was 19 or so, and a close friend and I decided to take the train into Centrale without a place to stay and without a plan, other than to get into some trouble.

We ultimately succeeded at this ambitious plan. But I clearly didn’t see enough of the city, and I left thinking that it was a bit of a grimy and sleepy place. I was disappointed. I thought it would be fashion everywhere, and it wasn’t for me. And this impression has lingered with me ever since.

Boy have I been missing out.

I have fallen in love with Milan on this very short trip. It really is a capital of fashion and design. This is not a city of meandering tourists looking for the Pantheon (okay, there’s still some of that); it is a big city of business and culture. And if I had to compare and contrast it to other cities, I would say this.

Its built form is not nearly as manicured and as fussy as Paris’. In fact, in some ways, it’s a bit like Toronto. Its overall urbanism is messier, and you have to scratch beneath the surface and sneak into some courtyards before you really uncover its true beauty. But once you do, it’s magical.

At the same time, its street fashion strikes me as being slightly fussier. There is an effortlessness in Paris that doesn’t seem as pronounced in Milan (though it is still there). Here, there’s a little more flash and a little more, “I’m sexy and stylish, and I would like you to be aware of that.”

But this is not to say that you won’t see men and women in suits and stilettos riding a bicycle. It still feels effortless. It still feels natural. And when you’re here, you can’t help but feel like you’re probably not stylish enough for this capital of fashion and design.