Men's Style Advice: Why Breaking the Rules Often Creates the Best Outfits

Some of my favourite outfits have never been planned. They happen almost by accident. You pull one piece from the wardrobe, then another, and before you know it you're standing in front of the mirror thinking, "That shouldn't work... but somehow it really does."

This was one of those outfits.

Everything I'm wearing is from Octobre Éditions, a brand I've always admired for producing timeless wardrobe staples rather than chasing trends. Individually, every piece feels understated. Together, they create something that feels far more interesting. And perhaps that's because it ignores quite a few of menswear's unwritten rules.

For years we've been told not to wear double denim. We've been told a tie belongs with tailoring. Jeans are casual. Shirts and ties are formal. Denim jackets belong with chinos. Smart shoes don't belong with relaxed denim.

Yet here we are…

A denim shirt sits underneath an ecru overshirt, paired with loose-fitting pleated jeans in a matching wash. Add a patterned tie into the mix and suddenly the whole outfit lands somewhere between classic tailoring and relaxed workwear.

It's difficult to categorise…

Which, I think, is exactly why it works.

The tie completely changes the conversation. Without it, this would simply be another elevated casual outfit. Add the tie, however, and it immediately introduces a touch of intention. It says you made a conscious decision rather than simply throwing clothes together. Ironically, that's exactly what happened.

The relaxed proportions also help soften everything. The overshirt isn't structured like a blazer. The jeans sit higher on the waist with generous pleats and a wider leg, giving the outfit movement rather than stiffness. Nothing feels forced. Nothing feels overly polished. That's the beauty of modern menswear.

We're moving away from dressing for strict occasions and more towards dressing around personality. A tie no longer needs a suit. Denim no longer needs to stay casual. Smart and casual no longer live in separate wardrobes.

Instead, they borrow from one another. Looking back at this outfit, I don't really see double denim. I see texture. I see proportion. I see contrast.

The cream overshirt lifts the blues. The patterned tie breaks up the denim. The relaxed silhouette keeps everything feeling effortless rather than corporate.

It's a reminder that style isn't about following rules. It's about understanding why the rules existed in the first place and then deciding whether they still apply. Sometimes they do. Sometimes they don't. And sometimes the outfits you remember most are the ones that were never meant to happen at all.