5 Street-Style Ways To Redefine Cold-Weather Dressing

There’s a particular kind of surrender that happens every mid-November—the quiet, reluctant acceptance that the sun now clocks out before you do, and the wind has developed a personality of its own. Those linen skirts and open-toe sandals? Still glaring from the wardrobe, tauntingly optimistic. But the season’s shift isn’t just about layering up—it’s about redefining what warmth can look like.

Enter: the blazer. Once a symbol of corporate conformity, it has become winter’s most versatile companion—a bridge between structure and ease, style and survival. The street-style set has spoken, and their verdict is clear: this season, the blazer isn’t just outerwear. It’s attitude.

The Slouch Revolution

Vincenzo Grillo

This winter’s tailoring is less “boardroom boss,” more “borrowed from your artist ex.” Oversized and subtly deconstructed, the modern blazer drapes with intention, giving just enough shape to feel considered—but never constrained. Pair it with a pop-colour bag or bold accessories to remind winter that monochrome isn’t mandatory.

The Power of Shoulder and Shade

Vincenzo Grillo

For days when the cold feels existential, structure can be salvation. A sharp-shouldered blazer in a daring hue—think emerald, oxblood, or electric blue—cuts through the gloom like good news. Add oversized sunglasses (yes, even in November). Confidence isn’t seasonal.

Pinstripes, Reimagined

Vincenzo Grillo

Once shorthand for the corporate elite, pinstripes have found their playful alter ego. Lean into the full suit moment—slouchy boots, relaxed fit, and a knowing smirk. The aesthetic? Less Wall Street, more streetwise.

Ballet Flats, Revisited

Vincenzo Grillo

The early 2000s called—and for once, we’re happy to pick up. The ballet flat is back, impractical as ever, but charmingly so. When paired with a sweeping maxi dress and a tailored blazer, it transforms into something quietly rebellious. It’s the anti-commuter shoe—delicate, deliberate, and entirely unnecessary, which is precisely the point.

The Suede Story

Valentina Valdinoci

And then there’s suede: soft, poetic, and distinctly human. The suede blazer sits at the intersection of nostalgia and cool—equal parts Greenwich Village and effortless Parisian insouciance. For days when you crave warmth without weight, it’s the understated answer.

Daniel Usidamen

Author