How Pitti Uomo Insiders Mixing Tailored Pieces With Denim Shirts

Twice a year, the streets of Florence transform into a runway. At Pitti Uomo, the world’s most stylish men gather, and one unexpected garment keeps appearing under bespoke blazers: the humble denim shirt. Here’s how they do it.

Choose the Right Denim Shirt

This isn't the thick, rugged work shirt from a dusty Western. The key to this look is selecting a denim shirt that leans more towards smart than casual. Look for a finer, lighter-weight denim or chambray. The fabric should have a soft hand-feel, allowing it to drape elegantly under a jacket, not bunch up. The fit is crucial: it must be as sharp as a traditional dress shirt—slim through the body with high armholes. A spread or cutaway collar is ideal, as it frames the face and sits perfectly under a blazer’s lapels, with or without a tie. Washes should be clean and uniform, either a dark, inky indigo or a thoughtfully faded light blue. Avoid heavy distressing, rips, or overt western-style yokes and pearl snaps unless you're aiming for a highly specific, advanced look. Think of it as a dress shirt that just happens to be made of denim.

Master the Art of Contrast

The magic of this combination lies in the deliberate contrast between the formal and the informal. The texture of the denim plays against the smooth finish of a worsted wool suit or the soft nap of a flannel blazer. This high-low mix is what makes the outfit feel modern and unstuffy. For an entry-level approach, pair a dark denim shirt with a pair of tailored trousers in a complementary color like gray, olive, or beige. Add a softly constructed navy or brown sport coat. The denim acts as a visual anchor, grounding the tailored pieces and injecting a dose of American cool into a classic European silhouette. The goal is to look intentional, not like you grabbed the wrong shirt in the dark. The contrast should feel harmonious, not jarring.

The Full Suit Challenge

Wearing a denim shirt with a full suit is the expert-level move, but it’s surprisingly versatile when done right. This look excels with suits that are slightly more relaxed in their DNA. Think unstructured Neapolitan suits, soft-shouldered tweed, or casual cotton and linen blends. A crisp, dark business suit can be too formal a partner for even the most refined denim. A mid-blue denim shirt under a gray flannel suit, for example, is a confident statement for a creative workplace or a stylish weekend event. The denim instantly dials down the suit's formality, making it more approachable. The key is to ensure the rest of the outfit supports the decision. Leave the shirt's top button undone and skip the tie to maintain the relaxed vibe.

Accessorize with Intention

With such a strong statement piece at its core, the rest of your accessories should be chosen carefully. A tie is often unnecessary and can look fussy, but it’s not forbidden. If you do wear one, opt for a textural knit tie in a solid, muted color that complements both the denim and the jacket. It bridges the gap between the shirt's ruggedness and the jacket's refinement. Footwear is your next critical choice. Instead of polished black Oxfords, lean into the relaxed aesthetic with suede loafers, smart leather sneakers, or classic chukka boots. These options echo the casual nature of the denim shirt. A pocket square is a great finishing touch, but choose one that picks up a color from your jacket or trousers, not the denim, to avoid looking too matched.