Confidence Starts With How You Show Up with Stylist Ilaria Urbinati

Aug 25, 2026

Ilaria Urbinati, the celebrity stylist behind the looks of Ryan Reynolds, Chris Evans, and Dwayne Johnson, explores the powerful link between clothing and confidence. She discusses evolving your style without losing your identity, dressing muscular physiques, finding flattering colors and cuts, building an everyday wardrobe, and keeping fashion personal, playful, and authentic.

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INSIGHT

Clothes Can Create Confidence Before You Feel It

Confidence can come from clothing before it exists internally.
Ilaria describes clients returning transformed after seeing positive reactions in their first outfit.

ADVICE

Evolve Your Style Without Losing Yourself

Evolve someone beyond a rut without pushing them outside their identity.
Ilaria uses Donald Glover as an example of continually developing an already distinctive style.

ANECDOTE

Donald Glover Found A Calmer Style After COVID

Style must respond to fashion, personality, life changes, and body transformations.
After COVID, Donald Glover shifted from structured 1970s looks to looser, silkier clothing that matched his calmer identity.

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Renowned stylist Ilaria Urbinati, whose clients include Ryan Reynolds, Chris Evans, John Krasinski, Rami Malek, and Dwayne Johnson, joins Don to explore the psychology behind personal style, and why the way we present ourselves can have a much bigger impact on confidence than we realize.

Don and Ilaria talk about what separates people who feel comfortable in their own skin from those who don't, and how clothing can actually help build confidence when it's not already there. They discuss how personal style should evolve as we change, whether that's because of age, a new phase of life, a changing body, or simply a better understanding of who you are.

The conversation gets particularly practical for men: how to dress for your body type, why muscular physiques can change the way clothes fit, how to find the right colors and cuts, and why developing an everyday style is more important than simply having the perfect suit for a special occasion.

Ilaria also explains why the goal isn't to transform someone into a completely different person. It's about understanding who they already are and bringing out the best, most elevated version of themselves. And ultimately, she believes style should be fun, not something you take so seriously that you lose the effortless quality that makes it yours.

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