Ms Ilaria Urbinati is one of the top men’s stylists in Hollywood right now. Some of the clients she’s dressed for the red carpet have included stylish A-listers such as Messrs Rami Malek, Chris Evans, Donald Glover and Ryan Reynolds. And now that it’s awards season, it is her busiest time of the year to be dressing up stars for the step and repeat.

But glamorous award shows and parties aside, the reality of full-time styling can be anything but – it takes a lot of planning, creativity and skill. And when compared to styling women, the knowledge and execution of a successful men’s red-carpet look is a whole different playing field. Below, Ms Urbinati offers an inside look at what goes into styling Hollywood’s best-dressed men.

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Where does your styling process begin?

The first thing I take into account is a client’s personality and personal style. Even someone who doesn’t have a good sense of style to begin with still has a certain look or feel to them, so I figure out what I think the best version of that is, and work to create a look for them that feels authentic. At the end of the day, good men’s style is whatever feels organic to that person. I figure out which brands to pull and make a list, then my assistant emails all of the brands. From there, I either pull options, in person or from photos. Sometimes I know exactly what I want them to wear going into it; sometimes I have a more general idea, then let the magic happen in the fitting.

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What signatures do you incorporate into all of your clients’ looks?

Colour is a big part of my signature as a stylist, so a lot of it starts from a colour story. When in doubt, I go classic and well-tailored. You can’t go wrong with that.

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How is styling men for the red carpet different from styling women?

Women love to try endless options, while men want to get through it as quickly as possible most of the time. For me, I find with men, the more assertive and decisive I am, the better. With women, you need to have a lot more back and forth. There’s just way more pressure on women.

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Who is a common male style icon that your male clients have referenced?

Ryan Gosling used to be a big one. Nowadays everyone’s feeling Brad Pitt in Once Upon A Time In Hollywood. But always classic guys such as Steve McQueen and Paul Newman. Personally, I really love Alain Delon, early Jack Nicholson, Ben Cobb, Helmut Berger, Richard Avedon, early Martin Scorsese movies, 1970s Robert Redford.

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What small details, that might be missed, are important when styling men?

It’s definitely all about the tailoring. But there are always small details that make an outfit work better, such as a good chain, a tank under an open shirt; certain kinds of bow ties or an air tie; the cuffs on a pair of trousers; opening an ankle to create a 1970s cut or tapering it in to make it more mod; quirky socks with a loafer. For me, menswear style exists in the details.

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What are some behind-the-scenes aspects of styling that may come as a surprise?

The amount of work that goes into it. The pre-production before a fitting, the days spent pulling the clothes and then the post-production of it. The tailoring, nailing down the details – whether it’s finding the perfect shoe for an outfit, or the right flower for a lapel. I’m pretty meticulous, so a lot of work goes into making an outfit feel new and unique. I just deeply love menswear and am constantly getting excited and obsessive about a new look or vibe to try out. There are no rules anymore. This can be a good thing or a bad thing. These days it can certainly go too far! But overall, it might be one of the most exciting times in men’s fashion.

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The men featured in this story are not associated with and do not endorse MR PORTER or the products shown