Dressing for Fame: Ilaria Urbinati Talks Styling Shailene Woodley and a Gaggle of Hollywood’s Leading Gents

If celebrity status is conferred in red-carpet appearances, then no actress today can compete without the help of just the right stylist. As Kerry Washington once told Glamour after she noticeably upped the sartorial ante, “There were a couple of actresses whom I felt were having the upper hand careerwise—because they knew how to work that red carpet.” A carefully crafted collaboration between stylist and client, the perfect look can create an indelible impact on agents, casting directors, and those of us watching from the sidelines. Straight from the epicenter of all things celebrity, we’ve asked some of the industry’s top stylists to share their experiences and impressions from their perch above Tinseltown. With our Dressing for Fame series, we bring you an exclusive, insider look at everything it takes to create those iconic moments captured by a million photo flashes.

Ilaria Urbinati

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Sure, the ladies generally reign supreme on the red carpet, but sometimes it’s tailored menswear that gets our undivided attention. Stylist Ilaria Urbinati has A-list actresses (like Shailene Woodley) and dapper leading gents (including Bradley Cooper) on her client roster. The latter bunch call on her for every camera-captured turn. Here, she talks about styling politics, what it takes to prep a man for the red carpet, and why she thinks being a Virgo has helped her career.

—Alexis Brunswick

How did you begin styling?

I started out in retail. I was a buyer for various boutiques—Satine, Milk, and my aunt’s store Laura Urbinati—almost right out of high school. I would style a lot of the lookbooks and runway shows for the designers we carried in the stores. I eventually went freelance and just kept going from there!

What about your early experience sets you apart from other stylists?

I grew up in a family of crazy workers. Work ethic ranked really high in our household, so I’m a bit of a machine when it comes to the hours I’m willing to put in. I also grew up in Europe in a pretty artistic family—my mom and grandpa are art dealers, my father is a photographer, and my aunt and sister are both designers. I knew who Irving Penn and Richard Avedon were before I knew basic math, so this stuff’s been seeping in since before I even realized it. Having that mental database of fashion and the arts definitely affects my sense of aesthetic. I’m also a super anal-retentive and over-organized crazy Virgo, which makes me really efficient. I don’t know how in the world someone could be a stylist and not be super-organized—it would be impossible.

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You style a host of A-list actors, from Bradley Cooper and Chris Evans to Armie Hammer and Will Arnett. How does dressing men differ from styling women?

People always assume dressing men is easier. That’s true in the sense that there are way less politics than there are with women—there’s no fighting to get your hands on certain dresses that can only be worn once. But it isn’t easier in the sense that menswear takes precision and a certain meticulousness. It’s all about the details, tailoring, color combos, and fabric. Quality is key, and you can’t get away with a cheap suit. It’s really about trying to think outside the box because you have more limitations with menswear. I have zero interest in putting a guy in just another gray or black suit. But I also don’t believe in too many bells and whistles. You need to strike the right balance.

When dressing men, what’s the first step? Is it a collaborative process? And where do you find inspiration?

I’m always into some new thing, whether it be printed shirts or a new color combo, so I get really excited to try it on my guys. It’s always a collaborative process. It’s important to me that the guy always feels like himself, while maybe trying something new every once in a while. There’s a lot of camaraderie in fittings, so we make jokes like, “Shut up, look pretty, do what I say, and you’ll be the best-dressed you in the room.” I find that men are able to have such a great sense of humor about fittings and fashion—they don’t take it too seriously, in a good way.

Shailene Woodley has drawn a ton of attention lately for her head-turning red-carpet appearances. What is it like to work with her?

Shailene is just such a special human, she really is so heaven. We are always on the same page, and I think she likes that I don’t try to make her look like someone she’s not, but also encourage her to try new things. For instance, we do a lot of bright colors, which was new for her.

What’s the hardest part of your job?

The politics, for sure. You just want to do your job and put your clients in your favorite looks, but it’s not always that simple. There’s the celebrity’s team to contend with, there’s the designers’ wishes to keep in mind—like sometimes we’ll run into a problem when I want to put a dress on someone but the event won’t have photos. Certain designers only lend to certain girls but not others, and there’s not always any rhyme or reason to it. It’s all about who the designers like personally, basically—who they’re fans of.

Sometimes I feel like I have to play publicist. I’ll pitch the client to the designer: “Look how many covers they are on! Look at this big movie they have coming out! They’re blowing up!” It’s silly, but it helps!

What’s your favorite part of the job?

The relationship with the client. I feel lucky because I truly love my clients—some of them feel like family. It’s a really intimate relationship, to dress someone. And I love that collaborative process. The best compliment I can get is that my client feels like him or herself. And I would never want my clients to all dress the same. I don’t want them to have an “Ilaria signature look.” I want their look to feel unique to them.

I also love that there’s a real bond within this generation of stylists. We aren’t competitive and we root for each other. Kemal & Karla, Jeanne Yang, Wendi and Nicole Ferreira, Cher Coulter, Sam McMillen, Joseph Cassell—we are all buddies, and we are genuinely excited for each other when we have a great fashion hit.”

Fashion's most prestigious pets

The fashion industry's fondness for pets has been well documented – after all, no filter can improve one's Instagram feed like a fluffy creature – but there's a new pack leader in town: Cara Delevingne's rabbit and social media star, Cecil.

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Though it's nothing new for animals to become famous in their own right, as minions set up accounts for those without opposable thumbs, Delevingne's bunny has gone stellar. Although Cecil only joined Instagram on 14 May, the rabbit had 71,900 followers at time of press. This eclipses the achievements of fashion's previous most infamous pet, Choupette. Karl Lagerfeld's Dr Evil-worthy white cat may have her own maid, but she also has just 13,057 followers, despite joining Instagram in June 2012.

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Whether nestling into Chanel boxes or meeting Rita Ora, Cecil's life looks very pleasant indeed, although the bunny did have a near-death experience last week: getting trapped in a hole in the floor of Mulberry's headquarters. Thankfully, Cecil lived to hop another day, and he can now be proclaimed alpha fashion pet. Other significant players include super-stylist Katie Grand's lop-eared rabbit, Clara, as well as Brix Smith-Start's cheeky pugs. American Vogue's Grace Coddington is all about her collection of kitties – particularly calico Persian Pumpkin, the star of Coddington's own recently launched Instagram account, who, we kid you not, had a Balenciaga collaboration made in his honour.

Dogs – once seen as loud and unrefined, threatening to moult all over their owners' couture – now have baskets in some of fashion's most glamorous homes. Marc Jacobs' dog Neville is something of a pioneer – he's been photographed with "daddy" for a few years, and boasts a Love photoshoot on his CV. Kate Moss has Archie, a Staffordshire cross who looks great when combined with the wellies and Barbours of her Cotswolds lifestyle. Audrey, Donatella Versace's terrier, is anything but a country mouse. She's urban and has the wardrobe – including a gold and leather harness – to match. Like all of fashion's most adorable animals, Audrey is firmly on brand.

Seven Ukrainian Fashion Designers to Know Now

The first hints of the new wave of patriotism struck Ukrainian designers over a year ago, when Ksenia Schnaider used Trident, a national emblem of Ukraine, as a motif on her sweatshirts. Then the Kiev Fashion Days campaign featured Ukrainian top model Alla Kostromichova wearing a cape made of the yellow and blue national flag in March 2013, and designer Anton Belinsky used a huge flag to adorn the backdrop of his runway, dedicating his collection to the same colors—a sunny yellow and a deep blue. A month after his show, the revolution in Ukraine began.

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How did the fashion community react? Many designers were at Maidan Square, protesting by night, working by day, creating fashion stories on the streets of revolutionary Kiev and declaring their desire to live in a European country. When things started to heat up in early February, the majority of the country’s designers were preparing for their showcases in Europe—the Kiev Fashion Days show in London, the Fashion Scout showroom in Paris. Anna October and Julie Paskal, who were shortlisted for the LVMH prize, were trying to finish their collections on time despite the fact that their seamstresses were afraid to go outside.

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Leaving those scary times behind, designers from Ukraine are ready for the new future of their country—and continue to respond in full, creative force. “Fashion can also be a weapon of hope,” wrote Vanessa Friedman in a Financial Times article about a recent showcase of six young Ukrainian designers in Paris, and she was right: For the majority of the designers who represent the new generation of independent Ukraine, their work is their means of survival. No matter what the news headlines are, they continue to work and promote national identity, an issue that never had more urgency than it does now. Here, seven designers who are shaping the face of Ukrainian fashion now.

Lauren Laverne on style: contemporary fashion

Last week, in the spirit of indiscriminate friendliness – the practice of which is as close as I get to religion – I invited the internet out dancing. Predictably, among the cheerful chat my Twitter request provoked there was an obligatory dash of inexplicable, incandescent fury. I try not to mind these messages, preferring to think of them as energy flashes – the web runs on high emotions (love, hate, lust, LOLZ, mawkish sentimentality…) – and the occasional fuel spill is inevitable. Someone shouting YR DOGSHIT LAVERN in response to a benign status update on social media is the equivalent of your hairdryer blowing a fuse.

Anyway, I was told to act my age. Which struck me as interesting, because I was. I'm 36. In 2014 that makes me a retired young person or an apprentice middle-aged person, maybe both. I'm part of the hipster diaspora, created by a consumer culture that doesn't want me to stop wanting things.

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The conflicted nature of my chronological position was precisely what made the idea of asking everyone within earshot to come dancing droll enough to post. Clearly I was implying that I was young enough to want to go out and tear up a dancefloor but too old to bother to do much about it with anything other than my thumb. As we all know, the moment your house becomes nicer than a nightclub is the tipping point between youth and adulthood. For me, that happened long ago.

I mention this because while nightclubs are still for the officially young, fashion is getting better at catering for those of us who are sitting astride the ungovernable pushmepullyou of middle youth, unsure which way to go. The new watchword to look out for is "contemporary". A longstanding fashion adjective in the United States, contemporary fashion is a nascent – but potentially lucrative – category in the British market. It sits above the high street price point and at the low end of the designer one. It isn't midmarket. The difference between contemporary fashion and midmarket fashion is, well… fashion.

The pursuit of new trends (tempered by a certain amount of age-appropriate sophistication) trumps the idea of "classic" style. These are clothes for those of us who no longer live in the land of the young but for whom it is still home.

Whistles is the first British brand to market itself as contemporary, and the popularity of imports such as J Crew and Michael Kors has been growing apace (while Net-a-Porter stocking Kate Moss's sellout range for Topshop suggests the boundaries between high street and high end may blur further). What it means for your wardrobe is that covetable clothes you can actually wear will be available as long as you keep shopping. That's the trick – whether it's being played on you or by you is a question of perspective.

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Claudia Winkleman's fringe politics

It was once voted the most annoying of its kind on TV and even has its own Twitter account (though, really, which celebrity body part doesn't these days?). It is, of course, Claudia Winkleman's fringe. Once long and sweeping, tickling her eyeliner and giving the presenter a coquettish charm (or irritating skittishness, depending on your view), said fringe has undergone a remarkable makeover, according to an article in the Daily Mail. It has been trimmed.

Those wondering whether losing less than half an inch of hair merits an article, or indeed a blog about an article, are clearly strangers to the intense, lengthy and repetitious discussion that often accompanies a woman's decision to have a fringe. And once she has exercised her right to choose, said discussion continues as the fringe grows. "I was thinking about growing it out," they'll offer up to uninterested co-workers, "but now I'm wondering whether to have it shorter."

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In Winkleman's case there might be darker forces at work, and those forces work at the BBC. The 42-year-old presenter will replace Bruce Forsyth to front Strictly Come Dancing later this year (or, according to Forsyth, Winkleman will replace Tess Daly, who will in turn replace him). Perhaps, noting that Forsyth has never succumbed to the allure of a fringe, Winkleman is apparently reconsidering her look. "It is probably no coincidence that she went for the chop just in time for her new job … as she once admitted BBC bosses think her fringe is 'ridiculous'," claimed the Daily Mail. And if there's one thing Strictly fashion is not, it's ridiculous.

But it's not just BBC bosses who are preoccupied with fringes. Michelle Obama's "bangs" lasted less than a year before the first lady grew them out, learning what many women will at some point in their life. "It's hard to make speeches with hair in your face," she said. The Guardian's beauty columnist Sali Hughes described getting her fringe cut as "thoroughly cheering", while TV editor Vicky Frost was told to get her fringe out of her eyes by one reader (and in the interest of veracity, it should be noted the author's byline picture is old and her fringe is long gone). In an episode of BBC3's Him & Her, a large part of the plot hovered around the merits and perils of a fringe wash – soaping your fringe under a tap while leaving the rest of your hair dry. One can imagine this lack of tonsorial decorum, so at home on BBC3, doesn't quite cut it on primetime BBC1. Not on a Saturday night. Not on Strictly. But be warned. Winkleman's fringe trim is just the start of it. They'll be after her eyeliner next.

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Thinking of buying dungarees? Just don't expect them to transform you into Alexa Chung

OK, before we deal with your Dungaree Problem, Charlotte, we need to talk about your Compliment Problem. Let us dissect this telling sentence: "My girlfriends say I look good in them, but I don't really believe them." There are three possible readings of this sentence. First, that it is what is succinctly known as a Humblebrag, in other words, a comment that sounds like self-deprecation but is actually just a way to brag, such as: "OMG, I am such a heifer I can hardly fit into this new dress my boyfriend Ryan Gosling bought for me." But I reckon we can dismiss this option because you don't strike me as a humblebragger, Charlotte. You strike me as a confused person, which brings us to option two. Namely, you don't trust your friends when they say you look nice specifically because they are your friends.

I sort of understand this thinking – your friends wouldn't want to say anything that might hurt you, because they are your friends – but only to an extent. What is the point in being friends with these people if you don't trust them? To say that you can't trust those closest to you to tell you the honest truth is a mere half breath away from believing the mean comments of strangers online, and that, Charlotte, will get you in a right muddle. Believe your friends. They love you enough to come shopping for dungarees with you, for heavens' sake, and you chose them as friends because you, hopefully, respect them. Trust your friends.

The third and possibly more plausible possibility is that you don't believe compliments from anyone. Here, again, our path to comprehension bifurcates and we have two options in front of us: you say you don't believe compliments because you think to do otherwise would be unspeakably arrogant, or you genuinely do not believe compliments. These two issues are not necessarily mutually exclusive but taking the former option first, this is an all-too-common belief among British folk in my experience, far more so than among my fellow Americans. Which is not to say that Americans don't suffer from it, particularly the women, because, unbelievably, too many women are still conditioned to think that accepting a compliment is unfeminine. The American comedian Amy Schumer satirised this brilliantly on her Comedy Central show, where a bunch of women stand around rejecting each other's compliments in the grossest of terms ("Look at your little dress!" "I look like a whore locked out of her apartment") until one of them finally accepts a compliment and the rest of them immediately self-implode in horror. Ladies, stop being so masochistic (and rude): accept the compliment.

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Or there is the final option, which is that you don't believe any compliments from anyone, ever, because your self-esteem is that low. For this, seek professional help, because you are being horrible to yourself.

And we now, at last, get to the dungarees. Are they a "sensible" purchase? Of course not, as you well know. Dungarees are not something you're going to wear every day (and, to be honest, I'd wager that at least one quarter of the people who buy dungarees this summer will wear them precisely once before dumping them at the local charity shop). Dungarees, as the very wise and funny comedian Nat Luurtsema once wisely and funnily said, "are like a fancy hat, in that it's obvious you had a thoughtful moment that morning before you went, 'Yeah. I am wearing this'." There is no justification for wearing dungarees – just as there's no justification for wearing what I call a Statement Hat, ie a hat that has no practical purpose. You are only wearing said hat or dungarees for your own enjoyment and to make something of a statement to others, that statement being "I'm the kind of person who wears dungarees or statement hats."

All you need to decide, Charlotte, is why you want to buy these dungarees. Let me tell you a dungaree-ish story. A few years ago, a woman who we'll call Yeldah saw a picture of Alexa Chung in a magazine wearing what I guess is called a dungaree dress. Chung looked great in her dress, sort of like a modern version of 1970s Linda McCartney, and so Yeldah – despite being a sentient adult person who is allowed access to motor vehicles – thought: "Yes! If I buy a dungaree dress I will look exactly the same as Alexa Chung, even though I am not actually Alexa Chung and have a totally different body type!" Reader, Yeldah was me and I did not look like Alexa Chung in my hastily purchased dungaree dress. I didn't even look like Linda McCartney – I looked like an idiot whose body type (narrow of shoulders, broad of beam) is totally wrong for this dress. And lo, Oxfam soon found itself blessed with a once-worn dungaree dress.

What I'm saying, Charlotte, is I know that dungarees are trendy at the moment and, by all means, give them a go. But don't buy them because you think they'll magically turn you into whatever celebrity was photographed wearing them this week. The only reason to get them is if you actually like the dungarees themselves, and feel comfortable in them. And for the love of Mary, learn to accept a compliment, yeah?

Advanced Style: a much more joyous way of ageing

There are some occasions in life that are rather hard to dress for. Take Tuesday night and the European premiere of Ari Seth Cohen's Advanced Style documentary. I hosted a Q&A before the screening, and I changed my mind three times in the space of an afternoon before reverting to my customary black. Twitter advised "mad shoes", so I wore the last great folly of 2013 – the pair of red suede Prada heels I bought for my father's funeral. Those shoes mean business, and wearing them felt a little as though the Aged Parent was there, holding my hand (or my feet). Still, you can see my difficulty given the abundant style promised by the evening.

The great gift of Cohen's film, funded largely by Kickstarter, and directed by Lina Plioplyte is that you gain an insight into a much more joyous way of ageing. An intimate illustration of how six uniquely stylish women live their lives, it's not all pretty hats and fripperies, nor is it a propaganda flick for the senior citizen. It is a celebration of life at its later stage. From my perspective, it was interesting to watch the audience watching the film and to hear the laughter when Ilona Royce Smithkin (93) quips that she no longer buys green bananas; or when Zelda Kaplan admits she no longer dances as much as she would like to because most of her partners are dead. There was a hoot of relief that someone mentioned death and wasn't immediately walloped with a biblical smiting. Alas, for Kaplan, 95, that came later, during New York fashion week 2012, although as Tziporah points out, she went doing something that she loved, and wouldn't we all want to do that?

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I've seen the film six times now and could happily watch it six more because it truly is that much-abused term life-affirming. It's true there is a similarity with last year's homegrown Fabulous Fashionistas in that both films profile older women creating a fashionable life beyond what society maps out for them, but the New York senior way of life is beautifully observed here. Cohen told me that he found Londoners much less receptive to being style-snapped in the street - why aren't we having as much fun as our Big Apple sisters? Of the women who appear in Cohen's film and who sat alongside me on stage on Tuesday night, there was only one in black (apart from yours truly) – Joyce Carpati who uses it as a background for long strings of pearls and colourful wraps. With her thick silvery plait (last night studded with tiny gold flowers), black snood and luminous skin she was astonishingly elegant. Tziporah Salamon was wearing a lot of black, but had iced it with scarlet. From the platform shoes – "see, they're made like an ice-cream sandwich!" – to the razor-sharp bob and beautiful lacquered button hat topped with crimson peonies and long scarlet tassels, she was a walking work of art. Debra Rapoport, makes, or should that be "sculpts" her own hats and many of her clothes herself, but much is sourced from "thrifting". Lynn Dell, the self-described "countess of glamour", was dressed from head to toe in beautiful azure blue silk complemented with the biggest costume pearls I've ever seen.

What each of these women has in common is that they insist that style has nothing to do with money – "fashion says 'me too', style says 'only me'" says Dell – this is about creativity and looking good to feel good. As Iris Apfel says, "everything I've got two of, one hurts". We all need something to soothe the frazzled spirit. Jacquie "Tajah" Murdock (82), elegant in powder-blue vintage Courrèges, is almost blind with glaucoma but didn't let it to stop her being photographed for Lanvin and nor will it stop her dancing at a charity benefit later this week in New York. I think we can all take a lesson from that. Go and see the film and be educated.

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Met ball turns to high society, but can the high street cash in?

It is widely judged to be the fashion world's most extravagant night out, wielding huge influence over trends on the high street. This year's red carpet will be graced by a host of celebrities including Lupita Nyong'o, Sarah Jessica Parker, Taylor Swift and Kim Kardashian as well as industry VIPs and some of the wealthiest people in the world, each splashing out $25,000 (£15,000) on a ticket.

The influence of the New York Metropolitan Museum of Art's annual gala opening for its annual fashion exhibition has spread far beyond upper echelons of the industry as fashion retailers watch for a new trend that they can cash in on.

"It's probably the most looked at event in the fashion calender, even more so than the Oscars," says Gemma Hayward, senior fashion editor at Grazia magazine.

Last year's exhibition, Punk: Chaos to Couture, which examined the influence of punk on high fashion since the early 1970s, led to retailers, including Zara and asos, doing a roaring trade in studded sandals, while the Superheroes theme of 2008 meant that cartoon-printed superhero T-shirts littered the high street.

More recent, playful themes have been interpreted by celebrities looking to score red carpet publicity points – with mixed success. Beyoncé's take on punk in 2013 suffered charges of resembling a dictator's interior decor, and worse, of being unflattering.

However, the focus of this year's exhibition "Charles James: Beyond Fashion" – a retrospective of the 20th-century British-born, American-based couturier – may pose a problem for high-street brands looking to turn the look of the Met ball into sales. Guests are expected to embrace the high society theme with extravagant ballgowns and elbow-length gloves likely to take top billing. It is a look which, unlike last year's punk theme isn't so easy to reinterpret on the high street.

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"It is in direct contrast to the last Met ball," said Hayward. "More rarefied and historical. That's more challenging and less likely to be absorbed into the mainstream."

Charles James was little known beyond a circle of industry admirers and wealthy couture clients. In the 1940s his contemporaries referred to him as a genius, with Christian Dior crediting him with inspiring his new look and describing his work as "poetry". Fellow designers, including Coco Chanel and Elsa Schiaparelli, wore his designs (the former wasn't required to pay for her dresses, but the latter was) while life-long friend Cecil Beaton photographed an elite set of fans wearing them. A perfectionist and defiant elitist, James reportedly once said that he felt there was not enough money in the world to buy his garments. But despite his eccentric personality and the many compelling details about his career the designer does not feature prominently in fashion's history books.

The exhibition will also be the first at the newly reopened Anna Wintour Costume Centre. The wing was previously known as the Costume Institute but was renamed in recognition of the US Vogue editor's huge fundraising efforts over the past 16 years. The theme suggests Wintour's agenda includes repositioning the event – and indeed her own fashion legacy – as worthy of a museum as opposed to quirkier themes of recent year that have subsequently appealed to fashion's playful side.

There have been some rumours from American media sources that Wintour – who will co-host the party with Sarah Jessica Parker and Bradley Cooper– "wants more exclusivity." A theory given weight considering that tickets are $10,000(£6,000) higher than last year's price, and that the theme focuses on a couturier who could never be described as egalitarian.

Vogue, one of Wintour's mouthpieces, has already suggested that the Charles James-themed Met gala will signal a return to "old world elegance on the red carpet". The white tie and decorations dress code – which has raised eyebrows for its deliberately rigid sartorial implications – will mean it says "many of the chicest attendees will be wearing custom cuissardes made by ancestral French glovemakers".

Commentators are in agreement that, although unlikely sounding, long gloves could be an unexpected commercial trend to reverberate down the fashion food chain as a result of the event. "The very strict dress code will be difficult for anyone watching to translate into their everyday wardrobe, but long gloves were all over the autumn/winter catwalks so they are probably the easiest part of it," says Hayward.

Kay Barron, fashion features director at Porter magazine agrees: "actually I'm quite feeling long gloves for next season, but rather than a specific trend piece, I think it will inspire a love of dressing up again. Gowns have been out of fashion for so long, even for black tie events and I think everyone could benefit from getting a bit fancy from time to time."