Performance Upgrade: Style

Hollywood's leading stylist gives us the 411 on dressing like a leading man

Hollywood Stylist Ilaria Urbinati

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Daniel Larusso had Mr. Miyagi. Neo had Morpheus. Luke Skywalker had Yoda.

Long story short, the value of a good mentor should never be underestimated — a truly savvy gent knows that the shortest path to improvement in any aspect of his life is via someone who knows the ropes better than he does.

And thus we bring you Performance Upgrade, a handy series in which we tap battle-hardened experts in various fields to help you elevate your game.

Today’s subject: the art of personal style, with ace Hollywood stylist Ilaria Urbinati.

Read on and dress well.

Our Expert

While you may not know Ilaria Urbinati by name, chances are you’re familiar with her work. Her client list reads like a murderer’s row of stylish Hollywood fellas: Ryan Reynolds, Donald Glover, Chris Evans, the Rock.

Long story short, this is the woman to whom men who need to look dapper but professional turn when they want to look their best. And if her tutelage is good enough for them, it’s damn sure good enough for the likes of us.

So your dutiful style editor journeyed to Ilaria’s private studio in the Hollywood Hills for an in-person styling session and a chat about how guys everywhere (not just the ones with their names on the posters) can up their sartorial acumen.

“The people with the best personal style are the ones who have a strong sense of self and who don’t take it too seriously,” she told us. “Style should be an expression and extension of self, it’s not about trying to be someone you’re not.” Duly noted.

Below, the rest of her tips on adding a bit of red carpet swagger to your daily routine:

Have a little fun with it — it’s just clothes. The second you overthink it, everything starts to feel off because it’s just too much anxious effort as opposed to a carefree, effortless feel.

On dressing for today’s more casual workplace:


“Build a work closet of items that are interchangeable. It helps to work within the same color family — so in other words, strong basics in neutrals that all work together. That way you don’t have to get up three hours early just to get dressed for work. Then add the occasional ‘special piece’ or pop of color to elevate an outfit — be it a cool shoe or jacket, a fun sock or a colorful sweater or belt.”

On the importance of precise tailoring:


“You’ll look slimmer and more fit in your clothes 100% of the time if they fit properly. I find most men who are either bigger or out of shape think the solution is to wear baggier clothes so as to hide, but actually it’s the opposite. Slimmer tailored clothes will lean you out. You can get away with a whole lot of rule-breaking and crazy prints or colors or whatever stylistically adventurous things you’re into trying if the clothes are perfectly tailored.”

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SHOP THE TIPS:

1. “Go with slim (not skinny, forget skinny) chinos over jeans. They look more professional.”

Fit 2 Classic Chino
Rag & Bone
$225

2. “I’m also a huge fan of taking dressy trousers and pairing them with a more casual top or jacket.”

Flowing Short-Sleeved Shirt
Sandro
$220

Checked Tailored Trousers
Reiss
$240

3. “A knit long-sleeved polo will be comfortable but look more professional and less like you’re on the golf course than a cotton short-sleeved one. And it’s handsome on almost any dude.”

Long Sleeve Fine Knit Polo Shirt
Paul Smith
$295

4. “A solid tee under a relaxed, unstructured soft-shouldered blazer also does the trick of comfortable but profesh.”

Slub Scallop Crew
Goodlife
$60

Navy Unstructured Linen and Cotton-Blend Blazer
Folk
$430

5. “For shoes, since the workplace is getting more casual, you can get away with a cool sneaker — that’s the one very youthful and casual piece that I would fully embrace.”

The Royale Blanco Gum
Greats
$179

On leading men to take your style cues from:


“Even though he’s not my client, I’d say the gold standard is Ryan Gosling. His style works for any guy, including fashion newbies. It’s very wearable but still adventurous and fun and outside the box without feeling like he’s trying to look interesting for the sake of looking interesting.”

“Also, my client Ryan Reynolds is a perfect example of someone whose style is very mature and put together but still looks youthful enough — never juvenile. He looks handsome and like a man. Never adolescent.”

“For really interesting and very fashion-forward style, my client Donald Glover is someone who has done a good job of doing something really cool and outside the box — really nothing too straightforward about his style — but who never ever looks like his clothes are wearing him or like he’s peacocking.”

SHOP THE TIPS:

1. “My favorite is the slightly more slouchy pleated trouser — if you find the right one, I think anyone (even smaller guys) can pull it off. The trick is to taper the bottom and not go too long on the length.”

Pierre Garment Dye Cotton Linen Pants
Officine Générale
$290

2. “I really love the silk shirt trend a la YSL (but tons of brands are doing them). More guys should embrace this. A lot don’t because it’s a little feminine perhaps … but there’s a fluidity to it that I find very sexy on a dude and it relaxes any suit or trouser.”

Shark Collar Silk Shirt
Saint Laurent
$990

1. They buy their clothes too big.
2. They don’t tailor their clothes.
3. The sleeves are always too long. I tailor the sleeve length on my clients on almost everything, NOT just suiting. Bombers, leather jackets, etc. all look better with a sleeve that isn’t bunching.

Ilaria, on style mistakes most guys make
Aggressive, but damned if it doesn’t work.

On easy ways to elevate an ensemble:


“Mixing prints! A no-brainer rule is to stick to no more than three different prints, and if you stay within the same color family (say, a few different prints but all in various shades of blue), you can get away with almost any print.”

“I LOVE a sweater under a suit, especially in a color, like a brown suit with a maroon sweater or a black suit with a baby blue sweater. Love it in the old preppy way over a white button-down, or just on its own. And this is the only time I prefer a V-neck over a crew — guys are always like, ‘I thought you hated V-necks!’ But that only applies to T-shirts, never to sweaters.”

A nice pop of color for a muted suit, no dress shirt required.
How’s this for “interesting?”

“Any time I see a guy with an interesting shoe or boot, I think it elevates the look.”

SHOP THE TIPS:

1. “I really love seasonal fabrics. I love a linen suit in the summer — embrace the wrinkles.”

Walton Suit
Billy Reid
$1295

2. “I live for a casual suede or leather jacket with no lining — it just feels and looks luxurious and light. It’s a very European look.”

Italian Suede Snap Front Dylan Jacket
Todd Snyder
$998

3. “Socks! Fun printed socks or bright solid colors. When you sit or walk and you see that pop it just makes people giddy.”

The Hemsley Ocean Mist
Ace & Everett
$28

Link Collection Orange
Thunders Love
$32

On accessorizing like a pro:


“Man jewelry! I love a good ring or two on a dude and a pendant on a chain. And mixing metals such as a silver chain with a gold pendant always looks great and unexpected. Please just stay far, far away from cuffs, leather, suede or beaded jewelry.”

“I also love it when a guy adds a cool unexpected belt. I’ve been known to say that I hate belts with suits (and I still stand by that), but there are so many exceptions. I just don’t like the ol’ office-looking black belt that looks like you’re just wearing it because your pants are too big and makes you look like an insurance agent. However, when I see a guy in a summery suit with a skinny little brown belt, or a colorful belt that makes an outfit pop? It looks awesome and like the dude really knows what he’s doing.”

I would say, if it feels cheap, it probably is. And if it’s cheap but doesn’t look it or feel it, then who cares?

Ilaria, on shopping wisely