EMBRACE THE ITALIAN PRACTICE OF CLEANING YOUR CLOSET WHEN THE WEATHER CHANGES
"Since living in Italy, I do it. It's something so inherent in the culture that you don't even question it. It's not about space, it's about making the wardrobe accessible. I dry-clean everything apart from pants and socks. I'm also a big fan of chucking things out. Look at yourself in the mirror and make a judgment: 'Am I going to wear this in the next year? Yes or no?' If it's a no, it's time to get rid of it and make space for something new."

YOU'LL NEVER GO WRONG WITH A WHITE BUTTON-DOWN
"Since I've taken on the creative-director role, I've become a fan. It just frames you and makes you look more put-together than a T-shirt. Plus, coming from England, my skin is almost transparent, and I think the white gives my face a bit more color."

KEEP YOUR SUIT SIMPLE
"Go for a color that won't make you look like a bank clerk, and a performance fabric, like anti-crease. Choose a two-button, because a three-button goes in and out of fashion, depending on trends, and you'll get tired of a one-button."

WEAR A SWEATER UNDER YOUR SUIT JACKET
"Most people don't want to sit in a jacket all day, so the idea is to take it off and still have an undercover besides a shirt. Knitwear adds personality to the corporate uniform."

A GREAT SHOE IS A GAME-CHANGER
"Invest in one. Even if it costs three months in rent, it will change your life. It's what carries you—your motor. You can look undone in a T-shirt and jeans, but if you have that expensive shoe, you look done. I don't have a watch. I don't have jewelry. I have very little excess, but if I find a shoe I like, I'll buy three pairs. My favorite is a classic, heavy derby."

EASE OUT OF WINTER
"Change the outer piece. Get rid of the coat and introduce a lighter piece of outerwear, which makes it a little more fresh, and have a warmer layer underneath. Don't rely on the cover, rely on the layer."

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Surridge's Guide to Undiscovered Milan
Even though Milan is one of the world's fashion and design capitals, visitors often complain about the city's gloomy climate and industrial aesthetics. But look behind closed doors and there are treasures to be found. Here, the designer's top spots.

1. Villa Necchi Campiglio
Immortalized in the 2010 film I Am Love, this 1930s modernist architectural masterpiece boasts a small café in an outbuilding by the pool.
casemuseomilano.it

2. Sorrisi e Baci
This trattoria in the Porta Venezia neighborhood specializes in wholesome Italian classics. Go on a Thursday, when the chef often revives generations-old dishes.

3. Ristorante da Oscar
This establishment's boisterous namesake has filled the place with Mussolini paraphernalia, but fortunately the delicious pasta he serves up transcends politics.
ristorantedaoscar.com

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Tastemaker: Billy Reid
Tastemakers: The Duo Behind Maison Kitsuné
Tastemaker: Lulu Gainsbourg