Man With Style: Bill Cain, Founder Of Hat Of Cain

“Everyone ages differently, but keeping stylish and relevant in fashion can help you beat the age clock."

Man With Style
Bill Cain (Photo: Courtesy)
Bill Cain (Photo: Courtesy)

Bill Cain (Photo: Courtesy)

There’s just something about hats that give you that extra bit of panache and if Bill Cain, the 62-year-old hat enthusiast and founder of headwear business Hat of Cain, is to be believed, everyone can look good in one. The key, he says, is to find the right fit and style, and wear it with confidence. His hat soulmate? The Panama, a chic straw topper that adds a breezy, dapper touch to just about every look.

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Dandy Dressing In The Tropics

Cardigan, $1,900. (Photo: Brunello Cucinelli)
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“Opt for lightweight fabrics such as cotton and linen. Kimono jackets, cardigans and linen jackets are great layering staples for our climate.”

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Go-T0 Clothing And Shoes

Loafer, about $218, Berwick 1707 (Photo: YOOX)
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“I like our in-house linen shirts and Levi’s bottoms—they’re a great fit for me. Berwick 1707’s loafers as well.”

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The Hat Of Cain Customer Is...

Bill Cain fitting a hat on a customer. (Photo: Bill Cain)
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“... One who appreciates the art and craftsmanship of a Panama hat, and dares to stand out with an accessory that defines his or her style.”

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On Ageing And Style

Cain looking fly while cycling in sharp tailoring and a Panama hat. (Photo: Bill Cain)
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“Everyone ages differently, but keeping stylish and relevant in fashion can help you beat the age clock. My advice is to dress your age and have a handful of well-designed staples—they don’t have to be expensive.”

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Style Inspiration

Model Bernard Fouquet in a Brooks Brothers campaign. (Photo: 123RF)
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“I aspire to Bernard Fouquet’s relaxed look... the silver cuffs, the tattoos, the beard.”




Earliest Memory Of Fashion

A 1970s-inspired look from Gucci’s Epilogue collection (Photo: Gucci)
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“It dates back to the 1970s; I was in my teens then and had totally embraced mod-style fashion. I thought large-collared shirts, belts with big buckles and bell-bottoms were cool!”




Bag Essentials

Meisterstück LeGrand Gold-coated ballpoint pen, S$625. (Photo: Montblanc)
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“I must have with me my keys, sunglasses, Montblanc pen, laptop and mouse.”




Guilty Pleasures

123RF
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“Good whisky and cigars are definite weaknesses of mine.”




When Art Mirrors Life

123RF
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The Shawshank Redemption resonates because of the moral of the story everything is possible if you believe and work for it. It reminds me of when I first arrived in Asia and was determined to make this my home.”




Favourite Place

An aerial view of Positano on the Amalfi Coast in Italy. (Photo: 123RF)
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“Anywhere in Italy, because the weather is fantastic, the people dress well, and there’s great food and wine everywhere.”







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