The 50 Most Stylish Fat Guys of All Time

8. Winston Churchill

Occupation: Prime Minister
Approximate Weight: 250+ lbs.

The British Bulldog had a wardrobe as serious as his love for alcohol. Even in the midst of wartime, he kept it fresh in an assortment of three-piece suits, pocket watches, bowler hats, and outerwear like double-breasted topcoats. He was every bit as dapper as a leader of his stature should have been, often photographed in a signature polka dot bow tie. If a heavier guy wants a style icon to model himself after, Churchill is a great one to aspire to.

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