So here’s Simon Cowell at the casual Malibu Chili Cook-off wearing EXACTLY the same thing from head to toe that he wears on all his TV shows. A black or white t -shirt, those baggy boot-cut jeans, and pointy cowboy boots. The boots ($1000 a pair custom made by Berluti in Paris) have cuban heels and are built up inside to add three inches to his 5’7” height. So he can NEVER take them off without revealing his real height. The pants are deliberately long and wide to conceal his footwear. Simon is extremely wealthy – so why the unbearably monotonous wardrobe?
Photo Credit: BACKGRID-USA
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Can’t take him
He looks fine, he’s in good physical condition, and is dressed age appropriately. Don’t be such a hater about his height.
In answer to your question, he wears the outfit:
a. It’s his brand
b. It’s comfortable
c. Because he can!
Because being rich cannot compensate for having bad taste.