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I'm a short fat middle-aged gay man who doesn't now know to dress himself

I've just started a diet (down 5 pounds so far.) I hope to get down to a 34" waist, (starting from a 40 inch waist.) A 34 inch waist seems like reasonable goal and it would allow me to shop in most stores. I wear jeans and polo shirts with the occasional short sleeved dress shirt thrown in. Can anyone suggest what I should wear? My company is very business casual and I live in San Francisco whose citizens are renowned for they're lack of style.

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