Go to an upscale retailer (Nordstrom, Neiman, Bloomingdales, etc) and get 2 pairs of nice jeans. They just plain fit better. I've also found that they're MUCH higher quality denim (ie, blended with lycra for better form/comfort balance). For casual, I have a few pairs of cords from J.Crew and most of my shirts are either Rugby or $15 tees that I find at random places. I'm also 30 and live in Connecticut so the same thing may not fly in other areas.
I wear a suit every day for work so I have my dress shirts custom made. I'm vaguely athletic but have a 17" neck which means most shirts that fit my neck are made for people that are 250-300lbs (read: YARDS of extra fabric). I got so tired of wearing parachute shirts that I had to go custom.
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