10. Dad Jeans
A cousin to sweat pants, shapeless, high-waisted jeans are the siren song of a man who has surrendered to a mid-life crisis. There is just no other explanation. Somehow, Obama pulls them off. As did Steve Jobs. But, chances are, you can’t. What you can do is turn back the sartorial clock by simply ditching the dumpy denim.
The Fix: Upgrade to snappier jeans (slim or straight-cut with a mid-rise) that sit at your waist. You can’t go wrong with an old school pair of Levis 501s.