Think about where you are going first. Think about whom you might see -- especially if this is a business situation, or even a social situation where you might see a potential business contact. Dress appropriately for the occasion. If you're not sure what's best -- black tie or Juicy Couture sweats? -- ask somebody.
Grievous sartorial offenses I've observed multiple times:
- Real estate agents wearing jeans, yoga stretch pants, or raggy shorts while
showing a property.*
- Denim-clad women attending non-casual cocktail parties.
- Hoochie-mama attire in the workplace.
- Chest hair displayed in the workplace.
So what does your attire say about you? "Eff you"? or "I like myself"?
*This describes, sadly, about 99.9% of the real estate agents in Chicago. Who told these morons it's okay to look like you're picking up groceries, and you just happened to swing by to maybe make a buck? Show a little respect, lazy asses.