When you go shopping for new clothes, there are probably a few basic questions running through your head, like, “How long will I actually wear this?” Or, “Do I have enough things to go with these?” Finally, “Will my parents disown me if I wear this in public?”

Nevertheless, there is one question that should probably be a little more common than it actually is: Can I wear this to work and out afterwards? The versatility of a piece isn’t always measured by the four-season fabric or its reversibility, detachability, or packability, but on just how many acceptable places and situations that piece can actually be worn. These following items really sum up what it takes to be multi-faceted and multi-situational, thus giving you the best return on your investment. (This is also a great term to throw out at your next business meeting). Don’t sacrifice your style for your work or casual attire when you can stunt on both with the best of them.

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