1. A person purposely sporting clothing that looks so fashionable it's verging on silly.
2. A person wielding clothing or accessories that are designed to serve specific functions, in an ironic or trendy way.
See: Messenger bags, Fixed Gear bikes, glassless spectacles, Barbour jackets.
3. Persons so dedicated to acquiring the status of "an individual" they will follow the current hipster trends without question or hesitation. They will wear the clothes Vice magazine says they should wear, drink in the bars their favorite blogs tell them to, and walk around Shoreditch with an air of smugness only attainable by those in the knowledge that they are the coolest they could possibly be.
Serious Silly Wearers can also be seen sporting ironic moustaches and silly haircuts to further distance themselves from mainstream cliche's.