Ok, so I have always had a love of horrible sweaters and terrible 'ironic' clothing, even as a child (before it was cool, right?), and even now as a soon to be 30 year old, I can't stop loving my 'awful sweater' collection, and am always the first to pull them out when the temperature drops, and the last to put them away when the snow melts.
That being said, when does the irony stop being ironic, and start being trendy? Pairing a beautiful tailored skirt or nice jeans with a knit sweater of wolves might be too far, but I'm close enough with some of my mashups ;)
It is only now that I embrace my love of ugly sweaters, as I lose whatever semblance of embarrassment I may have had wearing them in public