9. Abercrombie & Fitch

I remember my first purchase at Abercrombie & Fitch. Yes, I bought a sweater vest. Shameful, I know. But what's more preppy than a sweater vest? And you know I wanted to be the preppy king of the world. Who wouldn't? Okay, don't answer that. I can even admit that I purchased the LFO CD (a purchase that becomes even more embarrassing now that I know that LFO stands for Lyte Funky Ones). But oh, how I loved that sweater vest. I wanted to wear it everywhere. I was certain, absolutely certain, that if the girls at my junior high saw me rocking such a classy piece of clothing that they would lurve me like no guy had been lurved before. Of course, I didn't account for my sweet bowl cut, and how it would severely limit any such lurving. And then to add insult to injury, Chandler Bing's trademark was a sweater vest. Just what I needed. I mean, look at what he's wearing. Being compared to that definitely can't be considered a compliment. He looks like a booger.