Damon Dash, Roselyn Sanchez and Cam'ron attend the spring opening of Sky Terrace at Ian Schrager's Hudson Hotel May 20, 2003, in New York City. (Stephen Chernin/Getty Images)

It's the early aughts in NYC. A young East African girl (by way of Canada) is preparing for her sophomore year of high school in the North Bronx. She had just spent the summer with her family in France, and just KNEW she was ready to be fresh to death with her back-to-school outfit.

At long last, the first day of school came around, and she stepped confidently off of her Bedford Park Boulevard stop, onto Jerome Avenue, and strolled on to campus…wearing yellow stretch camo pants, black ups*, a denim jacket, oversized hoops, and waist length straightback cornrows.

Now, I don’t know this poor soul, but rumor has it that she has since burned every single piece of evidence that this outfit ever existed - save for one photo that her mother is keeping in her photo album under close watch, presumably for blackmail reasons.

While this a truly harrowing tale, this completely random girl wasn’t alone in this tragic era of “urban fashion.” The late 90s and early 00s** were chock full of disastrous fashion choices. No one was safe from matching their laces with their belt, or wearing a blue and orange jersey dress because the Knicks are your favorite team.***

1. The Cropped Down Jacket


For when you’re cold, but your abs are on fleek. The entire Baby Phat Era was just a dark time for us all. God bless Kimora for keeping hope alive.

2. Name Jewelry


I had a friend who had a huge crush on a girl in high school, and wanted to let her know by buying her a gift for her birthday. He saved his coins and walked to the jeweler off of Mosholu Parkway to get her name on a chain with white gold plates. The week before her birthday he went to go pick it up… and the chain said “Keisha.”

Her name was “Keshia.” $200 down the drain.

I wonder if he ever ended up dating a girl named Keisha.

3. Ridiculously Baggy Clothing (especially on skinny men)


This one will never fail to befuddle me. I mean, baggy clothes were silly in general, but slender dudes were really out there in their older brother’s hand-me-downs just drowning in fabrics like that was the wave. While I think we’ve overcorrected in recent days with the skinny jeans - I am quite happy that “shorts that go down to your ankles” are no longer a thing.

I could go on forever - Avirex flight jackets, NBA jeans, kitten heels -  but I try not to insult the sartorial choices of folks who have done extended bids in maximum security prisons.

Please feel free to litter the comments section with your tragic outfit decisions - I know at least one of you guys was overcommitted to Coach accessories, or walked around with a toothbrush to prevent your white kicks from scuffing. This is a safe space!


Well, not really. But know that we will roast with love.

*Air Force Ones for the uninitiated

**Also, the present-day Bronx

***Whoever this poor girl is, I hope she has found some fashion sense. But she probably just thinks that crop tops are year-round attire.