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Jalen Rose’s draft-day outfit is widely regarded as the WOAT, but this discussion has always felt inauthentic to me.
If I think about this outfit for too long, it usually sends me into an existential crisis about what style really is, and what it means to me.
Why do I love so many of the old ‘fits that have been the most criticized? Am I trying to be contrarian, am I a sucker for novelty or do I love drama? Maybe, like most truly bold fashion shifts, folks at the time just weren’t used to the fits some of these guys were throwing?
The answer to all of those questions is “Yes,” but I genuinely do think this suit aged well while remaining novel and interesting. The beauty of fashion is in its subjectivity, but a great fit is self-expressive, enduring and often a little risky.
Rose said he wore the bright red because he thought he was going to the Clippers, which only makes me appreciate the risk more.
He had been pushing the envelope since his time with the Fab Five in Michigan, and his love of fashion remained throughout his career and now as a member of the media.
Style is about confidence and telling a story. Yeah, maybe that’s why I love Rose and all of his looks. I’ll leave you with this Q&A from his interview with GQ in 2020:
“Scale of one to ten, how confident were you when you wore that suit?
“100! I’m from Detroit. You heard Biggie say, ‘Pink gators, my Detroit players.’ We don’t get dressed. We wear outfits, OK? Just so everybody knows, I had two suits. It wasn’t like these guys now that have budgets. I had cubic zirconias. I had fake diamonds. I had a red and white suit. The second suit that I had was lime green with green gators. That morning, I was going to decide which one I was going to wear.”
Rose wore the higher-drafting team’s colors with confidence because he thought he’d end up there. He has fully owned that story ever since.
