Photo of Tupac in an actual Business suit

TheBigBopper

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It was the 90s, to be fair and at least he swagged them shyts out and wasn’t looking like Frazier and Niles

season-2-pictured-david-hyde-pierce-as-dr-niles-crane-picture-id138361064
Jesus this shyt is horribly baggy, even for the 90s
 

karim

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It was the 90s, to be fair and at least he swagged them shyts out and wasn’t looking like Frazier and Niles

season-2-pictured-david-hyde-pierce-as-dr-niles-crane-picture-id138361064
This suit has a baggy cut, but it has a good fit (look at the shoulders and compare it to what pac wore) even though his pants could be shortened. Pac's suit was simply two sizes too big.
 

UpAndComing

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That's a cold Top 5, no order.

I'd still like to squeeze Jack Johnson and Malcolm in there, but where?


Man you got a point. Pre-muslim Malcolm and Jack were all the way swagged out. Both gotta be in the top 10

I'll even add Bobby Brown in the Dont be Cruel era
 
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