From the moment he uttered those famous words, “show me the money,” Cuba Gooding Jr. had already developed his personal style sporting tailored suits and ties on red carpets and bowties and vests on the streets. 

Now, 16 years later, the Oscar winner is sticking to his refined wardrobe and looking better than ever. 

He’s swapped his paisley vest of the ‘90s for grey tweed vests in 2012 and solid collared tops for plaids. His jeans from the early 2000’s tend to have a darker wash nowadays and often times he may opt for a scarf over the bowties he rocked in his 30’s.  

Only time will tell how Cuba’s fashion sense will continue to adapt but our best bet is that we shouldn’t expect anything outlandish—and we’re not mad at that! 

—Lyndsay Luff