61. Casual Tailoring

As the lines between streetwear and menswear continued to blur, one of the more popular trends to come about was merging the two by dressing down items like sportcoats and trousers. We began to see guys like Kanye West rock snapbacks with tuxedo jackets, and Theophilus London wear Jordans with a suit. Unlike the '90s, the tailoring on the gear was on-point. It didn't hang off the body and definitely wasn't baggy. Yasiin Bey is among the rappers that have mastered the style. This aesthetic was marketed to guys via brands like J. Crew and Club Monaco, and guys everywhere tried to walk that line between dressed-up and dressed-down ever since.