Will literally walked in the door and the trends started popping. While the neon colors, the sideways biking cap and the Jordans certainly caught people’s attention, today one might argue that the most covetable item are his 5-inch (OK, maybe 6-inch) nylon shorts that vintage Patagonia Baggies fiends go brazy over.

Everyone and their mother has been, or is currently on, the short shorts train because every brand and their parent company are putting them out with their own twist, from Prada to Uniqlo and there is no stop in sight, but Will’s rendition provides a textbook tutorial on how to rock them well without recourse.

Many melanined folks will tell you that they won’t be caught dead with their toes out in public, so Will’s sock-adorned sandals at the Playboy Mansion party was not a new sight for black folks in the least. It’s even less of a shock to see today as many luxury looks are styled with strapped sandals down… well, to the socks. From Travis Scott’s Visvim red carpet Christos to runway-ready designs for the Dior Men’s Fall/Winter 2020 show, this toe-tucking trend may keep your toes from feeling the soft sand, but it’ll keep those barking dogs quiet.

Well, I’d be lying if I said I saw this one coming. When Will introduced his neck wallet (AKA pouch necklace; AKA collar purse) on the fairly serious (and extremely topical) episode “Guess Who’s Coming to Marry?” in Season 2, it was probably overlooked and an afterthought compared to the discussion around interracial dating from a black perspective. Nevertheless, Will still managed to pull the look off with ease, something not everyone in the 21st century who’s bought into the trend can afford to say. You can find wallets and key rings that fit this vibe from brands like Maison Margiela, Hermès and Aimé Leon Dore.

I’ll be honest, most of Carlton’s looks were satirical in the sense that they were made to serve as an extreme juxtaposition to Will’s “urban” look. It was the only way that Middle America could decipher between the black guy and the “black-guy-who-seems-white” guy. However, Carlton’s toned down prep look had an essence of the popular Ivy Style-look that inspired black guys (not to be confused with “black-guy-who-seems-white” guy) to prep up their attire, tossing a sweater over the Ralph Lauren polo, or simply wrapping it around their shoulders, down to the penny loafers. It’s no coincidence that Kanye West was often compared to Carlton when he went through his polo phase.

Will was no stranger to big bold colorful outfits, but it was his affection for big, bold, colorful graphic T-shirts that captured the hearts of teenage kids outside of major metro areas across the country. Whether it was to pay homage to some of his favorite NBA players or to show love for artistic patterns, Will brought his A-game and helped jump kick a revolution for streetwear companies who thrived off of (loud, giant, highly graphic) T-shirt sales in the mid-’90s and early-2000s. Today, now you’re seeing some of the same exact shirts Will rocked are selling for hundreds of dollars today on the vintage market, which—thanks to a blend of nostalgia for shows like The Fresh Prince of Bel-Air. If you’re looking for something that’s just as bright and bold (but not necessarily something that was literally made in the ’90s), we recommend brands that are blending cool with off-kilter—including Online Ceramics and Brain Dead.

Yes, we know who Mars Blackmon is. Yes, we know about the Bones Brigade skating in Jordan Is. There are plenty of cultural icons who helped popularize Jordans, but there are few who brought it to the mainstream like Will Smith did on The Fresh Prince. From his sitcom debut in the OG black Jordan Vs to those final moments of the last episode standing in the living room alone in his OG "Columbia" XIs, and all of the memorable moments in between, Will’s love for Jordans is only outmatched by our love for seeing which ones he might pull out of the closet the next week. Jordan obviously agreed, as the Fresh Prince has been blessed with three Jordan V retros to honor Smith’s role in the shoe’s popularity over the years.