The Fresh Prince's 25 Greatest Outfits

Image via Complex Original

25. Multi-colored Vest, Jeans, and Air Jordan VIIs 

Episode: 66 

Clothes getting weirder — as the show progressed Will still continued to push things with his fashion sense, donning crazier patterns and color mixtures including this multi-colored vest layered over an orange tee and paired with "Cardinal" Jordan VIIs. 

24. Red Vest With Black & White Pattern, Matching Hat, Black Jeans, Nike Air Sonic Flights 

Episode: 60 

Crazy patterns were a part of The Fresh Prince's Modus Operandi and the simplistic black and white designs quickly took over in the mid-90's. Were these custom joints or something straight from the store? We're not 100% sure but either way you know Will had to have a connect. 

23. Red Vest, White Graphic Tee, Snapback Hat, Black Jeans, and Air Jordan VIIs 

Episode: 62 

That Mo' Town Philly style was tough to beat — dressed up and casual at the same damn time. In season three Will started to mature the style a bit but still keep things laid back enough for a family BBQ at the Banks' crib. The Jordan VII "Hares" too, never disappoints with the small screen stunting. 

22. Purple and Lime Green Contrasting Shirts, Zubaz Pants, and Air Jordan Vs

Episode: 2 

The purple and lime green hit back-to-back episodes and it wasn't even the same outfit. The zebra-striped Zubaz pants had a cult like following and the Jordan Vs were just as important at the time too. How Will came up with the color combos and patterns is a mystery but he pulled it off. The biggest question might be how the hell did Jazz get that drum set upstairs without Judge Banks murking him. Oh yeah, this .gif too. 

21. Short Sleeve Henley, Jeans, and Air Jordan XIs 

Episode: 148

In the final episode Will says his goodbyes to the Banks family and to an era where he ruled television for half a decade. He moved onto bigger and better things and he left the show on a high note with a Henley, jeans, and one last final stunt rocking the All-Star Game tested "Columbia" Air Jordan XIs. 

20. Silk Shirt, Black Jeans, and Nike Huarache Runners

Episode: 42 

When you have that Bel-Air financial backing it's easy to diversify the closet. Silk shirts and black denim were the rage in 1992 and Will always had to stay laced in the illest sneakers our, Huarache Runners easily suffice. Most people might be more familiar with the Huarache Trainers but after Will let Philip Bank's arch-nemesis, Jazz, crash at the crib we are pretty sure he scooped a pair of runners to get away from Uncle Phil the easiest way possible — actually moving at a moderate pace. Always scheming Will, we see you.

19. Lugz Quarter-Zip Sweatshirt, Jeans, and Nike Air Max 95s 

Episode: 147 

Large branding wasn't cool until the show was almost a wrap. The quarter-zip red, white, and blue quarter-zip stayed true to Will's Philly ties. The Air Max 95 is usually ranks atop most runners best of lists. In the second-to-last episode, Will busts them out during a family meeting. The design on these were really a step up from a lot of the Nikes at the time with extra details. 

18. Silk Button-Up Shirt, Jeans, and Nike Air Force 180 Highs 

Episode: 30 

The silky-smooth shirt paired with denim and high-top white kicks was a must in the early-90's (90210 and Saved By The Bell anyone?). All that gear had to have been a few months allowance. When your Uncle Phil is getting that government money, a $100 for the shirt and jeans and $175 for the sneakers is nothing. 

17. Knit Sweater and Khakis

Episode: 105 

Everyone grows up at some point and when Will Smith started to become a man he started to dress like one. While contemplating marriage and starting his own regime the clothes match the maturity as The Fresh Prince trades in his oversized hats and multi-colored shirts for a tonal knit sweater and khakis — still fresh. 

16. Denim Button-Up Shirt, Jeans, and Nike Air Force High 

Episode: 95 

The two-toned denim on denim look is always dope if executed and Will killed it with one of his more conventional looks. No sneaker made as many appearances throughout The Fresh Prince of Bel-Air than the classic Nike Air Force High — it wasn't even close. They saw his first apartment (which he was kicked out of within 24 hours), Carlton losing his virginity, and Will meeting his biological father. 

15. Black & White Striped Rugby, Jeans, and Nike Air Up 

Episode: 116 

The Fresh Prince in simple colors and classic styles didn't get enough love Will rocks another — here is one of Smith's cleanest and bets looks yet. Rocking another Pippen exclusive in season five was just further proof that he was more than Jordans. 

14. Windbreaker Jacket, Skidz Pants, and Nike Quantum Force 

Episode: 6  

Was it the outfit? Will and Carlton have a run-in with the five-oh for a suspected stolen vehicle and Will's high-fade, windbreaker, Skidz, and Nikes probably didn't help in his defense. The Fresh Prince made the outfit a go-to move in the projects and the suburbs alike, loud colors and Nikes became a staple in everyone's closet. 

13. Starter 76ers Hoodie, Jeans, and Nike Air Maestro 

Episode: 99 

As Will takes the show back to Philly he reminisces about how his life might have been had he never left for Cali, while rocking his Starter 76ers hoodie — hardly home but always reppin'. The kicks didn't show any love to his Sixers squad — we see you rocking the "Pippen All-Star Reds" in what was supposed to be the final episode of the show. You may not know the show was cancelled after season four and syndicated — when reruns were hitting numbers almost as high as the originals they decided to add on a fifth and sixth season. 

12. Design Pocket Tee, Skidz Pants, and Air Jordan Vs

Episode: 5 

Denim was far from a fail in the 90's but Skidz and Zubaz were the shit. Why wouldn't you want to rock the most comfortable baggy pants that were basically glorified pajamas? In the first season Will paired them with a designer pocket tee shirt which blew up again in 2012 and a pair of "Grape" Jordan Vs set to re-release this spring. Dude really was ahead of his time — having a sick wardrobe budget couldn't have hurt. 

11. Blood Orange Denim Jacket and Matching Hat

Episode: 62 

The Fresh Prince was all about matching his hats and shirts (please don't try this now) and it turned out to be part of what defined his style. Through all the seasons there might not be a doper look than his blood orange denim jacket with the matching snapback. Okay, on second thought try this if you want, dudes are out in the streets wearing skirts. 

10. Flannel, Jeans, and Nike Air Maestros 

Episode: 87 

The best part about Will Smith's style was he had the courage to do things most people couldn't wear outside of a music video. He also killed it in toned-down outfits that every kid could appreciate. In episode 87 he paired up a flannel and jeans—nothing too wild or over the top, but definitely one of Will's best outfits on the show. Sometimes less is definitely more. 

9. Mafiaso Suit

Episode: 31 

Will makes an appearance on The Oprah Winfrey Show (seriously! the cameos on this show are craze) The Fresh Prince dons a mafiaso suit similar to the one that Michael Jordan made famous in the NBA. Even in 1992 professional attire was baggy. 

8. Jumpman Tracksuit 

Episodes: 8, 9 

Retro Jordans always end up being a blood bath of frustration for consumers and slander to the retailers when their site crashes from the high demand. The Fresh Prince's tracksuit from the two-part episode could do the same kind of damage if Jordan Brand decided to bring it back. Shouts to Kadeem Harrison, Quincy Jones, Al B. Sure, and Bo Jackson on the cameos too — Will Smith had all the connects. 

7. Yellow Tuxedo and Air Jordan IXs

Episode: 93 

Suit and Tie shit was more Smith's Men in Black move but when his dude Jazz was getting married he stood up as best man in a tuxedo that wasn't quit as memorable as Dumb and Dumber but that pale yellow coat and Jordan IXs was one of The Fresh Prince's standout moments. We'll let you decide if that is good or bad. 

6. Morehouse Sweatsuit and Nike Air Bound 

Episode: 83 

The Fresh Prince knew what was hot in the streets and in the 90's reppin' Morehouse was a major hip-hop move whether you enrolled for a class or not. He may not have visited the campus on the show but something tells us Will Smith knew a few co-eds at the school personally. 

5. Varsity Jacket and Flannel Shirt Tied Around The Waist 

Episode: 81 

In season four Will continues to mature the style and the loud colors started to die down. During a power struggle acting like Ashley's protective older brother we get a shot of Will in a fitting grey and black varsity jacket and a flannel tied around his waist. Twenty years later, numerous rappers have been rocking the same exact thing. 

4. Paisley Blazer and Snapback 

Episode: 7 

Private school life can really constrict individuality in a fashion sense but that didn't stop The Fresh Prince from trolling the border of appropriate and detention with his attire. His paisley blazer and snapback hat were the go-to move for the his Def Poetry Slam—best school uniform ever? Definitely.

3. Randall Cunningham Jersey, Snapback, and Nike Air Flight '90 

Episode: 7 

It was moments like this that inspired Mitchell & Ness to bring back the retros a decade later. Few jerseys command as much respect as the throwback home Randall Cunningham Eagles jersey that Smith rocked on air along with the matching snapback and Flight '90s. So dope that it wouldn't be too much of a reach to see kids emulate the style head-to-toe today. 

2. Lime Green and Yellow Striped Tee, Pushed Up Baseball Hat, Air Jordan Vs

Episodes: 1, 24 

Will kicks off the show making a fashion statement from the jump — as soon as he pulls up to Bel-Air his lime green and yellow tee, matching cap, and Jordan Vs are far from the sartorial ways of the upscale community where his extended family stays. It doesn't take long for his Philly street cred to wear off on his little cousin Ashley and the original Fresh Prince outfit became a movement for young males everywhere thanks to the shows mainstream status. 

1. Urban Prep Tuxedo and Air Jordan Vs 

Episode: 1 

In the first episode the Banks' are throwing a black-tie event at the crib and instead of a traditional tux, Will decides to remix the classic attire by going with his own impromptu tuxedo with a graphic tee and bow-tie. The clean Jordan Vs sans any laces really set off the whole steez, no-f*cks-given.