The Best 'Fresh Prince of Bel-Air' Outfits to Take You Back to the 1990s

Many of the show’s looks continue to serve as inspiration for current trends (because we all know 1990s fashion truly never goes out of style), and because it remains such a heavily searched topic, we figured we’d dive into what we personally consider to be some of the best fashion moments from the series. So if you’d like to take a minute, just sit right there, and we’ll tell you how they became the prince and princesses of a town called Bel-Air.

This was one of Will’s signature looks in the early 1990s episodes of the show. A ballcap tipped very upward (which oftentimes came in vibrant neon colors), a striped t-shirt, and basketball shorts that rivaled the ones NBA players were wearing back in the 1970s. Will donned this look quite a bit, but the green and blue pairing is our favorite. And while this picture doesn’t show Will’s shoes, he was more than likely wearing a pair of Nike’s.

You might look at this suit in 2023 and laugh, but in the 1990s this was very much a look. The same way Jalen Rose thought he absolutely nailed it with his Draft Day outfit (sorry Jalen for catching a stray), Will very much thought he nailed it with this fit (which is solidified by him trying to talk to a girl). The floral suit jacket paired with the striped tie remains an all time Fresh Prince favorite, and a departure from the street/athletic looks that Will usually sported on the show.

Honestly, there can be a whole separate article devoted to Hilary’s looks (which we will do one day), but this look right here is just one of dozens that Hilary Banks absolutely crushed during the show’s six year reign. The same way men always looked forward to seeing what Will was going to wear every week, women tuned in to see what Hilary was wearing every week as well. Hilary Banks never stepped out of the house looking anything other than photoshoot fresh, and that alone makes her one of the most fashionable television characters of all time.

Will and DJ Jazzy Jeff were definitely on to something when they put this fit together for Carlton. The uber colorful shirt, the chain, and bandana, had Carlton looking like he was going to audition for the fourth spot in Bel Biv Devoe. Also, we had to shout out Will’s fit in this episode as well. That bomber jacket was classic 1990s at its finest. As for DJ Jazzy Jeff, his outfit was kind of dope as well. Simple but still dope. The real standout though remains his black sunglasses which were a part of his signature look.

First things first Rest in Peace Uncle Phil. Most of the time when you saw Uncle Phil he was in the most dashing of suits, blazers, and formal tops, which were also dry cleaned and ironed to perfection without a single wrinkle in sight. Looking at Uncle Phil it isn’t hard to see why Carlton dressed the way he did because his father literally dressed the same way. For those that don’t know, Uncle Phil was a lawyer turned judge, so it wasn’t like he could show up to work looking any old kind of way. We’re saying all of this just to say that Uncle Phil’s style should be appreciated as well.

As for Willard, you could say that his style probably wasn’t always to his uncle’s liking, but we think Uncle Phil might have liked this outfit. A little bit of prep with the vest, and a little bit of street with the t-shirt and jeans.

Okay, back to the way Carlton usually dressed. Carlton was corny. Unbelievably corny at times, but that’s why we all loved him. It wouldn’t have made sense for him to dress in any other way than what he did because it suited him and his personality perfectly. Carlton had the male preppy 1990s look down to a T, and this is one of the examples of that. Carlton always looked spiffy in his suits, ties, and dress pants, so we absolutely have to give him credit for that.

We talk a lot about Hilary’s style, but Ashley’s fashion deserves a round of applause as well. At times she was a little more sporty and casual with the way she dressed (perhaps because of the influence of her cousin Will rubbing off on him), but it’s clear her sister Hillary was a major influence as well when it came to her preppy side. The episode “Grumpy Young Men” was a cool example of that with Hilary in an all-black get up, and Ashley in a long sleeve sweater tucked into a plaid mini-skirt. A fun sister style moment.

Will’s hoodie game was definitely on point during his Fresh Prince run, and you can’t deny the influence on the hoodies we see today. If you didn’t know any better you would think that is a 2022/2023 hoodie from Patagonia or Columbia. Very modern.

This right here is peak early 1990s couples fashion with Will rocking a very colorful sweater that he decided to tie overtop of his dress shirt, and Victoria Rowell’s character in the blue fitted turtleneck sweater dress with the dangling earrings. This is exactly how couples stepped out looking for their date nights in the early 90s (though we’re not quite sure if they were tying sweaters over their dress shirts like Will did here). Very stylish and on point.

We’re mostly focusing on Ashley here (sorry Carlton) because this was a really great fashion moment from her. The denim vest paired with the flowy colorful skirt and pocketbook (very 90s as well) was another neat style moment from her. One of the fun things about Fresh Prince lasting as long as it did was the fact that you got to see the characters evolve and grow over time. 

Let it be known that Hilary Banks was wearing blazer dresses long before the rest of us, and this baby blue blazer dress and tights combo from her was the perfect knock em dead combo.

Let it also be known that Hilary Banks was wearing skirts over top of pants a decade before that became a trend as well. We saw a lot of skirts over top of jeans in the early 2000s, and if we’re being completely real here, most of these looks were quite hideous, but as usual, Hilary pulled it off. If skirts over jeans ever becomes a thing again (hopefully it does not), we’ll have to look to Hilary for inspiration on how to pull it off nicely this time around.

We’re paying attention to Lisa Wilkes aka Nia Long here (the woman standing next to Will). Lisa also had some memorable style moments during her time on the show, including this one where you can see her with a denim vest over top a maxi dress. Shoutout to the short haircut too. That was thee haircut back then.

If you know you know. One of the greatest moments in 1990s television and by default, one of the greatest style moments in 1990s television.

And a little shot of Will and Carlton in ski wear to end it.