18 Iconic Will Smith Outfits That Summed Up the 90s

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Last Updated on November 30, 2021

No one does 90s fashion quite like the ‘The Fresh Prince’ himself.

Will Smith began his music and acting career in the late 80s, but gained recognition throughout the 90s. He’s considered one of the most iconic American TV actors of all time and is often used to reference the 90s.

During his life, Will experimented with various styles and looks of the era. He is known as a comedian, has a quirky sense of style, and has the ability to capture the attention of millions.

Will was only 21 when he began newly acting on ‘Fresh Prince of Bel-Air’. His outfits on the show, along with the ones worn by the other characters, were religiously copied and noted by fans. Throughout the years, Will was seen sporting all kinds of different looks. He has definitely taught us how to dress with swag.

Nostalgia Overload Alert:

Let’s take a look Will Smith’s most iconic outfits.

#1. Vertical stripes and backwards cap

This image seems to sum up Will Smiths’ personality; the original, sassy comedian of modern American television. While this photo only displays the top and cap of Will’s outfit, as viewers we get the idea.

This was without a doubt an outfit worn for his character on the TV show. The long sleeve, closed neckline, the colorful striped top is very reminiscent of everything early 90s. The fresh prince loved his backward baseball cap. The bright blue baseball cap is a nice touch, but the best part of this outfit is Will’s expression; it says it all!

#2. Oval sunglasses and bone colored jacket

Here is Will with his wife Jada-Picket Smith at a red-carpet event. Will is wearing a bone-colored, button-down blazer jacket paired with a black top and pants ensemble. What represents the 90s is the subtle pinstripe print on the top, the high waisted trousers, and the cool oval sunglasses.

This look is classic 90s. A more traditional take on an otherwise laidback time in fashion.

#3. Fur and leather

This look leans more towards the hip-hop scene that was prominent during the 90s. Will wears a thick gold chain necklace, a turtleneck black top and tucked baggy military green bottoms.

The look is completed with a heavy, brown leather winter jacket that is lined with cream-colored fur – a very typical style of the jacket during the decade. The color scheme is aesthetically balanced.

#4. Bucket hat days

This outfit is a clear description of the simple and casual style of the 90s. Will wears a teal-green tee, knee-length pleated shorts, sneakers paired with thick socks, and topping it all off with a black bucket hat.

The fresh prince wearing Jordans was a common event during the 90s. Within this particular outfit, there are multiple separate 90s trends paired together. The look is funky, casual, yet seems very comfortable. Will makes a peace sign with his hand at the photographer.

Check out:

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#5. Tracksuiting

Here Will is seen wearing a full out sweatsuit. The combination incorporates red and navy stretch pants, with a white tank top worn underneath. 90s tracksuits were all the rage. Will wears a 90s baseball cap backward and placed atop his head—not on his head.

The great thing about tracksuits are their versatility. Whether running on the track, running errands or even running late for a wedding (yes, really!). They were a staple part of the 90s.

#6. Acid wash overalls

Overalls are one of those things that people either love or hate. I love them.

They rose to popularity during the 90s and Will Smith was seen wearing them on various occasions for his role on the TV show. These are known as the fresh prince overalls, and they became iconic after appearing on the show.

The acid wash denim overalls with on strap undone paired with an african print button up loose shirt prove the fact that any type of fabric combination was acceptable during the 90s. The look is completed by a simple, black leather belt around the waistline. Hand in pocket not optional.

Read: 90s Men’s Overalls: Trends and Outfit Ideas

#7. Out on the town

A look fit for the night. Will is photographed wearing a black, shiny all over outfit featuring loose pants and a black button-down blouse. Smooth. The outfit features layering and the combination of gold and black is a timeless yet popular color combination during the 90s.

#8. Plaid harem

Plaid was one of the most popular prints during the decade. Will is rocking the trend with his black and white plaid 90s harem pants. His illustrated t-shirt matches the colors of the trousers, and he pairs the look with a pair of stylish Nike Jordans. While the look is casual, it does not compromise on style.

#9. Basketball casual

Will is casually sitting, wearing a very characteristic outfit of the 90s. A teal-colored t-shirt and mid-knee length shorts duo, white sneakers, and thick white socks. Very simple. Yet very representative of this decade in time. The white sneakers and socks help balance the teal color of the rest of the outfit, and they work well in combination.

#10. Candy striping

A candy striped baggy t-shirt, black sweat pants, black and white sneakers, and once again, thick white socks. The outfit oozes oversized casual. Typical 90s.

#11. Open collar shirt

Here Will is seen wearing a more sophisticated style option for a red-carpet event. The Will Smith suit is very 90s; boxy and oversized. He’s paired the suit with a mint green jacket, opened at the collar. This combination of suit and open-collar shirt was a popular option at formal events throughout the 90s, especially late 90s.

Read: 90s Men’s Suits: Get to Business with These Throwback Trends (With Iconic Photos & Styling Tips)

#12. Multicolor jacket on denim

A funky take on the 90s. Will is seen wearing a colorful bomber jacket depicting shades of purple, red, green, yellow, and orange. Picasso eat your heart out. He’s also wearing his classic, backward baseball cap, denim jeans, and chunky black combat boots. The jacket, denim, and shoes are all highly characteristic of the decade.

#13. African print with multi pattern shorts

This mix and match look is one of Will’s most expressive that he wore. While the purple and black are present in both the top and the shorts, they feature entirely different designs.

Will wears an awesome african print t-shirt, a yellow and blue baseball cap, this time facing forward, and mint green and black socks. An extravagant combination of prints—very representative of the late 80s and early 90s.

#14. Color block open shirt

An iconic look from the Fresh Prince of Bel Air TV show. Of all his looks I’d say this was Will’s attire on the everyday. A white t-shirt branding a graffiti aesthetic logo, a color-blocked open shirt on top, high waisted jeans, and of course—that backward baseball cap. The combination of yellow, purple, and green just makes this look so iconic of the 90s.

#15. Ski suit casual

Will wearing a ski suit. Out there, really out there. His ski suit is paired with a pair of black leather, lace-up combat boots. Very common footwear during the 90s.

#16. Orange and black leather jacket

In this look, Will pairs a high waisted pair of black trousers with a simple white button-up polo shirt. The funky addition is the orange and black leather jacket, which has a shiny top coat giving it a glossy finish. The jacket is a fun addition to the otherwise simple outfit. Orange became one of the trendiest colors during this time.

#17. Loose multi-print waistcoat

Here is Will once again sporting bright orange. This outfit consists of loose, dark jeans, worn with a neon orange t-shirt. The look is complete with a button-down vest slash waistcoat featuring color blocks of navy, grey, black, and a darker toned orange.

This outfit is very particular, and a clear representation of some of the less glamorous color combinations of the 90s. While the outfit is creative, it has simply too much going on. Only for the brave.

#18. A cream cardigan

My final outfit of choice is one that we didn’t see much of Will wearing in the 90s. Toned down colours and shaped. The classic black t-shirt, loosely fitting black dress pants, and a cream cardigan on top. The look is accessorized with a black leather belt and black leather shoes. A futuristic yet modern take on 90s fashion.

On thing is for sure. Will has a serious celebrity appeal with his outfits. His choices are diverse and fascinating.

Now, over to you. Which is you favourite outfit? Leave a comment below!