90's Celebrity Outfits We'd Wear Today

Despite the younger generation thinking the 90's are long gone, past eras always seem to make their way back through fashion. Whether it's people today wearing vintage graphic tees straight from the 90's or old distressed denim jeans, everything worn now is influenced from the past.

With the rise in popularity of vintage fashion, we thought it'd be helpful to highlight celebrity outfits from the 90's that we wouldn't hesitate to wear today. 

Jennifer Anniston

Vintage 90's Jennifer Anniston

The 90's Friends star is the queen of outfits. You can't go wrong with this outfit with a backwards snapback hat, frameless shades and the tee shirt under the dress adds a final touch of detail.

Tyra Banks

Vintage 90's Tyra Banks

Does denim on denim ever go out of style? Tyra shows how effortless it is to pull off this look casually with leather cowboy boots and a hat.

Drew Barrymore

Vintage 90's Drew Barrymore

We love a good denim jacket, especially with some good embroidery like this Planet Hollywood jacket. Everything looks good with a pair of trousers and boots.

Tupac Shakur

Vintage 90's Tupac

Effortlessly cool. Tupcac shows that you don't need big graphics or branding for a good fit. This formal/casual look is something we'd love to be able to pull off. 

Britney Spears

Vintage 90's Britney Spears

Who doesn't love a tonal, layering look? Baggy parachute pants, plain crop top and a oversized overcoat is all you need for a good fit.


Vintage 90's Aaliyah

The oversized jersey look is back, but Aaliyah wore it first. The baggy on baggy looks works in certain cases, and this is one of them.

Princess Diana

Vintage 90's Princess Diana

Is it really a complete list if Princess Di isn't on it? The iconic graphic sweater, biker shorts and sneakers look is for anyone and everyone.

Adam Sandler

Vintage 90's Adam Sandler

Adam doesn't play around when it comes to his fits. A loud look that people could only wish to pull off today. We love the mix of colors in this one.

Brad Pitt

Vintage 90's Brad Pitt

A leather jacket is probably one of the timeless pieces of clothing you can own. Brad pulls off this simple look perfectly with a simple blank tee and trousers.

Denzel Washington

Vintage 90's Denzel Washington

A hat and blazer combo is something we love. Pair that with a perfect pair of denim and you can't go wrong. The perfect part is you can pair this with sneakers or a classier loafer depending on your vibe.

Johnny Depp

Vintage 90's Johnny Depp

Another blazer and hat look but we love how Johnny pairs it with a casual white tee to bring the look even more relaxed.

Woody Harrelson

Vintage 90's Woody Harrelson

A king of underrated fits, Woody pairs some New Balances we would wear today with a statement knit sweater that we're obsessed with.


These are just some of our favorite outfits from the past. Want to dress like them? Grab some authentic vintage clothing items from us sustainably online from anywhere! Click here to shop our ever-evolving collection!