The Comeback of the 90s’ Oval Sunglasses

Remember Hailey Bieber’s iconic Mia Thermopolis costume for Halloween that featured a stylish pair of 90s-style oval sunglasses? The Instagram post featuring the outfit went viral, and it’s even been rumored that a new Princess Diaries movie is in the works thanks to her!
 
If you’re a fan of these glasses yourself and have been searching high and low for a similar pair, look no further because today we’re taking a deep dive into this trend!
 
We’ll explore how this trend became popular in the first place, how modern fashion icons are bringing it back, and even recommend a few pairs to help you rock this trend.
 

How did the 90s oval sunglasses trend start?

 
After a long season of giant pairs in the 80s, the fashion scene was looking for a fresh change, and they found it in oval sunglasses.
 
The edgy, sleek shades were worn by almost every 90s it girl (and boy), from supermodels like Naomi Campbell to Hollywood stars like Brad Pitt and Gwyneth Paltrow. And what stars wear, the general public is sure to want a piece of.
 
The trend lived on well into the end of the decade, thanks to Keanu Reeves and his upturned shades in the first Matrix film, which was released in 1999.
 

90s celebs who kickstarted the oval sunglasses trend

Many have touted the 1990s as The Good Decade. The economy was flourishing, some of the most top-tier TV shows were released then, and world peace felt closer at hand due to the collapse of the Soviet Union in 1992.
 
Then, there’s the fashion, whose trends continue to be recycled and adapted to this day, like the one we’re talking about now. Here are some of the OG stars who made oval 90s sunglasses hella cool:
 

Brad Pitt & Gwyneth Paltrow

 
Since his rise to fame in the 90s, Brad Pitt has rarely taken a style misstep. Whether he’s got long or short hair, beard or no beard, the veteran actor has remained a heartthrob through the decades. And if there’s one accessory he looks good in, it’s a pair of sunglasses.
 
In the 90s, not only were he and former girlfriend Gwyneth Paltrow were twinning in terms of outfits and hair, they wore coordinating sunnies too, thereby setting the benchmark for couple sunglasses everywhere!
 
We can certainly take a few style cues from them, regardless of whether we have a Brad or Gwyneth on our arm or not: pair your oval sunnies with a casual tee in a neutral or striped vest and you can instantly channel 90s Hollywood chic.
 
If you like this pair, you may also like:
 

Keanu Reeves (à la the Matrix)

 
The Matrix movie trilogy popularized oval sunglasses, launching a fashion revolution offscreen. The distinctive eyewear has become synonymous with Keanu Reeves’s character Neo, as well as almost every other character in the movies.
 
Of course, you don’t have to choose between a red and blue pill to look like Neo. If you want to recreate this look, all you need are some sleek, black attire (preferably in leather) and a pair of micro oval frames.
 
If you like this pair, you may also like:
 

Chilli (from TLC)

 
Can you truly call yourself a 90s kid if you have never heard of TLC?
 
As one of America’s most successful girl groups, Chilli, T-Boz, and Lisa ‘Left Eye’ Lopes redefined fashion in ways no one could imagine (those overalls were such a hit). And no one made oval sunglasses look cooler than Chilli, who sported a myriad of pairs to match her ever-unpredictable outfits.
 
Make it spicy like Chilli and style your oval sunnies old school hip-hop style. Whether that means throwing on a pair of baggy jeans and a hoodie or a coordinated athletic tracksuit, it’s a throwback look that’s sure to turn heads.
 
If you like this pair, you may also like:
 

Modern trendsetters who have revived 90s oval sunglasses

90s nostalgia is back and here to stay, thanks to mega-influencers like Kendall Jenner and Selena Gomez.
 
Here’s how they have updated this trend to make it fresh and effortlessly chic:
 

Selena Gomez

 
Pop artiste, actress, and makeup mogul Selena Gomez is unofficially the queen of tinted shades, having been seen in one in almost every color. Even on her off-duty days, she manages to look effortlessly put together.
 
Through her many aesthetics, you can see that oval sunglasses are hugely versatile, whether you want to complement a grungy denim look or look chic and polished in a turtleneck and updo.
 
If you like this pair, you may also like:
 

Bella Hadid

 
While some may think that tiny sunglasses are a fashion faux pas, supermodel Bella Hadid has certainly turned the tide in their favor by wearing them pretty much everywhere. At events, she uses them to elevate her bold ensembles. Off the red carpets, she wears them to add more edge to her street style.
 
To work it Bella-style, pair your sunnies with an athleisure set or monochromatic outfit to transform yourself from basic to best dressed.
 
If you like this pair, you may also like:
 

Gigi Hadid

 
We can’t mention Bella without mentioning her equally stunning sister Gigi, as both have been key in bringing 90s oval sunglasses back in style.
 
However, you’ll rarely catch her wearing the same pair twice, as she once revealed she owned 200 pairs of sunglasses in 2018 — a number that has undoubtedly grown exponentially since then.
 
While Bella prefers an edgier, sporty look, Gigi exudes classy simplicity when she has her micro shades on.
 
To get the look, pair your oval sunglasses with denim for an everyday look, whether it’s a vest or slouchy jeans. You can also play up the sunglasses’ quirkiness by wearing a scarf with an interesting pattern or texture.
 
If you like this pair, you may also like:
 

Hailey Bieber

 
Hailey Bieber has mastered the art of dressing like a modern day princess, what with a Vogue photo shoot where she channeled Princess Diana and her viral Mia Thermopolis costume for Halloween.
 
As such, she’s given the oval sunglasses trend her unique glamorous touch, pairing them with dazzling bling, wavy chignons, and her signature slicked back ‘do.
 
To give your own look a Hailey makeover, coordinate your oval sunglasses with one of the aforementioned hairstyles and add some shine with minimalist yet impactful jewelry.
 
If you like this pair, you may also like:
 

Face shapes that can pull off 90s oval sunglasses

 
Before you pick out a pair, read on to see if you have one of the face shapes that shines the most in these 90s sunnies. Note that not everyone’s face shape fits into one category, so if you have a round face with diamond-shaped features for instance, you can still explore some of the tips below!
 

Square faces

 
Square-faced individuals like Brad Pitt and Gwyneth Paltrow have prominent wide jawlines and foreheads, which means thin and oval-shaped frames will help soften the angularity of their faces.
 

Diamond faces

 
Diamonds are forever and the same goes for how good you’ll always look in oval sunglasses! The diamond face shape is defined by a narrower forehead and wider jaw with high cheekbones, just like Robert Pattinson and Megan Fox. Oval sunglasses will complement your features and balance out your features.
 

Oval faces

 
If you have an oval face, congratulations! You’ll look good in any type of frame, including the same shape of sunglasses. Oval faces are distinguished by a wide forehead, high cheekbones, and a round jawline, which you can see in gorgeous starlets like Beyoncé and Bella Hadid.
 

Heart-shaped faces

 
People with this face shape will make hearts skip a beat when you don a stylish pair of oval sunglasses. The heart face shape features a broad forehead and a pointy chin, which oval frames will accentuate and balance out. This happens to also be Chilli’s face shape, which explains why she can make oval sunglasses work in any setting and with any outfit!
 
Interested in exploring other frames that can suit your face? Check out our guide on picking the right glasses for each face shape.
 

Confidence is still the ultimate accessory!

90s oval sunglasses may seem unconventional but trust us — as long as you have the confidence, you can pull off any look you want. So go ahead; bring back the 90s and express yourself through your style!
 
Loving the eyewear featured here? Check out more oval pairs from us, or keep exploring more celeb eyewear guides like our roundup of the most iconic sunglasses from movies!