Celebrity Couples in the ’90s Were Stylish, But These 5 are Even Better Dressed Than Jen and Brad
Sure, celebrity couples in the '90s and early '00s were well-dressed, but in recent times power couples have upped the ante. From Harry Styles and Zoë Kravitz to Justin and Hailey Bieber, these are the 5 best dressed couples in Hollywood.
Whilst we all have our own fashion obsessions, Matthieu Blazy’s Chanel, the wardrobe of Carrie Bradshaw or the perfect Prada shoes, if there’s one obsession that we all share, it has to be the style of celebrity couples. Although our fascination with not just the dating life, but the dress sense of famous people dates back earlier than any of us, the ‘90s was really a heyday and ultimate era of red carpet sightings and papped photos.
This is the decade that gave us Johnny Depp and Kate Moss (and Winona Ryder), Brad Pitt and Gwyneth Paltrow (and of course later Jennifer Aniston), as well as the much-adored JFK Junior and Carolyn Bessette Kennedy. It was also the era of rock and roll rebellion on the red carpet, in which Kurt Cobain and Courtney Love, Pamela Anderson and Tommy Lee and Angelina Jolie and Billy Bob Thornton all reigned supreme.
Nowadays though, whilst these couples no longer remain, our interest still does. Some of the styles are effortlessly cool (looking at you, Harry and Zoë), others turn it out with either matching red carpet ensembles or have their own taste. Whether they be on the on the streets, at the Oscars, at the airport or in the crowds at Glastonbury, one thing will always be true: we can’t get enough of celebrity couples style. I’ve taken a very deep dive into the Getty archives and have decided that these 5 are the best dressed modern day couples, the question is, do you agree?
The 5 Best Dressed Celebrity Couples in 2026
Harry Styles & Zoë Kravitz
Style Notes: Starting pretty obvious here, given that they just announced their engagement, but it’s not the ring or their wedding plans that enthrals me most about Harry Styles and Zoë Kravitz, it’s their outfits. Whilst Harry has long been known for his flamboyant, colourful and often quite kitschy style, wearing checked blazers, vibrant knitted tank tops and high-waisted trousers, it seems dating Zoë has had an effect. Turning into the ultimate ‘Brooklyn boyfriend’ his style has become much more pared back. Like her, he’s been seen in oversized wool coats and low-waisted jeans with Samba trainers and vintage graphic tees. Special mention also to the retro wrap-around shades.
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2. Dua Lipa and Callum Turner
Style Notes: Also engaged, Dua Lipa and Callum Turner are potentially London’s best dressed (and hottest) couple. Of course they turn out ‘fits far beyond the UK, often spotted on the red carpet, in L.A. as well as posting on social media. Carrying quite a classic ‘London’ aesthetic, Dua and Callum will often dark clothing, and definitely have a leather jacket (or 4) in their wardrobes—case in point: see photo here! Whilst Callum often toes the line of casual-cool, Dua has a slightly more experimental Y2K style. Think polka dot bikinis, capri pants and gingham corsets in summer.
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3. Rhianna and ASAP Rocky
Style Notes: Amongst a sea of celebrities donning quiet luxury minimalism and vintage casual sportswear, there has been nothing more refreshing than watching ASAP Rocky and Rhianna’s style evolution over the 5 years they’ve been together. Much more colourful and adventurous, Rhianna is known for her ability to mix high and low, sexy yet casual like no one else. (I mean, who else could get away with pairing a bare leg and strappy heeled sandal with a sports jersey and a Miu Miu ski glove?) ASAP’s style is just as well-noted. Blending high luxury with streetwear, he is one of the best dressed men on the planet, and has just signed himself a Chanel partnership. Not bad, huh?
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4. Hailey and Justin Bieber
Style Notes: Justin and Hayley Bieber are known for having different different. Anyone remotely interested in the duo will know she’s the OG clean girl and was a pioneer of the L.A. girl version of quiet luxury, often styling oversized blazers and coats, style with denim on bottom, loafers and a basic slim-fit tee or tank top. He however, is much less ‘clean-cut’, often seen in oversized tailoring, sports tops with jorts and a cap. They are *that* couple, though, and we love them so!
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5. David and Victoria Beckham
Style Notes: I couldn’t talk about the best dressed celebrity couples and not talk about Posh and Becks. Victoria Beckham’s eponymous label was founded almost 20 years ago, and he has partnered with multiple luxury brands such as Boss, Kent & Curwen, Belstaff, Calvin Klein, to name a few. Every event they attend, be it Wimbledon, the World Cup or the red carpet, they appear suited, booted and notoriously elegant. In the early noughties before all of this though, they were the pioneers of Y2K style when he played for England. Puffer jackets, leather two-pieces, brow slits and Burberry plaid were a regular occurrence, which were... Erm, a different type of elegance. Lest we forget!
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Rebecca Rhys-Evans is a London-based fashion and beauty editor with a decade of editorial experience. She started working at Who What Wear UK in the summer of 2022, where she was hired to lead all branded content for the UK site. Be it styling the latest designer collections, or reviewing the most recent beauty skincare products, Rebecca is the voice (and often face) for Who What Wear UK’s commercial partnerships. A self-confessed internet obsessive, she loves all facets of content creation—be it writing, filming, art directing or styling—and revels in collaborating with brands to help harness their product and tell their story. Before Who What Wear, Rebecca contributed to FLANNELS.com, BURO., Polyester, Screenshot, Marie Claire, Refinery29 and Culture Trip, reporting on everything from internet culture, sustainability and trends.