The Greatest Fashion Week Street Style Looks of All Time

by Elinor Block

For a long time now, fashion week hasn’t just been about the people wearing the clothes on the catwalk, but it’s been just as much about the people off the runway too. Unless you’ve attended a fashion show, it’s really hard to grasp just how much of a circus whole street style thing is, and while the legendary Suzy Menkes might dislike it, I’ve come to accept that it is part of the fun of fashion week and a joy to see so many people enjoying fashion.

Arguably started with the likes of the late great Bill Cunningham and then continued by Scott Schuman’s Sartorialist, Tommy Ton and Phil Oh, it really kicked up a gear over the past 10 years, in part, thanks to Instagram. But that would be putting it too simply. While there are now scores of people posing outside fashion shows, there are the OG fashion bloggers who began in the late 00s or 10s are the ones who you now see on every fashion website. From Man Repeller’s Leandra Medine to Susie Bubble (aka Susie Lau), street stylers have become stars in their own right and are now sat front row at the biggest shows—from Chanel to Versace to Louis Vuitton and every other big fashion show you can think of. 

Instagram, however, has just ensured that street style stars are given even more coverage and even more of a platform, which means street style images, especially those of the past few years have become indelible. Speaking to Vogue in 2016 about street style, Ton revealed: “When you’re able to see fashion on a face that’s more relatable, it’s not manufactured, so it feels more accessible. I think that’s why street style blew up. Everybody loves beautiful models, but it’s when there’s a personality behind it, that’s when the look comes to life.”

With that in mind, and especially as we enter a very different kind of fashion week, here are some of the most memorable street style images from recent years…

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Style Notes: Anna Dello Russo outside the Drio show in February 2014, wearing a coat and boots from Tom Ford and a bag from Gucci.

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Style Notes: A black leather jacket layered over double denim and a checked shirt is classic Leandra Medine. Worn during New York Fashion Week in 2013. 

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Style Notes: This gorgeous dress by Maggie Marilyn was worn by editor Elaine Welterworth during September New York Fashion Week in 2018. 

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Style Notes: The always chic Australia Vogue editor Christine Centenera wears a Balenciaga jacket, skirt and shoes outside the Valentino show during Paris Fashion Week in October 2016. 

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Style Notes: There's no mistaking that this is a Gucci dress worn by Anna dello Russo in September 2016 in Milan. 

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Style Notes: In 2017, the Hadid sisters were suddenly everywhere. Bella loved outfits such as this skin-tight head-to-toe black look.

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Style Notes: It's not always over-the-top, look-at-me vibes during fashion week. Sometimes, it's just a great outfit that you can imagine wearing yourself. Julia Dalia is seen wearing a black suit jacket by Acne Studios, a Lacoste green longsleeve top, Flippa K trousers with a Calvin Klein belt, a Jacquemus mini bag in October 2019. 

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Style Notes: One of our all time favourite street stylers Giovanna Battaglia is seen wearing an all-red outfit in Paris in 2019. Those Prada heels are everything. 

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Style Notes: Susie Lau always makes the most of fun and interesting silhouettes. Here she is in 2017 wearing Molly Goddard, way before the designer was spotted on Villanelle. 

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Style Notes: While it's usually bloggers and influencers who are snapped outside the shows, sometimes the A-list will be spotted too. Naomi seen outside during Paris Fashion Week in October 2017.

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Style Notes: Another regular on the street style circuit, Emili Sindlev knows how to do colour clashing. Here she is in October 2019 during Paris Fashion Week.

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Style Notes: Arguably one of the most-snapped of them all, Olivia Palermo's outfits have graced many a street style gallery. In 2016 during Paris Haute Couture Week, OP wore these high-waisted trousers paired with a gilet. 

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Style Notes: Another one of our favourites, Tamu McPherson always look incredibly cool. Here she is outside the Chanel show last year. 

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Style Notes: There's something about the layering of the floral dress over the graphic print tee that gets us. Yasmin Sewell during London Fashion Week in in February 2017. 

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Style Notes: I still think about this Tibi dress a lot. During New York Fashion Week in February 2018, I spotted it on so many street stylers and it still looks good today.

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Style Notes: Ah, Mossy. There's no doubt she will always be extremely cool. Outside the Dior Homme Menswear Spring Summer 2020 show on June 21, 2019.

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Style Notes: While this look is very 2020, I couldn't stop thinking about this Prada outfit after seeing it on model Winnie Harlow in September 2019. 

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Style Notes: Another one of the classic street style set, Charlotte Groeneveld poses wearing a Chanel bag, jacket and shoes outside the Chanel Haute Couture show in January 2016. 

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Style Notes: Tiffany Hsu looks super chic in this blue suit with Bottega Veneta accessories in February 2020 during Milan Fashion Week. 

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Style Notes: The most fabulous frock and JW Anderson bag as seen on Giovanna Battaglia outside Emilia Wickstead during London Fashion Week September 2017 .

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Style Notes: Fun, '70s vibes from Tamu outside the Sacai show during Paris Fashion Week, September 2019.

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Style Notes: The effect one editor has on how we wear clothes can be seen in this one image: Vogue's deputy editor Sarah Harris wore this oversized belt/corset look during New York Fashion Week in September 2016 and everyone else followed suit. 

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Style Notes: One of my person favourite looks from the past few seasons is this Celine dress paired with chunky sneakers. As seen on Caroline Daur during September Paris Fashion Week in 2017. 

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Style Notes: Who What Wear's editor-in-chief Hannah Almassi wearing a gorgeous red Rejina Pyo dress during London Fashion Week September 2018.

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Style Notes: Scandi influencers Jeanette Madsen and Emili Sindlev wear clashing colours during Stockholm Fashion Week in 2018. 

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Style Notes: VB looking amazing during Men's Fashion Week in January 2019. 

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Style Notes: These Balenciaga boots were everywhere in 2017 and led to a host of sock boot copycats. 

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Style Notes: The Gucci belt bag became a must-have street style item back in 2017. 

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Style Notes: This outfit, as seen on Camille Charrière, made me (and everyone else in fashion) want to try the fishnet socks and trainers look. Spotted at New York Fashion Week in February 2016.

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Style Notes: Alexa Chung is always great at the street style thing. Outside Stella McCartney, during Paris Fashion Week, October 2017.

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Style Notes: Eva Chen is a fashion week veteran so she knows what's best to wear when running around the shows. Here she wears a Chanel jacket with jeans and black mules outside the Chanel show during Paris Fashion Week, March 2019.

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Style Notes: No street style round up could be complete without Pernille Teisbaek. These heel-strap leggings spotted here made everyone want to go out and buy a pair. From London Fashion Week, September 2016. 

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Style Notes: Kate Foley knows how to wear trainers and dresses together. During London Fashion Week in September 2016 she wears a floral dress with a pair of classic Vans. 

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Stye Notes: You've got to hand it to Pandora Sykes, she knows a trend before it becomes a trend. Here she is doing the oversized collar look in February 2019 during London Fashion Week before we all became obsessed with them in 2020. 

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Style Notes: Veronika Heilbrunner wears a gorgeous floral frock with a shearling jacket and Converse during Paris Fashion Week, Haute Couture January 2016.

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Style Notes: Denim and denim is always a good idea. Here's Chrissy Rutherford seen outside Chanel during Paris Fashion Week, October 2018.

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Style Notes: Vogue's fashion accessories editor Donna Wallace wearing an Ashish handbag during London Fashion Week, September 2017.

Next up, the biggest autumn/winter 2020 fashion trends to know. 

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