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 (i.e. one that's pretty much non-existent), here are some of the best street style outfits from recent years…

best street style outfits: Anna Dello Russo outside the Dior show in February 2014

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

best street style outfits: leandra medine wearing a black jacket

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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.

best street style outfits: elaine welterwerth wearing a white maggie marilyn dress

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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.

best street style outfits: christine centenera wearing balenciaga

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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.

best street style outfits: anna dello russo wearing gucci

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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.

best street style outfits: bella hadid wearing an all-black leather outfit

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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.

best street style outfits: giovanna battaglia wearing all red

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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.

best street style outfits: susie bubble in molly goddard

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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.

best street style outfits: naomi wearing a black jacket over a printed outfit

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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.

best street style outfits: emili sindlev wearing a red jumper and pink trousers

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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.

best street style outfits: olivia palermo wearing a gilet with blue jeans

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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.

best street style outfits: tamu wearing two-tone boots

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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.

best street style outfits: yasmin sewell wearing a floral dress, vetements boots, grey coat

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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.

best street style outfits: that yellow tibi dress being worn at new york fashion week

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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.

best street style outfits: kate moss outside dior

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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.

best street style outfits: winnie harlow wearing head-to-toe prada

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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.

best street style outfits: tiffany hsu wearing bottega veneta

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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.

best street style outfits: tamu mcpherson in a super cool oversized red fluffy coat

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

best street style outfits: vogue's sarah harris wearing a blue shirt and corset belt

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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.

best street style outfits: caro wearing a celine dress and a black clutch bag

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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.

best street style outfits: hannah almassi wearing a red dress by rejina pyo

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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.

best street style outfits: jeanette madsen and emili sindlev wearing colourful block colours

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

best street style outfits: victoria beckham during mens fashion week

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

best street style outfits: street stylers wearing those balenciaga floral boots

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

best street style outfits: gucci belt bag on a street styler

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

best street style outfits: camile charriere wearing a loose-fitting trousers and brightly coloured pink bag

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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.

best street style outfits: alexa chung wearing a checked skirt suit

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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.

best street style outfits: eva chen wearing a chanel jacket and a pair of chanel shoes

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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.

best street style outfits: pernille teisbaek wearing a blue jumper and stirrup leggings

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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.

best street style: pandora sykes wearing that ganni oversized collar shirt

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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.

best street style outfits: veronika heilbrunner wearing a slip dress, Converse and a shearling coat

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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.

best street style outfits: chrissy rutherford wearing a double denim outfit

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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.

best street style outfits: vogue's Donna Wallace wearing ashish

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

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