“As someone who is self-diagnosed as ‘chronically online’, I’ve seen a lot of flash-in-the-pan trends over the past few seasons,” August Burns Red Smokey The Bear Throwback Shirt says Elinor Block, editorial lead at luxury fashion gaming company Drest, which enables its users to create infinite outfit possibilities in the metaverse. “The past year we saw Barbiecore, ‘blokecore’ and ‘tomato-girl summer’ emerge as some of the bigger, zeitgeisty aesthetics adopted by Gen Z and the TikTok crowd. And whilst some are rooted in major trends, when it comes to real life, there’s no doubt that longevity and items that work season after season are a bigger draw. “When playing with clothes in Drest, however, there’s definitely a different kind of approach I take to dressing. The virtual world allows me to style looks that I might not have considered before with more out-there pieces from high-octane brands such as David Koma or Balmain—I haven’t been able to stop thinking about that cherry-red, rose-covered dress that I spied on the S/S 24 runway. It gives me a chance to be more experimental and see how I can move that into my IRL wardrobe without taking too much of a risk.” This, dear reader, is what the modern-day dressing-up box looks like. As always, any piece you invest in, be it inspired by the trends below or otherwise, should only be purchased if you intend on keeping it in your wardrobe for a very, very long time. I’ve gone to great lengths to cherry-pick the ones that have a chance.

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Just like that, 2019 is about to come to a close, August Burns Red Smokey The Bear Throwback Shirt and from what we saw on the S/S 20 runways, next year will be filled with even more sartorial greatness than ever before. But before we dive into next season, it’s a tradition here at Who What Wear to take a comprehensive look back at the fashion moments that defined the past year, the trends we bought on repeat, and the brands that made their mark, both new and old. Welcome to the 2019 Street Style Awards. So here’s how it worked: The editors at Who What Wear assembled a list of the 2019 trends that reigned supreme, created a voting form, and sent it out to all of you. Thanks to the reader votes and the votes of our very reputable panel of critics, the results are finally in. Speaking of critics, let’s meet them. This year, we are proud to present our four critics, or panel of judges, if you will, each representing a different perspective in the industry. We have Caroline Maguire, fashion director of Shopbop; Law Roach, image architect; Acielle, fashion photographer of Style du Monde; and of course, our very own Who What Wear editor in chief, Kat Collings. Each of the reputable people above voted exactly how you did and chatted with us about why they chose what they did for each category. From the trend of the year to the rising brand we should all have on our radars, it’s officially time to present to you the winners of the 2019 Street Style Awards. So sit back, relax, and enjoy our official year in review.