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The 2019 Street Style Awards: These Were the Biggest Fashion Moments of the Year

Just like that, 2019 is about to come to a close, 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. 

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Martin Schoeller/Getty Images/Style du Monde/Shopbop

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 ShopbopLaw 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.  

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The Style Stalker/Collage Vintage/The Style Stalker/The Style Stalker/Collage Vintage

Suiting might have won the Trend of the Year award, but following the success and longevity of suiting as a whole, it has officially become a wardrobe staple in closets everywhere rather than a fleeting trend. Tailored separates have now graced more runways, celebrities, and street style stars than we anticipated, and according to our readers, that is due to the fact that this trend is the “most wearable for everyday while still always looking chic.” If both the S/S and F/W runways taught us anything this year, it was that the industry is taking a drastic shift away from gimmicky trends and toward a more approachable way of dressing. Suiting is one of the most notable key players within that movement, as you can wear the pieces together or separate, not only giving you more bang for your buck but also rounding out your wardrobe.    

Who What Wear’s editor in chief, Kat Collings, is very on board with the suiting lifestyle. “All hail the suit. I can’t think of a trend that was more beloved this year by the fashion set,” she told us. Beyond the wearability of the trend, our readers are keen to partake in the style for reasons that dig even deeper. “I think it really puts a pinpoint on the androgynous way of dressing in the modern fashion climate,” says one reader. Women have officially reclaimed the power suit as their own, and there aren't any boundaries in terms of occasion, styling, or even price point. The shopping selection below will prove exactly that.

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The Style Stalker/The Style Stalker/Collage Vintage/Collage Vintage/The Style Stalker

At this point, it’s hard to imagine a time without Bottega Veneta, but then again, that’s what we thought about #OldCeline, and here we are. What I’m trying to say (without dragging you into the post–Phoebe Philo Celine depression) is that #NewBottega—run by Creative Director Daniel Lee—has only really been around for a little over a year, but the impact it has already had feels more iconic than ever. The amazing thing about this industry is that even the most settled heritage brands can make a new name for themselves, and thanks to what Lee did with Bottega, we now have a brand that filled the sartorial void that the loss of something as iconic as #OldCeline once occupied. 

All this industry talk might sound a bit niche, but on a more mainstream scale, this brand has created some of the most talked-about, -purchased, and -photographed items of the entire year—items even people who don’t really care about fashion at all might be able to identify. “Between The Pouch bag and the shoes, Bottega had a huge year. I saw people of all different styles wearing it,” said one of our readers. This means that while, yes, Rosie Huntington-Whiteley owns a small army of The Pouch bags, consumers of all calibers are buying into this brand, and they’re doing it with vigor. “Bottega Veneta for sure. Daniel Lee’s creations dominated the streets,” said street style photographer Acielle of Style du Monde, and since these are the street style awards, this winner seems beyond fitting. 

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Collage Vintage/Collage Vintage/Collage Vintage/Collage Vintage/The Style Stalker

Animal print happened to win Trend of the Year last year, and according to your votes and the votes of the critics, its popularity has yet to decrease. This year, however, we saw new animal prints get tossed into the mix like cow print and tons of zebra. The resurgence of animal print last year felt fresh, but now, according to Law Roach, it’s continuing to be successful “because it’s a neutral.” The fashion set taught us quite a lot this year about how to wear this print trend in a way that continuously feels forward and innovative, particularly with the rise of prints other than leopard.    

Two straight years of success not only within our Street Style Awards but with the industry as a whole has proven that this print trend is one that is well-liked and accepted by people all over the world and with all different styles. “Animal prints, especially leopard and snakeskin, are a fun way to add pizzazz to an outfit,” said a reader. Even if you’re wearing jeans and a T-shirt, something like snakeskin boots or a zebra coat can revamp your look in seconds flat. Suddenly, even the most basic of outfits becomes street style–ready.

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The Style Stalker/The Style Stalker/The Style Stalker/The Style Stalker/The Style Stalker

Considering the fact that Khaite was just founded in 2016, the journey of this brand thus far is quite remarkable. Founder and designer Catherine Holstein started the brand as an ode to American staples and all the classics that went along with it. Since its beginning, the brand has evolved into much more. Khaite’s first runway show in 2019 had every editor and buyer clamoring as one glamorous look after another came out. It was here that we were truly introduced to Holstein’s vision for the brand, and her S/S 20 collection was just the cherry on top. It’s rare that one major (and first-ever, might I add) runway collection can convince an entire industry that this is the brand to know, buy, and wear, but the elegance and drama of her last two collections had everyone drinking the Kool-Aid.

While the brand hasn’t quite reached the same status as Bottega Veneta, its trajectory over the last two years has proved that it is on its way to the very tip-top. “Cate Holstein of Khaite is creating such beautiful, showstopping pieces. The craftsmanship is absolutely impeccable and something that everyone can appreciate. My personal favorite is their denim—the fit and wash are flawless,” says Shopbop’s fashion director, Caroline Maguire. And that’s the thing about Khaite—buying into the brand is buying into a very well-curated wardrobe that will never go out of style. “From the jeans to the shoes, this is definitely going to be the next It brand in 2020,” said a Who What Wear reader. Yes, iconic pieces are already highly praised, such as those zebra boots and all of the noteworthy knitwear, but to be simultaneously recognized for the subtler items in a collection, like denim and poplin shirts, means this is a brand that is destined for success. 

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Collage Vintage/The Style Stalker/The Style Stalker/The Style Stalker/The Style Stalker

To no one’s surprise, Daniel Lee’s iconic The Pouch bag strikes again. The second it was released, it basically sold out. This cloud-like clutch quickly caught the attention of every influencer, celebrity, and fashion girl in existence. Even the savviest shoppers are still having difficulties nailing this designer bag down due to all the hype it’s generated. The unsurprising thing about The Pouch is that its owners love showing it off, and who wouldn’t? Whether it be on Instagram or in reality, this bag has claimed its rightful spot center stage in the industry, and all of your votes have formally confirmed that as we leave 2019, the roar of this bag will continue to sound.

If anyone knows how to identify the It items of the moment, it’s Acielle, street style photographer of Style du Monde. “I think I saw more Bottega Veneta bags during fashion month than any other brand,” she says, and as someone who travels to shoot the most iconic street style scenes in the world, this woman really knows what she’s talking about. Our readers also agreed full-heartedly with Acielle, and one said that “this bag was seen all over—on the streets, on the runway, and on celebrities. It's unique and should be able to carry all your essentials.” They’re right—for a clutch, The Pouch holds quite a lot and, as seen on the streets, makes any outfit look that much more notable. If you’re looking for a designer bag to gift yourself with this season, The Pouch gets all of our votes.

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The Style Stalker/Collage Vintage/Collage Vintage/The Style Stalker/Getty Images

The fact that a hair accessory won It Item of the Year means that when it comes to this industry, there really is no item too small to make a huge impact. Headbands have never really been “out” per se, but once fashion girls saw those puffy satin headbands come down the S/S 19 Prada runway, all bets were off. Coming in an assortment of candy colors, these pricey hair accessories sold like hotcakes, but spending almost $300 on a headband was not in the cards for everyone, and rightfully so. Naturally, other brands started jumping on the headband frenzy, and in the blink of an eye, these puffy hair adornments were pretty much all the fashion set cared about. “You know what they say: The higher the headband, the closer to [the fashion] gods,” Collings told us. “You’d be hard-pressed to find a stylish woman who didn't sport a velvet, silk, or satin headband this year.”

“It was refreshing to see padded pink and bold headbands this year. So youthful yet so chic,” said one of our readers. This trend was easy to wear and find at low prices across the board. One of the infamous fashion-girl hacks of 2019 was identifying a trend like padded headbands and scoring it on Amazon for under $10—see for yourself in the shopping selection below. According to the general manager of ShopStyle, Alison Stiefel, headbands have shown the biggest increase in searches on ShopStyle's site with a +14,100% spike. This means that although this trend has certainly dominated the market this year, shoppers are still spending on the accessory. So if you have yet to buy into it, the data show that it’s not too late.  

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The Style Stalker/Getty Images/Style du Monde/Getty Images/Style du Monde

Prada opened its F/W 19 runway show with the Monolith Boots. Complete with an exaggerated chunky lug sole, mini zippered compartments for—dare we say it—storage, and the overall combat-boot vibe we all know and love, it was clear these boots were destined for fame the moment they stomped onto the runway. This shoe was not only present throughout the rest of the collection, but sister styles also debuted and later went on to evolve into several other versions including the oxford and rain-boot pairs (see shopping section below). Not that we don’t love the other iterations of this major sole moment from Prada, but the knee-high Monolith pair was really something else, and the fashion girls of the world clearly agreed.

“The shape of the sole is so peculiar, and the tiny pockets create a totally new version of combat boots,” said one of our readers. Peculiar in a good way, of course, is typically what ends up encouraging the rise of any particular product, as it ignites curiosity and excitement in not only the wearer but the onlooker as well. This shoe is, according to celebrity stylist Law Roach, “so tough but so chic.” Thanks to the street style set, we’ve seen It girls and celebrities style the statement shoes in every which way, featuring, as Roach would say, looks that are tough but chic. This included easy dress-and-boot combos, styling the cool-girl shoes with jeans and a blazer, and much more. If the street style images above prove anything, it's that 2019 was the year a new Prada icon was born. 

That's all, folks. Hopefully, you've enjoyed this walk down memory lane as much as we did. But before you leave, be sure to check out some of the exciting new trends coming down the pipeline in spring 2020