What Do Street Style Trends Look Like IRL?

Sometimes, Fashion Month can feel as much (if not more) about the crazy, over-the-top outfits showgoers wear as, well, the shows themselves. There's inherent fantasy in both: The runway represents the forefront of fashion, to be distilled for the masses as the months go by; street style, on the other hand, gives us a voyeuristic entryway into exactly how fun and expressive personal styling can be — even if we're not about to layer two jackets with three crossbody bags and Rihanna-level stilettos anytime soon.

This genre of photography has evolved greatly in the past century, largely due to the late Bill Cunningham and the emergence of independent blogs like The Sartorialist, which document the goings-on — and, most importantly, the clothing — of the exceptionally dressed. Naturally, as the audience of fashion grew, so did what the art form encompassed: an earnest celebration of individuality through style that came to be grouped with what can sometimes be best described as biannual mass peacocking (which sometimes involves a few outfit changes in a single day). There's merit in that, too — during Fashion Month, it gives us context for our favorite (often outrageous) runway pieces, and what they would look like in a relatively relatable context. (Couture on the sidewalk? I mean, why not.)

Sure, we may not be able to actually buy a majority of the clothes seen, but we can take away a few styling lessons that make our everyday looks feel that much more forward-thinking. And while purposefully wrinkled shirts may not be as much of a hit with your business-casual colleagues as they are with your fellow style-stalking friends — same with too-oversized pants, probably — there's no shame in experimentation. That's why we asked six intrepid staffers to put these trends to the test, with a little sense of humor and a goal not to have our garments interrupt our day-to-day plans. Below, we break down our interpretations of these larger-than-life pieces, how it feels to wear such statement-making items when you're simply going about your day, and how you, too, can take them for a spin without feeling totally ridiculous. (Seriously! We have the GIFs to prove it.)
Photographed by Alex Thebez of GIFRIENDS.
Photographed by Alex Thebez of GIFRIENDS.
Jacquemus Turtleneck Top, $399, available at Shopbop; Samuji coat; Nu New York pants (model's own); Topshop boots (model's own).

The Off-The-Shoulder Jacket
It's long been a joke within the industry that fashion editors don't know how to wear their jackets — well, it's not that they don't know, but they'd rather perch them on their shoulders like capes, allowing their hands to be free to text, Instagram, Snapchat, Facebook Live, or what have you. Then, a few seasons ago, we were introduced to Jacket Draping Level 2: slouching your jacket so that it's worn half-off the shoulder, or belting an oversized style at the waist, and letting the shoulders slouch around your arms. Fast-forward to fall '16, and Demna Gvasalia sends off-the-shoulder motos and puffers down his inaugural Balenciaga runway — and, like with anything he touches, not knowing how to wear a jacket became the trend to follow.

This trick is interesting, because it seemingly gained traction backwards: from editors to street style stars to the runway — as opposed to the typical reverse cycle. Its unique trajectory doesn't make it any less impractical, though. It's a style that requires constant readjustment, a particular posture, and enviable sweat resistance. So, we tasked fashion market writer Alyssa Coscarelli with the challenge. (On a balmy August day, no less. She's a trooper and a street style star in her own right, though, so she graciously complied.)

"I was admittedly pretty excited to try the forced-off-the-shoulder puffer-jacket trend, since it was the focal point of one of my favorite looks from Balenciaga's fall '16 show," Coscarelli says after the shoot. "But, I was nervous about how practical this trend would be IRL — and rightly so. As is the struggle with any off-the-shoulder piece, I ended up feeling like I had total T. rex arms, which means I could hardly swipe my MetroCard or hold on to the higher subway rails without totally throwing off my look. And, I felt like the forced off-shoulder manipulation made the coat jut out weirdly in the front instead of just laying flat."

"At the same time, though," she counters, "I felt super-chic. People were staring, but I was feeling this styling move. It may not be the most ideal in situations where you have to lift your arms or generally live life, but I still think there's something that looks so perfectly disheveled, yet editorial about this styling trick, especially over an amazing turtleneck, so I'm not nixing it from my fall and winter styling arsenal just yet." There you have it, folks: a solid not no.
Photographed by Alex Thebez of GIFRIENDS.
Photographed by Alex Thebez of GIFRIENDS.
Forever 21 Purpose Tour Graphic Hoodie, $24.90, available at Forever 21; Fenty Puma by Rihanna sneakers; The Life of Pablo T-shirt (model's own); J Brand jeans (model's own); bucket hat (model's own).

If we're talking about industry-sweeping trends, we need to talk about tour merchandise. For a while, it felt like all we were discussing: The Life of Pablo (Kanye West), Purpose (Justin Bieber), Revival (Selena Gomez), Lemonade (Beyoncé)...you didn't even need to attend a concert to get your hands on a branded T-shirt. (Better yet, find a pop-up.) It was a good year for music-licensing company Bravado, that's for sure. This quickly became about much more than memorabilia, though. "It’s important for an artist to break out of that idea of merch as a T-shirt, as a simple memento souvenir," Mat Vlasic, chief executive at Bravado, told The New York Times this summer. "At the end of the day, they’re driving the trends. They’re driving fashion." Sure enough, Bieber- and Pablo-tagged garments began appearing at various fashion events, on bloggers and influencers across the globe — a continuation of the larger influence of streetwear in fashion.

Now, I'm a notoriously late adopter of trends. Never mind that I spend most of my day writing about them: I'm a hesitant shopper and an indecisive spender, which means that by the time I convince myself that, yes, a choker might be worth it — boom, it's over. However, over the past few months, I've gradually accumulated various pieces of merch or otherwise celebrity-branded pieces — namely, a long-sleeved Pablo T-shirt and furry Rihanna Puma sandals. I didn't normally wear them outside of the house, though. (I saw these items more as memorabilia, by some weird, cost-ineffective logic.) So, for this challenge, I took it upon myself to pile on as much merch as possible, and try to be professional at the same time.

Granted, I work at a very progressive media company without a real dress code, so I already wouldn't face the issue of curbing HR-mandated dress requirements. Still, I felt pretty conspicuous walking around with a Justin Bieber hoodie tied around my waist, and having "I Love Kanye Like Kanye Loves Kanye" emblazoned across my back.

When we've seen merch crop up in street style, it's usually a singular item, with the fandom element distilled down with designer garments and more sophisticated staples. We're betting big on seeing more of these branded pieces across Fashion Month — and they'll likely look less hype-y when different tours aren't arbitrarily stacked together.
Photographed by Alex Thebez of GIFRIENDS.
Photographed by Alex Thebez of GIFRIENDS.
Ader Error Stripe T-shirt Long, $80, available at Ader Error; Mango pants and shoes (model's own).

Extra-Extra Long Sleeves

This time last year, fashion experienced a sleeve-lengthening phenomenon seemingly at every level: We dubbed them "spaghetti-sauce sleeves" when we saw them on the runway, and just straight-up impractical IRL. (Outside of the practical considerations of a desk lunch, how does a handshake or high-five go down when you've got so much fabric hanging down your arm?) It's one of those trends that looks great on the catwalk and in an editorial, but that we shrugged off as unrealistic. For the sake of an experiment, though, we baited senior fashion editor Erin Cunningham with the promise of a midweek burger and fries — as long as she consumed said meal while wearing comically long sleeves. There's no such thing as a free lunch, after all.

Here's what Erin had to say about it: "Spaghetti sleeves are not for people who like to eat spaghetti...or anything, for that matter. But I'm not totally against it. 1. It looks cool. (Seriously: As someone who stands at only 5-foot-1, I felt like the extra-long length actually made me look taller, even if that was only in my mind.) 2. They're fun. They're fashion. And you have to appreciate them for just that. They're not practical in the least bit, but, then again, are any of the best runway trends?"

Whether this is a "10/10 Will Try Again" trend, though, Erin's not so sure. "Maybe," she says. "It depends on the length — I'll likely stick to something that falls slightly below my wrist, but that also won't get dragged through a pile of ketchup. (This is a serious concern; I eat ketchup on everything.) Plus, since this style is 'in,' trips to the tailor are basically unnecessary — and who isn't all for a little money-saving when you can?"
Photographed by Alex Thebez of GIFRIENDS.
Photographed by Alex Thebez of GIFRIENDS.
Zara Gathered Tulle Dress, $39.90, available at Zara; Vans Embossed Stingray Slip-On, $65, available at Vans; Dune London Cat Ear Pom Pom Key Ring, $30, available at Dune London; Forever 21 jeans (model's own); Adidas Originals T-shirt (model's own); Skagen bag and watch (model's own).

The Daytime Ball Gown
No matter how many times we've seen her do it, Susie Lau of Style Bubble always tugs at our fashion heartstrings (and outfit dreams) when she breaks out a voluminous, tulle gown — à la Molly Goddard — and wears it over denim. She makes the outfit look so absolutely envious, we wonder why we relegate these party dresses to the barely touched "special occasion" sections of our wardrobes. There was only one person on our team who could do this trend justice: fashion market writer Ray Lowe, who has been known to hand over her credit card at the sight of any garment with cat ears and whose personal style can best be described as Whimsical Extra in a Classic Disney Movie. Naturally, she was game.

"I've been wanting to try this Susie Bubble trademark ball gown trend for a while now," she confesses. "The only thing stopping me was the justification of blowing cash on a pretty dress, just to wear it over a T-shirt and sneakers. But the finished ensemble made me feel really cool. Everything was just a bit over-the-top (slip-on Vans and tulle!) and street style ready."

For Ray, finally taking this on-trend plunge also involved a personal-style realization: how little she experimented with the contents of her closet — but how easy it was to actually execute. However, it wasn't all fun and games and #OOTDs. "By the time I stepped outside, every little breeze set the skirt flying," she says. "My main mode of transportation in the city is hopping on a Citi Bike, and I was reminded why I thought twice about trying this trend to begin with. Between getting the skirt stuck in the spokes and flying over my handlebars, there's a reason you've never seen anyone speeding past in a tulle dress before."

Still, she notes this getup was a compliment magnet. "We're a fashion-forward office, but the amount of kudos I received walking around in this look made it," she recalls. "It didn't feel too absurd and outside of my personal style: It has a sort of modern, punk-rock-princess vibe to it (just without the Avril Lavigne studded belt). While I'd probably exclusively be getting around in an Uber in it, I'd definitely try this trend again. My next take would be picking out a dress with a shorter and more structured skirt."
Photographed by Alex Thebez of GIFRIENDS.
Photographed by Alex Thebez of GIFRIENDS.
On Connie: Michaela Buerger Flowers Everywhere Long Sleeve Top, $340, available at Shopbop; Milly Modern Mini Skirt, $245, available at Shopbop; model's own sunglasses, bags, and shoes. On Alexandra: Michaela Buerger Flowers Everywhere Long Sleeve Top, $340, available at Shopbop; Carven Skirt, $290, available at Shopbop; All Birds Women's Wool Runners, $95, available at All Birds; Marc Jacobs Snapshot Colorblock Small Camera Bag, $295, available at Marc Jacobs; Dior sunglasses (model's own).

Matchy-Matchy Dressing
Last September, the statement piece to beat at New York Fashion Week was definitely Veda's Best Friend moto jackets, spotted on Caroline Vreeland and Shea Marie of Peace Love Shea. Soon enough, we began seeing a new wave of matchy-matchy dressing — one that involved pairing up, but not mirroring your partner. The idea is to coordinate on one piece or an overall formula for an outfit, and have each person interpret their own aesthetic within those parameters.

It sounds easy enough — but the challenge becomes straddling this line between cheekiness and the costume-y nature of overly planning your look. Luckily, fashion features director Connie Wang and senior fashion news editor Alexandra Ilyashov spend enough time together as it is, so this was a natural next step in their relationship. The result was only a tad bit creepy.

Connie went into this challenge a seasoned matchy dresser. "I'm no stranger to dressing alike (see: here), so matching with Alex was no big deal," she explains. "There's definitely a performative aspect to matching a friend in a way that actually feels very Hadid- and Jenner-approved — wherever Alex and I would go, people wouldn't only look and stare, but they'd do it with the kind of expectation that we were about to put on a show. The fact that we didn't have anything prepared was kind of a letdown." However, street style is a form of performance, she says — so it wasn't too far off: "It definitely makes sense that people would want to match a bestie. But for regular occasions, the pressure for showtime was too much."

Alexandra, for her part, was a little more hesitant. "Confession: I used to loathe having matchy outfits with my sister for family photos and/or as Hanukkah gifts," she admits. Since then, though, she's had a change of heart — and even kind of enjoyed twinning as an adult. "I got a kick out of walking around crowded, tourist-clogged City Hall Park, coordinated with Connie," she reflects. "Our chaste, high-necked, long-sleeved white shirts felt very 'just escaped the Victorian sanatorium in our (very chic) straightjackets.'" She concurs with Connie on the performative aspect of it all. "There was definite anticipation about what we were there to do, exactly, besides eat ice cream," she explains. "Some folks even whipped out their phones to snap a pic while the photographer was shooting — hey, it's the closest I've ever come to feeling like a B-list celebrity overseas."