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13 Street Style 'It' Items to Watch Out For During New York Fashion Week

Babydoll dresses, padded headbands, Bermuda shorts and more!

Photo: Imaxtree

Although the Fashionista team has already been out and about at shows, parties and presentations for the past two days, Friday marks the actual, official start of New York Fashion Week. Here we go again!

While there will be plenty of trends to pick up on from the Spring 2020 runway collections, there’s just as much sartorial inspiration coming from outside, around and in-between the fashion show venues. After keeping track of this summer’s street style across Copenhagen, Couture Week in Paris, the music festival circuit and the menswear shows, we’ve compiled a list of what we predict will be the “It” items among the street style crowd in New York, as well as the rest of the fashion month. Read on to find out.

Padded Headbands

Padded headband. Photo: Christian Vierig/Getty Images

Hair accessories have become street style gold in the beauty realm, and why not? They likely catch more attention than any statement bag, and plus, they’re fun! From barrettes to hair clips, we predict padded headbands of all kinds — boasting embellished beading, bright colors and catching prints — will be the top choice among showgoers.

Boiler Suits

Boiler suit. Photo: Imaxtree 

The trending boiler suit is a godsend for fashion folks. Not only are they an easy way to achieve the majority of your outfit, but they’re extremely chic, too. They’re also highly versatile, which means there will be plenty of creative layering, accessorizing and styling to be had among boiler-suit enthusiasts.

Boxy Blazers

Boxy blazer. Photo: Imaxtree

Blazers were a hit over at Copenhagen Fashion Week in August, so, naturally, the tailored garment will likely take over the street style crowd in New York, with the silhouette leaning more towards big and boxy.

Bermuda Shorts

Bermuda shorts: Photo: Imaxtree 

And the piece we think showgoers will often pair with said boxy blazers are Bermuda shorts. Since pantsuits sound stuffy (literally and figuratively) to wear during this time of the year, opting for a longer version of shorts will likely be the stylish-but-still-polished alternative.

Pearl Jewelry

Pearl jewelry. Photo: Imaxtree 

Pearl jewelry has suddenly replaced fashion people’s collections of dainty earrings and pendants. Expect to see this shiny accessory in the form of statement earrings, layered necklaces, anklets and even as hair pieces.

Bucket Hats

Bucket hat. Photo: Imaxtree 

There’s a decent chance of rain over the course of fashion month, and a sartorial hack that we’ve learned from showgoers is to sport a weather-friendly hat — mainly bucket hats — in lieu of carrying an umbrella… all for the sake of enabling street style photographers to still capture their best shot of you, we presume.

Sporty (Read: Not Fashion!) Sneakers

Sporty sneakers. Photo: Christian Vierig/Getty Images

Perhaps it’s the now-considered-cool New Balance 990s that have conditioned the fashion crowd to have an affinity towards all types of sporty footwear. Instead of wearing the latest high-end brand’s attempt at designing a sneaker, we’re looking for comfort (a necessity for the week) over aesthetics from reliable sports brands. Think Asics, Adidas, Nike and Hoka One One.

Barely-There Sandals

Barely-there sandals. Photo: Imaxtree

The weather is still pretty warm in New York City, so the street style crowd can still take advantage of their favorite sandals before unearthing their boots for fall and winter. The barely-there sandal, comprised of minimal, very thin straps, has been a go-to item among fashion people this summer, so we expect them to be in full rotation — along with a fresh pedicure.

Small Shoulder Bags

A Gucci shoulder bag. Photo: Imaxtree 

The ’90s nostalgia trend is nowhere near dying down, and we think the small shoulder bag, which hangs just underneath your armpit, will be the vintage-inspired (or actually vintage) style of choice. Extra fashion points if the bag is covered in designer logos.

Zebra Stripes

Zebra stripes. Photo: Christian Vierig/Getty Images

The past few seasons have shown that the street style crowd loves a good animal print. So far, we’ve seen leopard and python motifs aplenty, but we have a feeling that zebra stripes (or similarly, tiger stripes) will be seen among a more-than-normal amount of showgoers, especially in bright and bold colors.

Babydoll Dresses

Babydoll dress. Photo: Imaxtree 

Gone are the days when floral-printed prairie dresses grazed the streets of New York city during fashion week. It’s time for the short-hemmed, ruffle-covered and sometimes-tiered babydoll dress to have its moment in the street style spotlight. Designers like Cecilie Bahnsen, Sandy Liang and Georgia by Kelsey Randall are creating some of the best versions favored by influencers and editors alike, and chances are we’ll see a few of them IRL over the next few days.

Bottega Veneta Shoes and Bags

Bottega Veneta’s the “Pouch” clutch. Photo: Imaxtree 

Another influencer favorite has been Bottega Veneta, as we’ve seen many pairs of the label’s shoes and handbags on our Instagram feed. The Italian luxury house has been revamped by creative director Daniel Lee, and it seems like the industry is smitten with the designer’s new take on leather goods. We’ve already spotted a few Bottega Veneta pieces among the street style crew over the summer, including the “Pouch” clutch and square-toed sandals, so we know they’ll likely make an appearance from New York to Paris, too.

Rectangular or Square-Shaped Sunglasses

Rectangular sunglasses. Photo: Christian Vierig/Getty Images

Tiny sunglasses whomst? It seems like the trend pendulum has swung over in favor of more rectangular or square-shaped frames, like Loewe’s trippy “Paula” sunglasses. They’re also now slightly oversized or just large enough to actually shield your eyes from the sun’s harmful rays: another example of how the reliable cycle of fashion trends keeps on moving along.

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