Predicted: These Will Be NYFW’s Biggest Street Style Trends

Cornel Cristian Petrus/Shutterstock

New York Fashion Week kicks off this week, which warrants making mention of what you can expect. First, designers will be showing their Spring/Summer 2020 collections, which, if last season's inspiring assortment of standout trends, splashy runway moments, and unexpected supermodel guest appearances are any indication of what's to come, are gonna be good. Second, New York Fashion Week street style is coming, and your Instagram feed is about to shift gears — big time.

If you follow brands, fashion editors, stylists, influencers, or all of the above, then the next several weeks will be tantamount to a digital fashion tidal wave. If you live and breathe street style, then brace yourself because a fresh batch of bookmark-worthy outfits is about to crop up. These outside-the-show looks are a benchmark of the season's biggest trends to come, which is why turning to a few industry experts for predictions on what to look out for is well-advised.

Ahead, hear from editors, fashion directors, buyers, influencers, and even a street style photographer on what NYFW street style trends are going to dominate this season (and, subsequently, what items you should be adding to cart in the weeks to come). Enjoy their advice, and outfits inspired by it from the comfort of your own home — no posing necessary.

The New Power Pairing

Fall is all about new outfit combinations and for Moda Operandi's Fashion and Buying Director Lisa Aiken, it's all about polish. "For New York, I always envision seeing a lot of tailoring. This season, the power pairing will be a blazer and shorts," she tells TZR. "It is an easy, current transition from summer to fall."


If you live for an off-the-beaten-path footwear trend then you'll be pleased to learn "clogs will back again this fall in all of their glorious, chunky fashion," Vogue E-Commerce Editor Julie Tong tellz TZR. "Taking a cue from Alessandro Michele’s Gucci clogs circa 2015 to 2019's western, cow print versions by Tory Burch, clogs are no longer reserved for Park Slope moms, but will spotted on street style stars and soon, inside your closet, too."

Leather Weather

Cornel Cristian Petrus/Shutterstock

Another prediction of Moda Operandi's Lisa Aiken is versatile and timeless: leather. "Real or faux, leather is continuing to have a real moment," she tells TZR. "As a personal form of power dressing, the appeal of the fabric lies in its slick, cool feel. Nanushka’s vegan leather pieces are sure to be spotted on the street ... on myself included."

Photo-Ready Prints

Style du Monde

If there's one type of individual who's bound to accurately predict street style trends it's a street style photographer. Acielle from Style du Monde shares her and her team "saw a lot of prints on the catwalk during the Spring/Summer 2019 season, so I'm definitely looking forward to seeing and capturing prints like tie-dye and acid wash on the streets. I've always loved the psychedelic vibes of tie-dye. It'll be fun to get them in my camera frame."

Oversized Dresses

Another way to let your outfit stand out is by playing with silhouette and proportions. Who What Wear Editor Allyson Payer admits that "NYFW is a little tricky because everyone wants to wear the new fall trends but it still feels like summer. I think the compromise will be the oversized dresses that were everywhere at Copenhagen Fashion Week," she tells TZR. "Cecile Bahnsen's baby doll dresses are the holy grail but Ganni, Zara, and Staud also have excellent versions."

New Bottega

Every few seasons a designer overhauls a historic brand, adds a breath of fresh air, and subsequently creates a whole lot of buzz — such is the case with Bottega Veneta's Daniel Lee. “This fall I am prepared to see a lot of Daniel Lee’s Bottega Veneta on the streets of New York, London, Milan, and Paris," Bergdorf Goodman Fashion Content Editor Jessica Minkoff tells TZR. "From his square toe strappy sandals and mesh pumps ... even a certified jeans and kitten heels girl like me is coveting a pair ... to leather board shorts and little black dresses with sculptural necklines, the buzzed-about brand is on everyone’s radar and wishlists."

Popsugar Senior Fashion Editor Laura Lajiness shares this affinity for the newness that Bottega Veneta brings to the table. "[It's] sure to be all over the street style scene this fashion week — I've personally invested in a few pieces this season. Prepare for square-toe shoes, minimal bags, and the brand's signature hand-laced weave aplenty."

Color Play

Color trends have ruled 2019 thus far (think slime green, millennial purple, pistachio) and Teen Vogue Fashion and Beauty Editor Michelle Li sees no sign of this slowing down. "My prediction for this fall is that street style is about to get a lot more colorful. While there will still be suiting and tailoring ... as there always is ... outfits are going to get more colorful and daring with how these colors are worn together," she tells TZR. "I think [it] will become a lot less seasonal and last through the changing seasonal weather."

Tonal Dressing

Another approach to experimenting with color is wearing several tones of the same color at the same time — modern monochrome, if you will. Shopbop Fashion Director Caroline Maguire anticipates head-to-toe cognac to take over street style this fashion week. "I’m most excited about seeing lots of tinted reptile in both ready-to-wear and accessories, rich cognacs, and must-have belts," she tells TZR. "I love the idea of a vibrant pink accessory with a full cognac-tonal look and can’t wait to see how others rock the trend."

Sustainability Continues

Conversations surrounding how fashion can stride toward sustainability is bound to continue. Columnist, model, and Instagram influencer Jo Rosenthal is onboard. "My prediction for this NYFW is that a lot of designers will be going a more sustainable route. I think that deadstock fabrics will be shown more than they usually are and straightforward info about transparency will be shouted from every direction." Brands like Collina Strada and Chromat are favorites in the underground NYC fashion scene and Rosenthal predicts "fun patterns and silks" to make an appearance on the street style scene as well. "If I'm wrong you can sue me, but if I'm right you have to take me for a margarita," she quips.

More Bucket Hats

Grosescu Alberto Mihai/Shutterstock

Few other hat trends have exploded quite like the bucket hat, which is why Le Fashion's Jennifer Camp Forbes expects to spot more in the coming weeks. "'90s-inspired bucket hats have been popping up on a lot of under-the-radar It-girls, so I wouldn't be surprised to see them have a major moment during this season's street style circuit."