New York Fashion Week (NYFW) Fall/Winter 2025 set an innovative tone for street style, marking a distinct departure from the previously dominant oversized, monochromatic ensembles. This season, the vibrant streets of Manhattan and Brooklyn transformed into a runway of tailored silhouettes, vintage-inspired textures, and luxurious accessories that celebrated both femininity and structural elegance.

A significant takeaway from this year’s NYFW street style was the revival of ladylike dressing, a trend that many fashion insiders observed with enthusiasm. Influencers, stylists, and fashion aficionados gravitated towards classic, structured pieces, moving away from the slouchy, casual looks that had permeated the fashion scene in recent years. Notably, fashion photographer Phil Oh captured this shift perfectly, stating, “There was an air of sophistication this season that we haven’t seen in a while.” This sentiment was vividly illustrated through the prevalence of long, elegant leather gloves, impeccably tailored coats, and carefully curated accessories such as sleek skinny belts and sumptuous silk scarves that elevated each outfit.

At the forefront of this refined aesthetic was vintage enthusiast and influencer Jenny Walton, whose impeccably polished ensembles embodied the quintessential “Lady Who Lunches” style. Her outfits featured structured handbags made of rich materials, delicate yet bold silhouettes, and vintage brooches that added a modern twist to timeless elegance. Each of her looks resonated with the charm of classic fashion while embracing contemporary flair.

While the runway shows undoubtedly influenced Fall/Winter 2025 trends, it was on the bustling streets where fashion enthusiasts truly brought the season’s aesthetic to vibrant life. Among the standout looks, attendees were seen artfully buttoning up funnel-neck trench coats, cleverly styling them as chic dresses paired with strappy heels and meticulously chosen structured handbags. The use of skinny belts played a pivotal role in cinching waists and defining silhouettes, while brooches gracefully adorned the lapels of coats, blending vintage charm with a modern sensibility. This season reflected a harmonious balance between tradition and innovation, as fashion lovers creatively interpreted classic styles for a new era.