Trends that dominated 2016 are firmly back in the forefront in 2026, creating nostalgic style moments from casual streetwear to the runway. This is an unexpected throwback to the past for fashion. The mid-2010s are being channelled by designers, influencers, and A-list celebrities with stylish modern twists, demonstrating that what was once retro is now surprisingly relevant.

2016 fashion — image @shutterstock

Famous wardrobe essentials like chokers, off-the-shoulder tops, baseball caps, and graphic tees pieces that flooded festival fashion ten years ago, are now redesigned for 2026 and are at the front of this comeback. To update these looks beyond their initial casual vibe, stylists advise wearing chokers with layered necklaces and off-the-shoulder tops with fitted pants.

Celebrities are actively participating in the throwback trend. Social media has erupted with a 2016 throwback challenge, seeing stars like Kylie Jenner, Lucy Hale and Eva Longoria revisiting flannel shirts, mirrored sunglasses and distressed denim, classic hallmarks of 2016’s carefree aesthetic.

Hailey Bieber in 2016 fashion — Image @Shutterstock

Royal influence hasn’t been ignored either. Princess Kate has inspired fashion fans by reviving her 2016 British Vogue cover look, particularly the suede trench coat, as a must-have transitional piece for the season.

High fashion is experiencing nostalgia as well. Many Spring/Summer collections pay homage to the spirit of the decade, embracing colorful accessories and streetwear influences that ruled runways ten years ago, even as designers continue to push forward.

Taylor Swift is seen walking in Soho on May 1, 2016 in New York City. — Image @Gettyimage

The return of 2016 fashion is more than just a throwback; it’s a sign of a renewed desire for carefree, expressive, and authentic style, and it serves as a reminder that fashion cycles are dynamic rather than static.

Ralph Lauren is more than a brand; it’s a style institution. For over six decades, the American designer has shaped what “classic cool” looks like, combining rugged utility, Ivy League prep, and luxury refinement into a singular fashion language. This fall, Lauren brought that legacy straight to the global stage with a highly talked-about Men’s Fall 2026 Collection presented at Milan Fashion Week, his first dedicated menswear show in years, and a clear sign that Ralph’s vision remains at the center of fashion.

Ralph Lauren Men’s Fall 2026 Collection — Instagram

The collection is like a story unfolding through the many ways men live and dress. At its core, Fall 2026 channels authentic American style, but with a lively, modern twist. Expect rough textures, deep earth tones, and simple, easy-to-wear tailoring that looks effortless but is carefully considered. Pieces range from vintage‑tinted rugby shirts with bold stripes to loose denim and classic camouflage, honoring the brand’s iconic Polo roots.

Ralph Lauren Men’s Fall 2026 Collection — Instagram

As the show evolved, so did the mood: Ivy League checks and regiment‑style coats gave way to solid wools, herringbone weaves, and forest greens. There’s a witty mix of workwear practicality and clean cuts, a checked suit paired with duck boots one minute, a plush camel cashmere overcoat the next.

Ralph Lauren Men’s Fall 2026 Collection — Instagram

Textures play a key role. Imagine leather jackets that have been worn in, suede jackets with fringe, soft fleeces, and intarsia knits that balance comfort and refinement, perfect for everyday wear. Oversized coats and baggy trousers bring a relaxed charm, rooted in tradition yet wholly fresh.

Ralph Lauren Men’s Fall 2026 Collection — Instagram

This season is different because refinement and relaxed style go hand in hand. The easygoing look of Polo and the crisp details of Purple Label come together to create an outfit that feels both true to the brand and as stylish as it would have been in the 1990s.

Ralph Lauren Men’s Fall 2026 Collection — Instagram

The Fall 2026 Milan Men’s Fashion Week kicked off on January 16 and will run through January 20, taking place in Milan, Italy. From day one, the event has brought together designers, industry insiders, and stars from the entertainment world. Guests like Colman Domingo and Nick Jonas, along with other celebrities, have been seen showing up in sharp tailored suits. So far, the street style outside has become one of the highlights of the show, alongside the runway presentations indoors.

Photographed by Acielle Tanbetova, guests outside the venues were seen in a variety of outfits, but one thing many had in common was jackets and coats. From long overcoats to tailored jackets and trench coats, outerwear played a major role in men’s styling this season, influenced by the winter weather in Milan. Some layered knit sweaters over tailored suits. Others leaned into a more casual look, pairing jeans or plain trousers with coats or leather jackets.

Photographed by Acielle / Style Du Monde

Neutral palettes were popular across many outfits, with shades like grey, brown, and beige. Deeper colors like dark burgundy appeared in suits and paired with black coats, adding contrast. Accessories like vintage scarves were tied  around the neck, while caps, patterned ties, crossbody bags, and glasses tied many outfit together.

The Fall 2026 Milan Menswear street style showed how men layered outfits with different textures. From classic suits to casual combinations finished with detailed accessories.

See below for some of the best-dressed street style from the Fall 2026 Milan Menswear shows.

Photographed by Acielle / Style Du Monde

Photographed by Acielle / Style Du Monde

Photographed by Acielle / Style Du Monde

Photographed by Acielle / Style Du Monde

Photographed by Acielle / Style Du Monde