Just before 1.00pm on 18 February 2011, a customer in New York logged onto his computer, typed in mrporter.com and made a purchase, the first in our history. It was for a Turnbull & Asser tie, a John Smedley sweater and a pair of Incotex chinos. Fifteen years and countless milestones later, that’s still a great order. And while the style landscape looks markedly different now compared to those early days, men are still into quality trousers and British cashmere. Even ties have made a comeback.

As CEO Toby Bateman said soon after launching: “We quickly saw that our customer base encompassed everyone from 18-year-olds using their first bit of money to buy a sneaker, and 80-year-olds shopping shirts and ties.”

To celebrate our 15th birthday, we spoke with a handful of successful and stylish guys to compile a bit of a state of the union. We wanted to find out their thoughts and feelings on where menswear’s been and where it’s headed.

“It was a great time,” says the author, curator and model Jason Jules. “Because it was still in its infancy, there was a lot of discovery and new relationships developing. The brands that had been the real foundation of authentic menswear were getting recognition by a wider, younger and more enthusiastic customer and then there were all these new brands emerging in that period, too.”

“The big trend from 2011 was the ultra-slim silhouette,” says the designer Oliver Spencer, whose namesake brand has been with MR PORTER since the very start. “Short, skinny jackets, slim-cut tailored trousers, denim that followed suit and very fitted shirting where specific sizing mattered a lot. It’s the silhouette we wear now – boxy fits, wide legs, relaxed shirting – that makes those 2011 pieces feel so dated when you pull them from the archive.

“Menswear silhouettes change slowly, so the shift wasn’t obvious until you looked back over a decade,” says Spencer.

“It was just before the streetwear revolution, which really only kicked in around 2015,” adds Nick Sullivan, the creative director of Esquire US. “In 2011, tailored clothing was still the bedrock of grown-up luxury. There had been a kind of dandy revolution in men’s fashion that was all tricked out in pocket squares and belted coats and, if you could get away with it, a fedora. There were less ties, but you still wore shoes rather than sneakers to work.

“You were either a casual guy or a dressy guy, and it was often defined by where you worked. Now we’re all one and the same. In some ways I miss it.”

“I moved from California to New York in 2011, and I remember telling myself to forget everything I ever thought I knew about style,” says Tyler Watamanuk, a writer and the author of Bigger Than Fashion: How Streetwear Conquered Culture. “You could walk a half block and see five different well-styled guys dressed five different ways. It now feels like a moment in time; it felt like the last breath of the 2000s ‘metrosexual’, which took its final form in Ryan Gosling’s character in Crazy, Stupid, Love.”

Ryan Gosling is a name that comes up a lot when talking about men’s style of 2011, and especially his turn in that year’s romantic comedy, Crazy, Stupid, Love. That look – a tight suit with slim cropped trousers, smart shoes (bonus points if they featured a monk strap) in a shade of brown on the chicken korma Pantone scale – was everywhere back then. Some guys even tried, and inevitably failed, to pull off the Drive scorpion bomber jacket.

Menswear felt pristine and slim fitting. Narrow chinos, box-fresh Common Projects and crisp Oxford shirts. Or skinny jeans, flannel shirts and Chelsea boots… A lot of Chelsea boots. Capsule wardrobes were a real obsession, and men were beginning to talk about clothes seriously on the internet. #Menswear gained traction with the launch of Instagram, and there were heated forum debates about selvedge denim and desert boots. “Proportions were all over the place,” says the photographer Chris Fenimore, who has spent years photographing men’s style in the wild.

“These silhouettes are cyclical,” he adds, “so I suspect people will be back wearing overly slim stuff soon. There is only so much you can do to make clothing or fashion new, and usually if something is truly unique and fresh, it’s going to look dated in the near future.”

“Looking back, the insanely neat pin-rolled jeans and chinos, and the sheer amount of ankle men were showing during that 2011 era, feel very much like a moment in time to me,” Watamanuk says. “Rappers were then starting to dress insanely fashion-forward. Skinny jeans went fully mainstream. Rick Owens and Raf Simons were on their way to being part of a certain millennial vernacular. It felt like all this stuff was put into a pressure cooker – and then it just exploded throughout the rest of the 2010s thanks to social media and celebrities.”

All of which led to the mid-2010s streetwear boom, when figures like Kanye West, Pharrell Williams, Virgil Abloh, Demna and Tyler, the Creator became cultural juggernauts. When European houses with centuries of heritage went all-in on logos and a more youthful take on luxury. People spent a lot of money on sneakers, while men’s fashion fully entered the mainstream.

“Men are way more enthusiastic than they were.” Sullivan says. “And many are better informed and, as a result, better dressed. Chiefly, I’d say men are better at layering. But many are also often ill-informed, leading them to make regrettable short-term fashion choices. There’s just way more information out there. Not all of it is good. Where you get your information is critical.”

“The world might be going to hell in a handbasket, but I’m bullish on menswear,” the menswear writer Eric Twardzik says. “I find myself fielding questions from friends who are looking for a safari jacket, investing in Goodyear-welted boots or having their first bespoke suit made. I think men are much more comfortable and confident in expressing themselves through clothing, and that’s a sea change from when I was growing up.”

After minimalism, workwear and the streetwear years, it feels like menswear has both settled and diffused. There’s room for everyone. You can dress in full Rick Owens mesh and leather, oatmeal hues of Brunello Cucinelli cashmere, garment-dyed Stone Island or as a RRL fancy cowboy. Quiet luxury had a moment, and running style has never been bigger. One theory is that it scratches that streetwear itch, with its focus on logos and technical fabrics… Although you do have to post your 10k time on Strava.

We’re also in the midst of a prep resurgence, as shown by the clubhouse popularity of the likes of Drake’s, Aimé Leon Dore and the evergreen Polo Ralph Lauren, combining heritage, vintage and flashes of colour. And, as Sullivan said, we have gotten better at layering.

“When we think of 2026 down the line, I think it will be the relaxed silhouettes and the wide-leg trousers that will stand out,” Spencer says.

“Ralph Lauren’s Rugby label feels particularly reminiscent of 2011, or that general period, but in a good way,” Jules says. “It was the best of what menswear was about at that time – preppy-inspired, vintage-based, playful, affordable and well made. I think personal brands like Aaron Levine will define this period more than corporate brands. People’s taste and how they navigate around all the choices we have will matter more and more.”

“There’s a natural progression,” Twardzik says. “The young man chases after loud colours, busy patterns and flashy details like slanted pockets and bi-swing backs. As one gets older, you pay more attention to fabric quality and fit, and things get a little more sober and cohesive. I feel like I’ve had that whole journey myself, where I’m getting back to being a little louder and bolder as I better understand the rules and feel much more confident with my choices.”

Over the past decade and a half, MR PORTER has gone from stocking 80 brands to more than 320. There have been exclusive collaborations, including the time we designed a BMW i3, the launch of our own label, Mr P., luxury watches, the costume-to-collection Kingsman line, our Health In Mind charity and an ongoing commitment to working with the best designers and brands, stocking clothes that men from all over the world want to wear.

Fun fact: the most remote order in our history came from the Cook Islands, approximately 10,000 miles from our London headquarters.

As Jules surmises when asked about whether we should feel optimistic about the present and future of men’s style: “Values like authenticity, self-expression, individuality and mutual respect, which underpinned the menswear boom back then, are just as valid, if not more important today, I think.”