Back in 2013, I sent out a tweet requesting images for my next knee-high boot article. My tweet was shared numerous times, but only one response came in from @StyleDivision—a definite no from me. There is a fine line between unique and ostentatious, and gentlemen, this winter, the knee-high boot is either a major trend or not a trend at all.
The question remains: can men confidently wear knee-high boots, or will they be judged into oblivion?
Who no other is trying than actor Pedro Pascal in 2025.
At London Collections: Men, I confronted David Gandy with this very question. J.W. Anderson’s catwalk had just paraded men in knee-high boots, and I wanted to know—how does such an audacious statement translate into an everyday wardrobe? The response? A mix of confusion, amusement, and a hefty dose of hesitation. The real issue isn’t whether knee-high boots can work for men; the issue is that most men don’t know how or where to wear them.
I took this inquiry to the most honest critic I could find—a six-year-old girl. Showing her an image of men in knee-high boots, she giggled and said, “They look funny, dressed up like girls.” Her reasoning? “Because men don’t wear dresses or boots like that.” And there it is—ingrained from a young age, society dictates what is and isn’t acceptable for men to wear. But should we let these outdated perceptions dictate our fashion choices?
The Art of the Knee-High Boot
A follower sent me a self-portrait of himself in knee-high boots, and I nearly fell off my chair in admiration. He nailed it—confidence, poise, and a bold rejection of societal norms. If you’re considering knee-high boots but lack the courage, take a page from his book. Own the look.
Massimo Dutti enlisted David Gandy to showcase an equestrian aesthetic, knee-high boots included. Yet, I remain skeptical that even Gandy himself can convince the average man to stride down the high street in them. After all, I have yet to see Mr. Gandy casually strolling about in knee-high boots. If he won’t do it, what hope is there for the rest?
My first article on knee-high boots was a hit, published over a year ago. Now, this is my third attempt to inspire men to embrace the trend. Whether mounted on a horse, riding a motorbike, or stepping out of a Jaguar, knee-high boots exude power and elegance. But where are the brave souls ready to champion this look?
For goodness’ sake, send me your images! Show me how you wear them. Or perhaps it’s time I stage my own photo shoot—to lead by example and finally inspire men to stride confidently in knee-high boots this winter.
Dare to be different. Or, at the very least, dare to be seen.
There’s A Fine Line Between Unique And Ostentatious
A crucial comment from a man regarding knee-high boots resonated deeply: there is a fine line between unique and ostentatious. But what do your boots say about you? Can you judge a man by his boots? Absolutely. This is precisely why no one dared to send me an image of themselves wearing knee-high boots. The fear of judgment looms large.
MenStyleFashion has always been about encouraging men to embrace style, to push beyond the expected. It’s not about right or wrong—it’s about defining yourself through fashion. Clothing is an extension of who you are, a visual proclamation of how daring you choose to be on any given day. Fashion isn’t about conforming; it’s about confidence. I don’t follow trends. I never have, and I never will. I simply don’t care what others think of my fashion sense because the true challenge isn’t about trends at all—it’s about stepping outside your comfort zone.
