When Stephen Libby stepped onto the set of The Traitors, he wasn't aiming to break the internet. But his chunky mint green knit and high-waisted denim did exactly that—sparking a flood of DMs from men desperate for style advice. The irony? He insists his look was nothing radical.
“Other than the jumpsuits, I don’t think I wore anything particularly groundbreaking,” Libby says. “The bar for men’s fashion is so low that a neutral outfit looks like a revelation.” For a generation raised on Y2K nostalgia and streetwear maximalism, his point hits hard: why are men still playing it safe?
From Isle of Lewis to Vintage Obsession
Libby’s style journey began in primary school on Scotland’s Isle of Lewis, where he first felt different. While other boys played it cool, he was turning up hems and studying the girls’ outfits. Fashion became his language—and his secret.
“I have vivid memories of a three-hour ferry and a 90-minute bus ride to Inverness just to shop,” he recalls. Topman visits felt sacred, but his first bold purchase—a grey-and-black striped cardigan—got him “ripped to shreds” at school. The lesson? Being ahead of the curve often means standing alone.
The Skinny Jean Rebellion
By 16, Libby was hiding his first pair of skinny jeans from his parents, changing into them only after leaving the house. “I wish I’d seen then that I was doing what straight guys would do years later,” he says. That secret rebellion laid the groundwork for a signature aesthetic.
University, Vintage, and Finding His Uniform
At Glasgow University, Libby lost his uniqueness—everyone had access to the same high street basics. So he turned to vintage, partly for budget reasons, but mostly for the drama. “The 60s, 70s, and 80s were a celebration of print and color,” he explains. “High street was all flat beige and white.”
His finds became armor: vintage Hawaiian shirts, flared trousers, and billowy sleeves. He even mourns a pale blue 70s suit he couldn’t afford at £50—proof that style investments stay with you.
The Look: Drama, Not Trends
Today, Libby’s uniform is unmistakable: dagger-collar shirts, high-waisted flares, and statement jewelry. Critics called him Simon Cowell early on, but he shrugs it off. “This is how I’m supposed to look.”
His advice for men? Start with vintage, embrace the flare, and don’t fear a little drama. The Y2K revival has made high-waisted and wide-leg silhouettes mainstream—so there’s no excuse for boring.
Why Men’s Fashion Is Stuck in Neutral
Libby’s Traitors experience exposed a deeper issue: men’s style lacks the experimentation women’s streetwear enjoys. While women cycle through micro-trends, men often cling to safe jeans and plain tees. The result? A low bar that makes any color feel revolutionary.
His solution is simple: borrow from women’s playbook. Try a fitted knit, a bold print, or a high-waist trouser. You don’t need a stylist—just curiosity.
Quick Style Upgrades for Men (That Work for Women Too)
- Swap straight-leg denim for a flared or wide-leg cut.
- Layer with a chunky knit in mint, lavender, or butter yellow.
- Add one vintage piece—a Hawaiian shirt or a 70s blazer.
- Accessorize with a pendant necklace or chunky ring.
- Invest in tailoring: high-waist pants that hit the ankle perfectly.
Comparison: High Street vs. Vintage for Streetwear
| Factor | High Street | Vintage |
|---|---|---|
| Price | Often cheaper upfront | Varies, but can be budget-friendly |
| Uniqueness | Mass-produced | One-of-a-kind finds |
| Fit | Standardized | Tailored or adjustable |
| Color/Print | Neutral-heavy | Bold, dramatic, eclectic |
| Sustainability | Fast fashion impact | Eco-friendly by default |
FAQ: Men’s Streetwear and Y2K Revival
1. Why is Y2K fashion so popular again?
Y2K’s mix of low-rise, high-waist, and techwear speaks to a generation nostalgic for early internet culture. It’s playful, bold, and gender-fluid—perfect for today’s streetwear.
2. How can men start wearing high-waisted jeans without looking dated?
Pair them with a fitted tee or crop top, and balance the volume with a slim silhouette on top. Add chunky sneakers or boots to modernize the look.
3. Is vintage shopping worth the effort?
Yes—vintage gives you unique pieces that no one else will have, often at lower prices. Plus, it’s more sustainable than buying new.
4. What’s the first item a man should buy to upgrade his wardrobe?
A chunky knit in a color like mint, lilac, or rust. It instantly adds personality and works with both jeans and trousers.
5. Can women wear these same tips?
Absolutely. Streetwear is fluid—flares, vintage shirts, and statement accessories are for everyone. The key is confidence.
Libby’s next columns promise tailoring, wedding dressing, and yes, jumpsuits. But for now, his message is clear: fashion isn’t about rules—it’s about showing up as your truest self. And if that means a mint green jumper and high-waisted jeans, so be it.
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