Here’s the thing: the best menswear inspo in 2025 isn’t on the runway or on Instagram. It’s hiding in plain sight—buried in old sitcoms, HBO classics, and teen dramas from an era before stylists and hype culture flattened personality into capsule wardrobes. Watch closely and you’ll realise that a lot of what’s trending today—relaxed tailoring, oversized shirts, no-fuss layers—already had a moment in the 90s and early 2000s.
So men, do yourselves a favour and stream these shows like your closet depends on it. Because it kind of does.
How 90s and Early 2000s TV Shows Are Shaping Today’s Menswear Trends
Seinfeld
The accidental blueprint for normcore
Jerry’s white sneakers, loose denim, tucked-in oxfords. Kramer’s wild button-ups and bowling shirts. George’s puffer vests and awkward layering. The characters dressed like real people, which is exactly why it works now. Think of it as accidental Aimé Leon Dore.
Friends
Men in oversized tees walked so The Row could run
The guys on Friends weren’t fashionable, but that’s what made their wardrobes so perfect. Relaxed fits, oversized crewnecks, corduroy trousers, and the kind of early millennial suiting that now feels like downtown luxury. Bonus points for Chandler’s sweater vest era and Joey’s flirtation with fashion risk.
The Sopranos
Mobster chic is the streetwear of the soul
Tony’s camp-collar shirts, Christopher’s leather jackets, Paulie’s tracksuits—it’s the East Coast Godfather of high-low style. Designers have turned this aesthetic into runway gold. At its core, it’s about looking like you mean business, even in a bowling shirt.
Sex and the City
Miranda Hobbes: menswear’s most underrated icon
Carrie got the column inches, but Miranda's wardrobe holds up better. Tailored trousers, crisp shirts, tonal suiting—it was the kind of grown-up style that's trending all over again. Swap the shoulder pads for cleaner cuts and you’re halfway to The Row’s lookbook.
Frasier
The rich sad man look, perfected
Frasier and Niles dressed like emotionally unavailable men with a New Yorker subscription. Camel coats, wool suits, rollnecks. It’s rich, brainy elegance, worn with the kind of insecurity that quietly says, “I collect art but have no one to share it with.” Which, apparently, is now a vibe.
Saved by the Bell
Preppy chaos, in the best way possible
Zack Morris’s colour-blocking, loud prints, and layers-on-layers feel like the more fun, less self-conscious version of current prep. If modern Ivy is polished and earnest, this was prep with a sugar high. Bonus: the return of baggy jeans and collegiate jackets owes a little something to this show.
Dawson’s Creek
Peak 90s minimalism before anyone knew what that was
Dawson, Pacey, and even Jack had that brooding, oversized flannel vibe down. This was off-duty preppy meets Pacific Northwest indie boy. Khakis, boat shoes, untucked shirts, and sad-boy knits that look suspiciously like a recent J.Crew drop.
The Fresh Prince of Bel-Air
Streetwear didn’t start on Hypebeast—it started here
Will Smith was doing colour theory, maximalism, and sneaker flexes before fashion cared. Reversible jackets, bold prints, Air Jordans, denim with attitude. It was streetwear before streetwear became a category. The new wave of retro-core owes everything to him.
Gossip Girl
Chuck Bass was your favourite fashion influencer’s favourite fashion influencer
Chuck didn’t care about your opinions—he had purple suits, paisley shirts, velvet slippers. While Dan leaned into Brooklyn indie basics, Chuck gave us old-money peacocking at its most theatrical. You wouldn’t wear it all, but you’d steal at least one thing from every fit.
Entourage
Slick tailoring for guys who think they’re chill
Vince played it safe, but Ari Gold? That man dressed like he was auditioning for power. Suits by Domenico Vacca, wide ties, big watches, and barely disguised aggression. Turtle brought sneaker culture, Drama brought gorpcore chaos, and together they nailed that slightly toxic LA masculinity we’re weirdly nostalgic for.
The Wire
Baltimore grit meets tactical layering
You weren’t watching The Wire for fashion—but it’s there. Omar’s trench coats and bulletproof vests. Stringer Bell’s quiet businessman fits. McNulty’s tired dad flannels and beat-up jeans. It’s unpolished, functional, and raw—basically what a lot of high-end menswear brands are chasing now under the guise of “realness.”
