Prada Fall 2025
Image Courtesy of Vogue Runway
January 27, 2025

Comfortably Classy is the Menswear Trend of Men’s Fashion Month

Men don’t want to look like expensive drifters anymore.

Gone one are the days of Hedi Slimane skin-tight skinny jeans and suction-cupped Chubbies shorts when it comes to the menswear trend landscape of 2025. Times are changing and so are the men—fashionable dudes all across the nation are swapping out their fitted, bodycon clothing for more seasonally appropriate cushy and comfortable silhouettes.

Now, this isn’t anything new. Weather gets colder, so clothes get warmer –that’s common sense. But, our trend reports have found that this particular fashion breeze we’ve been following into comfy clothes land has collided with another tried and true trend: “quiet luxury”. This has created a perfect sartorial tornado on the runway this season—one that we’re referring to as “comfortably classy”.

Men don’t want to look like expensive drifters anymore—sorry Demna Gvasalia. And Golden Goose. And PRPS. They want to look like high-end gentlemen—fellas laden with fine fabrics and quality knits, regardless of pattern or print.

Red Carpet Looks

We have already seen celebrities jumping onto the comfy classy trend. At the Nosferatu premiere in Berlin, Nicholas Hoult donned a particularly slouchy Dior Men’s suit with a silk shirt and cocoon jacket. Then Daniel Craig debuted a double-breasted pinstripe suit with sneakers and a white t-shirt for the Queer premiere. And for The Brutalist premiere, star Adrian Brody donned a particularly cozy oversized coat and matching set—in this almost boucle-style fabric. 

This trend is gaining traction in the sports world, too. Russell Westbrook walked into the area wearing a flannel-inspired blazer and a crisp pair of light-wash jeans. Karl Anthony Towns was spotted wearing a pair of tailored trousers and a puffer while getting out of his car. But James Johnson had the best outfits of them all: an orange plaid knit topped with a fleece jacket and beanie, the tallest Ugg boots you’ve ever seen and an “I heart my dog” tote—the perfect amount of refined and cool and casual.

Athlete Off-Duty

The variety here is really nice, because this leaves a lot of room for interpretation with the trend. You can make “comfortably classy” your own pretty easily, no matter your preferred sartorial genre. Looking for inspiration? Let’s head to the runway.

Men’s Fashion Week in Milan and Paris

John Alexander Skelton Fall 2025 showed looks for the old money eccentric: gingham trousers layered with corduroy coats and Count Orlok caps with verdant green trenches (buttoned to the top, no less).  

Prada Fall 2025 had a selection for all the Gen-Z, Spanish jamón heirs of the world: playful color palettes with wide-neck, cozy knits, fur vests beneath charcoal peacoats and elegant equestrian-inspired pullovers

The slick, sexy menswear fanatics should look no further than Egonlab for their fall dressing needs. The Egonlab FW25 collection featured sleek, barely-there knits, classy puppy dog prints and glam white fur coats atop black leather co-ords.  

Giorgio Armani brought out buttery soft cargo pants with green velvet cardigans this season—the perfect airport outfit if you ask me. Their collection also featured a type of knitwear that I thought would never come back into style: the papillon cardigan. Theirs is grey and ribbed knit and looks oh-so comfy. 

Now, let’s say you want something a little tougher. You’re not ready to get rid of the rugged, western cowboy look just yet. Well, fear not. Pharrell over at Louis Vuitton has you covered with polished work jackets and washed knit zip-ups to tell the world, “Hey, I’m tough—but I still like to snuggle up.”

Is the runway not enough? Maybe some Hollywood hunks in major motion pictures can get you into the comfy classy mood.

Film References

Talented Mr. Ripley is always the first place we send any wayward fashion bros. Matt Damon wearing loose-fit trousers, horse-bit loafers and a cashmere pullover on a Vespa? That’s class.

It’s also worth mentioning, the menswear in Knives Out is spot-on perfect. Chris Evans in an Irish fisherman’s sweater; Michael Shannon’s argyle sweater; all the perfectly worn-in suits. What’s there not to love?

We’ll leave you with one last perfect Fashion movie recommendation: Tom Ford’s A Single Man. Hoult’s fluffy, white mohair sweater? His beat-up corduroy work jacket? What about his little green checked button-up?

You know what? Just Google “Nicholas Hoult Red Carpet Fashion”. Copy any of those looks and you’ll be nailing the comfortably classy trend.

Kaitlin Owens

Kaitlin Owens is a Writer, Fashion Obsessive, Movie Buff and a Women's 7.5 (if any shoe brands are reading). She is a Vintage Fashion Columnist for Byline Magazine, the Archival Fashion Editor for Haloscope Magazine and the Editor in Chief of Dilettante. Kaitlin is from nowhere. She has lived in hotels and motels all around the world, but in 2020, she finally settled in the middle of Virginia with her husband and a big fat orange cat. She plans to spend the rest of her days buying taper candles at flea markets.

Accessibility Toolbar