The 7 Most Well-Dressed Sad Boys in Cinema
4 Min. ReadLet’s be honest. We don’t just cry for these characters, we crave their aesthetic. There’s something about a man unravelling in slow motion, drenched in Jacquemus, that hits differently. Maybe it’s the way their style seems to mirror their inner chaos. Maybe it’s the drama of it all. Either way, these aren’t your average emo boys. These are cinema’s best-dressed heartbreakers. Melancholy, but make it fashion.
1. Dev in Dev.D (2009)
Grit meets grunge in Anurag Kashyap’s reimagination of a doomed lover.
Dev isn’t tragic in the classical, brooding-by-the-window sense. He’s self-destructive, spiralling, and cocky. And he dresses like it. His look is a chaotic mix of leather jackets, dishevelled scarves, dark glasses at night, equal parts Delhi rich kid and fallen rockstar. His wardrobe doesn’t ask for sympathy. It says: I’m not okay, and I’m not pretending to be.
2. Paul in Aftersun (2022)
Sun-soaked sadness never looked so soft.
Paul Mescal’s character isn’t loud about his pain. It lingers in the silences, in the polaroid warmth of the film. His clothes follow suit: loose polos, baggy shorts, well-worn sneakers. Nothing fancy. But the quiet vulnerability in his dad-on-holiday fits somehow makes them devastating. He dresses like someone trying to hold it together, for his daughter, for the camera, for himself.
3. Jordan in Waves (2019)
A pastel tragedy in motion.
Before everything crashes, Kelvin Harrison Jr.’s Jordan is the picture of suburban cool. Tank tops, letterman jackets, sneakers too fresh to touch the ground. His style is polished, curated, and he’s a high school athlete with something to prove. But as the film peels him back, those same clothes start to feel like a costume. All swagger, no shield.
4. Ved in Tamasha (2015)
Corporate uniform by day, chaos-core by night.
Ranbir Kapoor’s character is quite literally split in two. As Ved, the product manager, he’s buttoned-up, tucked-in, painfully neat. But when he lets the storyteller out, everything loosens. Hair, collars, sanity. His best-dressed moment isn’t even a single outfit, it’s the transformation itself. Watching someone break free of their own costume is oddly beautiful, especially when it’s in slow motion, under yellow lights.
5. Elio in Call Me by Your Name (2017)
Peachy, preppy, and perpetually aching.
Timothée Chalamet’s Elio is a walking contradiction: young but ancient, naive but knowing. His summer-in-Italy wardrobe, flowy shirts, micro-shorts, and espadrilles oozes casual sensuality. But it’s also a form of camouflage. He’s trying to look breezy while carrying a love that’s breaking him open. By the end, the fits stay the same, but you see them differently. Softer. Sadder.
6. Janardhan/JJ in Rockstar (2011)
Style evolution is an emotional arc.
No one weaponises heartbreak quite like Ranbir Kapoor in Rockstar. His transformation from nerdy college boy to burnt-out musical icon is stitched into the clothes: kurtas layered over hoodies, Afghan-inspired jackets, worn-in boots. His look becomes heavier as the film progresses, both literally and metaphorically. It’s not just style. It’s armour.
7. Joel in Eternal Sunshine of the Spotless Mind (2004)
Muted tones, maximum existential crisis.
Joel’s wardrobe is like his personality: shy, slightly off, a little frayed around the edges. He lives in beanies, corduroy, and sad sweaters that look like they’ve been through multiple breakups. There’s no fashion statement here, just an accidental coherence that somehow works. His clothes aren’t trying to impress. They’re just trying to get through the day.
The Common Thread?
Each of these characters is falling apart. But never sloppily. Their style captures a specific kind of male melancholy, one that’s vulnerable, stylish, and quietly self-aware. These aren’t just sad boys. They’re aesthetic sad boys. And somehow, their heartbreak feels all the more tragic because they look so good while feeling so bad.
