Fashion’s a strange beast. One moment, you’re told that skinny jeans are dead; the next, baggy denim is back, and before you can even process that, a hip hop legend like Kendrick Lamar steps on stage at the Super Bowl and suddenly—against all odds—bootcut jeans are cool again. 

Yes, bootcut. The same jeans once exiled to the darkest corners of dad fashion. The same cut that, for the past decade, was reserved exclusively for country singers, Amitabh Bachchan movies and of course, Salman Khan sporing them no matter what the era.  

But then Kendrick, a known fashion minimalist, walked out in a pair of Celine bootcut jeans, and the internet had a full-scale field day. X (formerly known as Twitter) was ablaze with debates: Was this the second coming of Y2K fashion? Would we all be forced to start wearing cowboy boots? High-fashion critics, meanwhile, were calling it a moment—a signal that the fashion pendulum had swung yet again. 

Now, the real question: How do you wear bootcut jeans without looking like you time-travelled from the ‘70s? Let’s break it down. 

For years, men’s denim has been trapped in extremes: either so skinny you question your circulation or so wide you feel like a ‘90s skater kid. Bootcut jeans? They’re the middle ground. The beauty of them is in the silhouette. Snug at the thighs, subtly flared at the hem—just enough to cover a good pair of shoes. It’s a flattering cut, balancing out proportions while adding just the right amount of edge. 

And let’s be real: the fashion world is cyclical. Bell bottoms had their moment in the ‘70s, flared jeans ruled the early 2000s, and now, as Gen Z revives Y2K aesthetics, bootcut jeans are naturally having their resurgence. But this time around, they’re sharper, sleeker, and way more wearable. 

How to Style Bootcut Jeans Without Looking Like a Clown 

1. Footwear: The Make-or-Break Factor 

Boots (obviously): Chelsea boots, Cuban-heeled boots, even cowboy boots if you’re feeling bold—anything with a slight lift will balance out the flare and keep things looking intentional. 

Chunky sneakers: Think retro runners like New Balance 990s or Adidas Sambas. It’s a high-low mix that feels fresh, not forced. 

Loafers (if you dare): A polished leather loafer peeking out from under a bootcut hem? That’s confidence. Just make sure the jeans have the right break so they don’t swallow the shoe whole. 

2. What to Wear on Top 

T-shirts & Button-ups: A fitted crew-neck tee or a slightly relaxed button-up keeps things clean. 

Jackets: If you want to lean into the retro vibe, a bomber or leather jacket is your best bet. For a more modern approach, a cropped blazer or an oversized coat works wonders. 

Layering: A tucked-in tee with an open overshirt or lightweight knit adds depth without overwhelming the silhouette. 

3. Proportions Matter 

Length is Everything: Bootcut jeans should just graze the top of your shoe. No awkward bunching, no tripping over the hem. If you go too tight on top, it can veer into boyband territory. If you go too oversized, you risk drowning in fabric. The trick? A well-fitted tee or slim-to-regular-fit jacket keeps everything looking streamlined. 

Important Things To Note 

Spring/Summer: Light-wash denim with a boxy camp-collar shirt and sneakers for an effortless, slightly ‘70s Riviera vibe. 

Fall/Winter: Dark bootcut jeans, a chunky knit, and a tailored overcoat for a polished but relaxed cold-weather fit. 

Know Your Washes: Dark denim = sleeker, more polished. Light-wash = casual, vintage-inspired. Find the one that suits your style best.