Kendrick Lamar’s performance during the Apple Music Super Bowl LIX Halftime Show on February 9, 2025 in New Orleans, Louisiana, has sent waves through the fashion world. The rapper’s light blue Celine jeans, paired with a black T-shirt, blue letterman jacket, and shimmering diamond accessories, may seem effortless at first glance, but from a men’s fashion perspective, he has done something remarkable. Gliding across the stage as he delivered a powerful performance opposite Drake, Lamar has successfully revived the bootcut jeans trend with his flared denim.
Let’s be honest—everyone has had a love-hate relationship with bootcut jeans at some point. They’ve gone from cool to uncool and now they are back again. Whether you were a die-hard Hannah Montana or Britney Spears fan, or admired Saif Ali Khan’s street style, there’s no denying the power of the bootcut silhouette in elevating a simple outfit.
Katrina Kaif and Saif Ali Khan at the promotions of their film Phantom at PVR Juhu, Mumbai. (Express Photo by Dilip Kagda)
How did bootcut jeans get their name?
According to Manvi Goel, founder of Thnwhn, like many iconic fashion pieces, bootcut jeans started as a functional design before becoming a style statement. “Bootcut jeans got their name the old-fashioned way—by doing exactly what they were meant to do: fit over boots. Cowboys needed jeans that wouldn’t bunch up or strangle their footwear, so denim makers added a slight flare at the ankle,” she said. By the 70s, the disco era gave bootcuts a fresh identity—high-waisted, flared denim twirling under disco balls.
Anant Tanted, founder and CEO of The Indian Garage Co., said that bootcut jeans have existed for over 150 years. “The style traces back to sailor trousers from the 1850s, designed to fit over calf-high boots. That’s where the term ‘bootcut’ comes from—it was developed with boots in mind,” he told indianexpress.com.
According to him, bootcuts evolved from useful workwear to a fashion statement, gaining popularity in Hollywood Westerns, 70s hippie culture, 90s hip-hop, and even famous Y2K red carpet outfits. By the mid-1900s, bootcut jeans solidified their status as a cultural classic. Despite competition from bell-bottoms and flares in the 70s, bootcuts remained relevant through the 80s and early 2000s.
“Then came the Y2K era, when bootcut jeans became a wardrobe staple, worn by pop stars, rock bands, and suburban dads alike—thanks to brands like True Religion and Diesel,” said Goel.
Tanted said that in India, bootcuts really took off thanks to a wave of Western influence. Iconic stars like Zeenat Aman (in Dum Maaro Dum), Amitabh Bachchan in his famous movies in the 70s and 80s, and recently, stars like Yash and Ranveer Singh have made bootcuts a must-have.
Practical? Absolutely. Fashionable? Turns out, yes.
How can men style bootcut jeans?
Now that bootcut jeans have made a strong comeback, blending vintage appeal with modern versatility, styling them correctly is key to achieving a balanced, polished look for men.
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Stylist Rishi Raj said that there’s a difference between a classic bootcut and full bell-bottoms. “Opt for a slight flare to keep the look modern and wearable. Bootcut jeans should fit well at the thighs and taper slightly before the flare begins.” According to him, a baggy fit throughout can look outdated. He recommended avoiding loose shirts or boxy jackets that can overwhelm the silhouette and make the outfit look sloppy.
The trick to styling bootcut jeans is balance—think modern proportions with a vintage twist. “Take a cue from Kendrick Lamar and pair them with sneakers, an oversized tee, and a statement jacket for some edge. Want something better? Go for unique details in bootcut jeans instead of a regular pair,” said Goel.
Celebrity stylist Jhanvi Pallicha suggested opting for the right fit. “Stick to a length that skims the ground without pooling too much. Hem them if needed. Opt for neutral and darker washes since lighter washes can lean too retro if styled poorly,” she said.
Kendrick Lamar at Super Bowl. (Source: Instagram/@complexmusic)
Raj also said that the key is to wear shoes with some height or structure to maintain balance with the flare. According to Pallicha, boots such as Chelsea, cowboy, or combat are the most natural match for bootcut jeans. White sneakers or loafers can work for a more casual look.
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Pallicha also recommended layering smart. “Jackets like leather, bomber, or denim work well. Avoid overly long or oversized coats, which can overwhelm the look. Tuck in your shirt or try a half-tuck for a sharper silhouette,” she said.
Common styling mistakes to avoid:
- Going too baggy: Bootcut jeans are not the same as baggy jeans. Overly loose fits look outdated and sloppy.
- Ignoring proportion: Pairing bootcut jeans with oversized tops or coats can create a disproportionate silhouette.
- Avoid ultra-flat shoes and chunky sneakers at all costs.