Bootcut Jeans Are Back! Here’s How to Wear Them Right Now

When Kendrick Lamar wore bootcut denim jeans during his halftime performance at Super Bowl 2025, Google searches surged as people (ourselves included), scrambled to figure out what style of jeans the rapper was wearing.

And for the uninitiated, the Grammy-winning rapper opted for Celine’s light-washed Flared Surf Jeans in Summer Wash during his highly praised musical performance. He paired the vintage-inspired jeans with a custom Martine Rose leather bomber jacket featuring the word ‘Gloria’ across the front, a reference to the track on his latest GNX album.

Bootcut jeans are a timeless wardrobe piece that never truly goes out of style. Even as trends change, they remain a reliable option. Today's bootcut jeans feature modern updates, including high and medium-rise waistlines, a variety of washes and colours, and designs that elongate the legs. These contemporary touches add a fresh twist to a classic silhouette, making them a popular option for many.

Over the past decade, style icons like Bella Hadid, Gigi Hadid, Victoria Beckham, Emily Ratajkowski, and Kate Moss, among others, have embraced the bootcut jean look, contributing to its resurgence as one of fashion's many comebacks.

Bootcut vs Flare: The difference

Bootcut jeans were a defining trend of the 2000s — low-rise, distressed, and typically worn with crop tops and chunky belts. While they aren’t a new style, denim trends have a way of revisiting the spotlight. Designed for daily wear, these jeans are the relaxed, cooler counterpart to skinny jeans – also enjoying a resurgence. Additionally, they are often confused with flare jeans, thanks to their similar cuts and wide flares. However, there is a difference between the two — let’s break it down.

Bootcut and flared jeans may appear similar but they are quite different in design. Both are snug through the thighs, but the key difference lies in how and where they flare out. Flared jeans feature a sharp, pronounced widening starting from the knee, and in contrast, bootcut jeans have a more gradual flare that begins at the knee and opens up subtly from the mid-calf down, giving a softer and refined shape.

Styling bootcut denims

Denim on denim

When someone mentions denim on denim, it often brings to mind Britney Spears and Justin Timberlake's iconic take on the trend in the early 2000s. With this inspiration, you can style your bootcut jeans with either a fitted or slightly oversized denim jacket. The contrast between the slim upper body and flared lower body creates a balanced silhouette. For a modern twist, consider a slightly cropped jacket, or opt for a classic longer style for a more relaxed vibe.

Another way to master the denim-on-denim trend is by pairing a light-wash denim jacket with dark-wash bootcut jeans for a striking contrast. Alternatively, you can create a signature monochrome look by choosing a matching light or dark denim combination.

Business casual

If you wish to add oomph to your business casual look, opt for tailored pieces that will maintain a professional vibe with a polished aesthetic. A timeless approach would be to style bootcut denim with an oversized button-down, exuding understated elegance. For a more structured aesthetic, pair your bootcut jeans with a sharply tailored blazer in a refined palette of navy, black, or beige. The contrast between the structured blazer and relaxed denim creates a stylish yet effortless outfit.

Turtlenecks FTW!

For an off-duty model look, bootcut jeans and turtlenecks are your go-to. Pair your jeans with a fitted or semi-fitted turtleneck top or sweater for a sleek Kendall Jenner-esque look. It looks best when you opt for neutrals like black, beige, or white, or add a pop of luxury with deep burgundy or forest green. The motto? Simple, sleek, and always in style.

Sporty wear

If you want to channel your inner Bella Hadid, pair your bootcut jeans with athletic jackets or oversized hoodies. Throw on an athletic jacket—like a bomber, track jacket, or windbreaker—over a hoodie or tee. Finish with trendy sneakers like Nike Jordans or ASICS trainers for a cool, everyday look.

TSL’s bootcut denim jeans picks!

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