By Rifan Muazin 
The resurgence of the bootcut is not merely a nostalgic nod to the 1970s or the early 2000s; it is a pragmatic response to the evolving geometry of the modern male frame. My personal menswear crystal ball does not show the roomier jean trend swinging back toward anything slimmer than a straight-leg anytime soon. Major industry bellwethers like Levi’s are only just beginning to lean into their new, looser designs, signaling a long-term market shift away from the restrictive fits of the 2010s. This shift only strengthens my conviction that every man today should integrate a bootcut jean into his rotation. It offers a unique combination of relaxed ease and sophisticated lines that straight-leg jeans often fail to capture.
The brilliance of the bootcut lies in its architectural balance. A bootcut jean possesses the generous leg opening of a wider jean, providing the same versatility with footwear—whether it be a heeled Chelsea boot, a relaxed loafer, a sturdy black Derby, or a classic sneaker. However, unlike the baggy fits that can sometimes swallow a person’s frame, the bootcut remains slimmer through the seat and thigh. This "V-shape" in reverse creates a more sophisticated profile, particularly when the denim is paired with structured upper-body pieces like a tailored blazer, a high-quality knit, or a rugged leather jacket for an evening out.
For many of the "regular guys" I work with, the initial resistance to the bootcut stems from a fear of "cowboy cosplay." There is a lingering misconception that wearing a bootcut requires a ten-gallon hat and a silver belt buckle. My goal in recommending these pants is never to encourage a costume; rather, it is to introduce versatility and visual interest into a denim rotation that has likely become stagnant. A bootcut provides a new set of lines for the eye to follow. It has a magical ability to pair just as effectively with cropped outerwear—such as Harrington jackets or denim truckers—as it does with long, flowing silhouettes like overcoats and trenches. It creates an elongated leg line that is universally flattering, making the wearer appear taller and more grounded.
Understanding why this silhouette works requires looking at the history of the fit. The bootcut was born out of necessity, originally designed for 19th-century sailors who needed "bell-bottoms" that could be easily rolled up or removed over boots. By the time Levi Strauss & Co. introduced the 517 Boot Cut in 1969, the style had been refined for the American West, designed specifically to fit over high-top riding boots while maintaining a slim, functional fit through the leg. This history of utility is what gives the bootcut its "honest" feel. It is a workwear staple that was co-opted by fashion, not a trend manufactured in a boardroom.
In my own wardrobe, I have become particularly fond of vintage Levi’s 517s. There is a specific joy in the hunt for the perfect pair—the way the denim has aged over decades, the unique fades that can only be earned through years of wear, and the rigid feel of old-school cotton. However, I recognize that not every man has the time or the inclination to scour vintage shops or online marketplaces for the perfect 1980s "orange tab" find. Fortunately, the current market has caught up to the demand, and several brands are now producing off-the-rack options that capture the essence of the classic bootcut while updating the fabric and finish for modern sensibilities.
The "Bootcut Jeans Hit List" represents the pinnacle of what is currently available, ranging from heritage classics to contemporary interpretations.
Leading the pack is "The Timeless Pick": the Levi’s 517 Bootcut Jeans. Priced at a highly accessible $98, these are the gold standard. They are the blueprint from which all other bootcuts are derived. The 517 is designed to sit at the waist, with a slim fit through the thigh and a gradual flare from the knee down. For the man who wants the authentic experience without the vintage price tag, these are unbeatable. They provide that rugged, Americana aesthetic that looks just as good with a white t-shirt as it does with a dress shirt.
For those looking for something a bit more refined, "The Dressier Pick" comes from Frame. At $268, these jeans represent a move into the luxury denim space. Frame has mastered the art of the "elevated" bootcut, using premium denim that holds its shape while offering a softer hand-feel. These are the jeans you wear when you want the comfort of denim but the silhouette of a trouser. They are streamlined, often coming in darker, more uniform washes that make them appropriate for a business-casual office or a high-end dinner.
"The Looser Pick" is offered by COS, the London-based purveyor of minimalist style. Their Relaxed-Fit Bootcut Jeans, priced at $139, are a brilliant hybrid. They take the DNA of the bootcut and merge it with the current trend for wider, more architectural leg shapes. This pair is for the man who wants to experiment with volume but still wants the intentionality of a flared hem. They look particularly striking when paired with modern, minimalist sneakers or chunky lug-sole boots.
J.Crew offers "The Washed Out Pick" with their Bootcut Jean in Rinsed Wash, currently retailing for approximately $150 to $188 depending on sales. J.Crew has spent the last few years revitalizing its denim program, and this pair is a testament to that effort. The "creased indigo" or "rinsed" look gives the jeans a pre-broken-in feel, capturing that elusive vintage aesthetic without the search. They are the perfect "weekend" jeans—reliable, comfortable, and stylistically versatile.
Finally, for those seeking the best value, "The Bang-For-Your-Buck Pick" is Madewell’s The Bootcut Jeans. Priced at $148, Madewell has utilized its reputation for excellent fit and durable construction to create a bootcut that feels substantial. They offer a slightly more modern take on the flare, ensuring it is noticeable but not dramatic, making it an ideal "entry-point" pair for someone nervous about moving away from straight-leg styles.
Beyond the specific brands, the key to pulling off the bootcut is understanding the "break"—the point where the hem of the pant meets the shoe. In my newsletter, Where Your Pants Break, I often discuss how the relationship between the trouser cuff and the footwear can define an entire outfit. With bootcut jeans, you generally want a slight break or a "full break." Because the leg opening is wider, the fabric should drape over the shoe, covering a significant portion of the laces or the shaft of a boot. This creates a seamless vertical line that elongates the leg. If the jeans are too short, the flare can look unintentional; if they are too long, they will drag and fray. Finding that "Goldilocks" length is the secret to making the bootcut look intentional and polished.
The anthropology of getting dressed is about more than just following trends; it is about finding pieces that endure because they function well in real life. The bootcut has endured because it solves a problem: it balances the proportions of the male body better than almost any other cut. It accommodates the muscularity of the thighs while providing enough room at the ankle to prevent the "ice cream cone" effect often seen with tapered jeans.
As we move further into a decade defined by a return to classicism and a rejection of the "ultra-slim" era, the bootcut stands as a beacon of style for the regular guy. It is a silhouette that respects the past while feeling entirely relevant to the present. Whether you are opting for the heritage of Levi’s or the modernism of COS, the message remains the same: give your straight-legs a rest and embrace the flare. It is the easiest way to inject a bit of personal flair into your wardrobe without sacrificing the comfort and reliability that denim is supposed to provide. In the end, getting dudes into pants that actually fit is about more than measurements—it’s about confidence, and nothing provides a confident stance quite like a well-fitted pair of bootcut jeans.