By Rifan Muazin 
As we transition through the late summer heat and look toward the structured layers of autumn, the industry’s most entertaining men are offering a masterclass in versatility. Whether you are looking to experiment with a "freaky" chartreuse top, deciding if this is finally the year to invest in a pinstriped power suit, or succumbing to the masculine urge to buy your first pair of authentic cowboy boots, consider this your definitive cue card for the season.
The Herringbone Heartthrob: Drew Starkey
Drew Starkey, the breakout star of Outer Banks who is currently generating significant awards-season buzz for his role in Luca Guadagnino’s Queer, has been on a press run characterized by high-fashion pivots. Moving effortlessly between the structured elegance of Dior, the avant-garde prints of Dries Van Noten, and the classic Americana of Ralph Lauren, Starkey has found a sweet spot in "textured minimalism."
In a recent appearance, Starkey channeled a young Ethan Hawke, pairing a classic herringbone blazer with a simple striped long-sleeve tee. This look is a prime example of successful pattern clashing. The key lies in the scale: the fine, busy texture of the J.Mueser Waverly herringbone blazer provides a sophisticated backdrop for the broader, more graphic lines of the Save Khaki organic hemp stripe crew tee. By keeping the bottom half of the outfit subtle—likely a pair of dark chinos or well-fitted denim—he allows the interplay of textures on the upper body to command attention. This is a "stealable" look because it elevates the standard t-shirt-and-blazer combo from "business casual" to "art-house cool."
The Perennial Pinstripes: Jacob Elordi
Pinstripes are notoriously difficult to pull off without looking like a 1920s caricature or a mid-level investment banker, but Jacob Elordi makes the look seem effortless. Standing at a commanding 6’5", the Euphoria and Priscilla star does not necessarily need help elongating his frame, yet the verticality of the pinstripe suit only adds to his "Old Hollywood" leading-man aura.
Elordi’s look—centered around a midnight navy wool suit from the Parisian brand Husbands—is all about the details. He bypasses the traditional silk tie in favor of a black knit tie from J.Press, a choice that adds a tactile, modern edge to the formal silhouette. Furthermore, his choice of a "full break" in the trousers signals a shift in menswear trends. While the last decade was dominated by the super-slim, "no-break" look that hit just above the ankle, Elordi’s choice to let the fabric pool slightly over his Church’s leather derby shoes suggests a return to a more mature, relaxed tailoring. Finished with Oliver Peoples sunglasses, the outfit is a masterclass in "Star Power" dressing.
Tour de Force in Menswear: Harry Styles
As Harry Styles geared up for his legendary 30-night residency at Madison Square Garden, his "off-duty" arrivals in New York City became just as anticipated as his stage costumes. Styles has been instrumental in the "soft-boy" fashion movement, blending gender-fluid elements with vintage silhouettes.
His latest snapshot is perhaps his most attainable fit yet. It centers on a flowy, oversized white dress shirt from Studio Nicholson—the kind of piece that suggests he didn’t give a single damn while getting dressed, yet looks perfectly draped. He paired this with high-waisted, pleated wool trousers from Mfpen and "soft-boy" shoes (Prada shuffle antiqued leather laced shoes). The inclusion of a thrashed baseball cap (an "Idea Now" techno-themed hat) serves as the ultimate high-low stabilizer. This look is a future mood-board staple; it is the blueprint for how men will likely be dressing in 2046: comfortable, slightly feminine, yet undeniably masculine in its confidence.
Real Ranch Dressing: Glen Powell
Glen Powell is living proof of the adage that you can take the man out of Texas, but you cannot take Texas out of the man. Following the massive success of Top Gun: Maverick and Twisters, Powell has fully embraced "Western-wear-pilled" aesthetics. His style reflects a broader cultural resurgence of "Cowboy Core," fueled by both cinematic trends and a return to rugged Americana.
Powell’s outfit is a balanced mix of "gym-ready" and "ranch-ready." A tight white tank top highlights his physique—the result of rigorous training—while an open Gardner knitted zip cardigan from Percival adds a layer of sophisticated softness. The anchor of the look, however, is the authentic Western hardware: a McCoy II bison leather belt and Tecovas cowboy boots. Even his rescue dog, Brisket, serves as the ultimate accessory for this modern frontiersman look. It’s a style that works because it doesn’t feel like a costume; it feels like a homecoming.
The Methodical Monochromatic Kit: Jonathan Daviss
Since the announcement that he will portray the legendary Snoop Dogg in an upcoming biopic, Outer Banks star Jonathan Daviss has begun to adopt a "Doggfather-esque" swagger. Letting his hair grow out to recreate the signature look of the West Coast icon, Daviss has leaned into the power of the monochromatic silhouette.
An all-black outfit is often seen as a safe choice, but Daviss proves it can be a bold one when the fit is immaculate. By pairing a J.Crew cashmere crewneck sweater with Todd Snyder Italian gabardine Gurkha trousers, he creates a sleek, uninterrupted line that emphasizes his height and build. The addition of black Chelsea boots and "badass" shades creates an air of mystery and authority. Monochromatic dressing is a psychological tool; it projects a sense of being "put together" without the need for loud logos or clashing colors.
A Touch of Added Texture: Josh Brolin
Josh Brolin’s style has evolved into something uniquely rugged and refined, described by fashion critics as being "dressed up like a hand-rolled cigar." Brolin excels at utilizing an autumnal palette of tobacco, sienna, and deep browns.
At a recent event, Brolin showcased the importance of material contrast. His relaxed-fit suit jacket from Vowels and striped shirt from Jeanerica provided a solid base, but the choice of footwear was the "next-level" move. While a standard leather boot would have blended into the suit, his choice of Morjas suede Chelsea boots added a necessary layer of texture. Suede absorbs light differently than leather, providing a matte finish that makes the outfit feel "moody" and lived-in rather than corporate. It is a look for the man who wants to appear sophisticated but still looks like he could handle himself in a bar fight.
Char-Stachio Drip: Jack Innanen
Jack Innanen, the viral sketch-comedy star and breakout actor in Adults, is a pioneer of the "gender-neutral" shopping trend. His first tip for being one of the flyest guys around? Don’t be afraid to cross the aisle into the women’s section.
Innanen’s recent look featured a chartreuse (or "char-stachio") top from the cult women’s brand 6397, paired with wide-leg jeans from the same label. The standout element of the outfit, however, was a "ludicrously capacious" Balenciaga Rodeo handbag. The oversized tote bag trend has exploded in menswear, moving away from the small cross-body bags of previous years toward massive, statement-making carriers. The chartreuse color is a "high-risk, high-reward" choice that works perfectly when grounded by neutral denim and confident accessories.
The Slim Fit Silhouette: A$AP Rocky
While the fashion world has spent the last five years obsessed with oversized "baggy" fits, A$AP Rocky—the perpetual early adopter—is already signaling a return to the slim-fit silhouette. Not waiting for the runways of 2026 to give him permission, Rocky has been spotted on "dad duty" in Harlem wearing slim-fitting Loro Piana cotton-twill trousers.
The silhouette here is all about architectural balance. Rocky pairs the slim bottoms with a boxier, slightly cropped Ralph Lauren Purple Label tee to ensure the look doesn’t appear too "skinny" or dated. He finishes the ensemble with suede Venetian loafers from Meermin and a New York Yankees snapback. This "hometown hero" accessory makes an otherwise incredibly expensive, luxe-as-f**k outfit feel approachable and grounded. Rocky reminds us that the best outfits aren’t just about the clothes; they are about how you balance the proportions to fit your own personal narrative.
In conclusion, August’s celebrity style landscape suggests that the "rules" of menswear are increasingly fluid. Whether it is the Western ruggedness of Glen Powell, the gender-bending minimalism of Harry Styles, or the calculated tailoring of Jacob Elordi, the overarching theme is intentionality. Stealing these looks isn’t about copying the brand names; it’s about adopting the logic behind the layers, the textures, and the silhouettes that define modern masculinity.
