I'm Envious of Men's Clothes These Days: 'Whimsy Maxxing' Set to Captivate 2026!
'Whimsy Maxxing'—have you heard that word? 'Whimsy' originally means a quirky, lovable imagination or playful detail. Added to it is the internet-style expression 'maxxing,' meaning to maximize something, and together it refers to a style that freely showcases the fun of dressing. Is it a revolt against the long-running trend of 'quiet luxury'? Savannah Scott, creative director at strategic foresight agency The Future Laboratory, describes it as 'a shift where joy itself becomes a new symbol of status.'
This mood is spreading quickly into menswear, too. Menswear journalist Nick Carvell told Vogue, 'Whimsy Maxxing feels like a new way for people who are secure in their masculinity to express themselves.' Mixing clashing prints or wearing brooches, for example. He described it as 'a trend that adds nostalgic sensibility and playful color and patterns to menswear that feels crafted,' calling it 'the most fun menswear moment since I entered the fashion industry.'
Stylishly dressed celebrities have already mastered whimsymassing. Harry Styles has worn a sparkling leopard-print jacket, Jacob Elordi has worn Dior ballet flats. Actor Connor Swindells has worn a Tiffany & Co. diamond cocktail watch.
Even if you're not into the so-called 'boyfriend look' style you see online, Whimsy Maxxing offers elements anyone can reference. Let's look at why this trend has emerged and how to use it in everyday life.
Why Has Menswear Become More 'Whimsy' Now?
There are a few reasons this playful, bold aesthetic has spread. The biggest is timing. After several years of neutral-toned cashmere, neat shirts, and beige-centered minimalism, the tide has started to turn the other way—toward color and personality.
Fashion writer Lauren Cochrane explains, 'There’s definitely a backlash against quiet luxury right now.' 'There’s a bit of a “screw it” vibe too. Of course men have long worn flamboyant clothes—just look at Mick Jagger and Jimi Hendrix. I think Harry Styles, Dior, and Dries Van Noten also sit on that mood board. What’s different now is that that style is being accepted much more naturally in everyday life.'
Mick Jagger performing, 1994.
Jimi Hendrix performing, 1969.
This shift is visible off the red carpet too. Nick Carvell says, 'You especially see it when men dress up to go out.' Adding colorful jewelry at an evening event, or casually showing a silk scarf under a baseball cap on the weekend. It’s not limited to nightlife. He recently saw a man in Chelsea wearing a grey suit and pink shirt with boldly patterned socks. It looked very office-worker, but the socks made it feel like 'office whimsy maxxing.'
'Online there’s still a very coercive atmosphere trying to define masculinity—what people call the “manosphere.” Whimsy Maxxing feels like a visual counterreaction to that.' Ultimately, this links to a larger cultural shift. Savannah Scott says we’re moving away from a self-optimization-centered 'maxxing' culture—the obsession with appearance called 'looksmaxxing,' the fixation on scent called 'smellmaxxing,' health optimization 'healthmaxxing,' and even attempts to improve personality called 'personalitymaxxing.' Instead, she explains, 'joy and softness, and a pinch of elegant absurdity' are becoming more important. Attention is shifting from looking perfect to looking joyful.
How Do You Start a Whimsy Maxxing Style?
Celebrity stylist Itunu Oke says it depends on 'how daring you want to be.' 'Most men start with accessories. It’s the least daunting entry point.' Brooches, jewelry, colorful bags, distinctive watches, bright pocket squares. These are elements that repeatedly appeared in Hermès and Etro collections for the 2026 spring/summer season. The key is adding 'fun details' that change the mood of a look.
Hermès 2026 S/S Menswear
Fashion writer and presenter Dino Bonačić offers similar advice. He’s someone who has enjoyed 'whimsy' style for a long time. 'If you’re drawn to whimsical style, start small. Ultimately, small details are what create the mood.'
For example, a thin gold bracelet watch reminiscent of Tyler, The Creator, or a distinctive vintage watch. He recommends hunting for these items secondhand on sites like Vinted or eBay. Shoes are also a great entry item. 'Ballet shoes will be an excellent compromise between tradition, whimsy, and practicality. And nowadays there are options even up to basketball-player sizes, so choices are varied.'
What matters in the end is an attitude of enjoyment. Content creator Saad Akhtar abandoned the uniform style typical of finance workers and went viral with his own whimsy style. He often wears small T-shirts, cherry wood loafers that look like they came from a grandfather’s wardrobe, and small, thin vintage Gucci watches that feel like women's pieces. Watching a few minutes of his videos makes it easy to understand why people are drawn to this style.
Which Brands Do Whimsy Maxxing Best?
Some designers embed a whimsical mood into the clothes themselves. Mithridate, led by designer Daniel W. Fletcher, is a prime example. It adds unexpected details to classic menswear—button-down shirts with pink scarves edged in fringe, or cardigans hand-embroidered with puppy motifs.
Fletcher explains, 'You get much more interesting results when you mix atypical inspirations into classic menswear.' He says that in school he drew a lot of inspiration from 1960s Vogue magazines and historic portraiture. 'It’s about reinterpreting small but interesting moments in a contemporary way.' But the important thing is balance so it doesn't look like a costume. Fletcher also emphasizes, 'At the end of the day, these are clothes people actually wear.'
Charles Minton wearing a custom piece by Mithridate.
Dries Van Noten has long offered romantic menswear with flowing silhouettes and luxurious fabrics, and Bode is loved for a vintage American sensibility that feels found in an eccentric uncle’s attic. Simone Rocha has consistently brought details like frills, ribbons, pearls, sequins, and floral embellishments into menswear as well.
Dries Van Noten 2026 F/W RTW
Simone Rocha 2026 S/S Menswear
Bode 2026 F/W RTW
Whether you wear a blouse with a ribbon, go to the office in ballet flats, or start with bold colored socks, it doesn’t matter. Add a little 'whimsy' to your everyday life.
Published: May 15, 2026
