June is a time for vacation, or holiday as the Europeans call it: dash away to your nearest, cleanest body of water, lushest tropical locale, or costliest villa somewhere your friends can envy via Instagram. In fashion, the calendar’s midway point is a time for designers to explore concepts fit for summer, designing for next year’s warm weather trends while reflecting on the style changes that high temperatures bring about.

This Spring/Summer 2025 season, menswear and women’s Resort collections shared a spirit of dumping city bustle for a more relaxing holiday, whether in Adrian Appiolaza’s escape-from-the-city paradise for Moschino or JW Anderson’s pillowy dreamscape. A transcendental throughline also echoed through Milan’s shows, from Zegna’s environmentally conscious Oasi linens to Emporio Armani’s fictional lavender-tinged beaches. There is life beyond the nine-to-five office culture, these collections insist—perhaps sunbathing in Prada wraparound sunglasses or ditching the power suit for a bondage harness, as suggested by DSquared2.

Nevertheless, the men’s and resort seasons show designers and their teams have been hard at work. May the international fashion crown find respite in the breezy fantasies Milan offered. In this round-up, Document collected the most OOO-email-inspiring collections from men’s Spring/Summer and women’s Resort week in Milan.

Prada
The Prada universe was felt in full force for its men’s Spring/Summer 2025 runway, with the label’s signature fully felt down to the pant hems and even the models’ haircuts. Titled Closer, co-creative directors Raf Simons and Miuccia Prada were inspired by the myriad questions that surround perception: Is there a such thing as a universal truth based on what we can see, or should we “question the actuality of what we perceive, to reconsider, to look at things closer?” as asked by a press release. This season’s eyewear represented this inquiry literally. Mirrored wraparound sunglasses were printed with outdoor landscapes of beaches, lakehouse horizons, and crowds, causing the lenses that permanently mimic the feeling of looking at a live event through the reflection of a stranger’s sunglass lenses. These trompe l’oeil shades were placed on models who sported a variety of prominent bang styles—heavy curtains of curls, bowlcuts, and short, piece-y fringes—an inspired choice that made the accessory all the more punchy. Oxford shirts were crumpled and trousers intentionally tailored to sag, revealing just a few inches of midriff when paired with shrunken light-blend wool sweaters in vibrant grass greens and more classic rich navy blues. These exaggerated proportions complemented color-blocked lug-sole sneakers that combined colors like printer-ink cyan and blood red and grape purple and Windows 95-ashen green, as well as buckled leather moccasin-style oxford shoes reminiscent of something you’d dig out of an older relative’s closet. Prada’s shirt-sweater-trouser-loafer uniform felt deliberate and impeccably constructed as to be expected, however Closer offered a more considered glance into exactly how details like worn leather, too-long pants, and unexpected pops of psychedelic floral prints can completely change the tone of an ensemble: ”The power of reality, in a world of the imaginary,” as stated in the press release.

Emporio Armani
Breeze settled in on the shores of Emporio Armani’s menswear collection, crisp from the oceans of silk, lightweight wool, hemp, and linen that graced the runway. Based on the freeness of nature’s horizons, “This collection takes the Emporio Armani man out of his usual metropolitan habitat, leading him on horseback across sunny rises, expanses of lavender and wheat fields stretching into the distance, pervaded by a sense of overwhelming independence,” as stated in a press release. The connection between man and nature was made most prominent through the color choices: sun-faded shades of beige conjured images of swaying hay and golden sand, made more vibrant with floral shades like bougainvillea and lavender. The 87-look collection also saw massively tailored jackets and trousers along with boiler suits in faded charcoal and sky blue as if the Emporio Armani man himself unbuttoned from a long work day and headed straight for a day at the oceanside. Deep-V sweater vests in oceanic herringbones with aquatic blues and seafloor-browns were styled with paper bag style trousers whose drawstrings resembled a sailor’s rigging. All signs pointed to a beachy escape for the Emporio Armani man, “abandoning touch city living and dressing to explore a fresh, enchanting softness and sensuality.”

Zegna
“Now that our reformed vocabulary has been established,” shared Alessandro Sartori in Zegna’s show notes, “it is the moment to focus on how items are or can be used, on the singular ways they mold to individual personalities.” The creative director’s approach to Zegna’s Spring/Summer 2025 collection infuses this idea into their Oasi linen, a unique fabric the brand has designed to “close the gap” in more ways than one: to be 100% traceable, or completely and circularly produced within their own sustainable fabrication system, and to build a bridge between high fashion and nature. Each silhouette felt easily tailored to the body, featuring different plies and layers of Oasi linen to create garments as dense as outerwear and as light as t-shirts. Rich-looking botanical printed jacquard knits expressed a warm-weather Italian spirit, while silk, cotton, and leather showcased natural shades of terracotta, sentiero yellow, and bianco Zegna—a signature white off-white somewhere between ecru and stark white. Zegna’s star has only risen higher with its manifold dedication to design while maintaining a demonstrable effort toward a more environmentally conscious fashion system.

Fendi
Fendi opened its first collection of its centennial year paying homage to family tradition. Creative Director Silvia Venturini Fendi presented a series of uniforms in smart plaids, broken pinstripe suiting jacquard, and soft-yet-masculine pastels that both revisit and reimagine the Italian brand’s first men’s collection in 1990. Fendi Club crests—small leather emblems boasting the house’s iconic selleria stitch—adorned the crisp wools and minimal silhouettes audiences know to expect from Fendi menswear,highlighting the house’s heritage as well as add a dimension of play to the airy garments. This season’s offerings sit “somewhere between sports and ceremony,” as stated in a press release: The Fendi Club patch is ample on breast pockets of polo and overshirts layered with silk ties and styled with pleated shorts or, in more whimsical looks, pastel green-checked Madras cotton trousers. As for the accessories, the selleria stitch was prominently featured on the signature Fendi Baguette and Baguette Double bags as well as a diagonal detail for buttery leather shoppers. Summer sport came to life with the FENDI Force sneaker, a whipstitched trainer with subtle logo accents. Shaped by 100 years of tradition, Fendi’s future is surely selleria-sewn and guided by a north star of Italian craftsmanship.

Martine Rose
Martine Rose brought alternative beauty to the main stage this season, with “the unusual, the unseen, the unpredictable,” as stated in a press release. The designer’s Spring/Summer 2025 show established a heady framework built on immediate contradiction. For example, despite a pristine Milan location and a prime fashion calendar spot, Rose opted for simple folding chairs and recycled curtains as scenography. And her perfectly tailored wool trousers revealed an unexpected leather crotch paneling with zipaways so they could transform into assless chaps. Rose thrives by presenting her work’s own artifice as a unifying design element (see her lumpy Nike Monarch sneaker collaboration from 2019), and this collection was no exception: many models wore prosthetic latex noses, hip-skimming weaves, and logo baseball caps pulled down so low they cast shadows over their eyes. The aim is to create a look Rose calls “confrontational” in the show notes. The impression left a deliciously stand-offish take on alternative beauty through her collection’s characters made anonymous by the cosmetic prosthesis and accessories. Leathers, blazers, and gowns were done in the designer’s signature sporty way, sculpted with off-kilter details like zippers that zip down instead of up, affixed with elbow and knee patches that nod to motorcycling culture, and of course, styled with meter upon meter of spandex. As is her calling card, Rose’s clothing did more than showcase her undeniable skills as a designer, but proffered a rich discourse on beauty and its infinite alternative forms.

DSquared2
Dynamic duo Dean and Dan Caten were at it again with a revealing portrait of fashion for their Spring/Summer 2025 show called #D2HEAT. Known for their maximalist approach to design, the pair brought a more unexpected gentleness to their usual sex-on-a-stick references to underground style. Punks and leather daddies were represented with studded creepers and biker jackets both done in soft-looking calfskin—the use of more delicate materials only turned up the heat, calling on sensuality in addition to the grittier eroticism associated with these subcultures. Sheer safe-for-work chiffon blouses were layered over quite NSFW bondage harnesses and teensy bralettes, a harmonious styling decision that unified the day-to-night transition with just a thin veil of silk. Lace, laminated jersey tanks, and ’80s-reminiscent office power-dressing revealed “the same stylish character’s nocturnal alter ego,” as stated in the show notes. The Caten’s steamy #D2HEAT reminds the fashion world of the innate sexiness of getting dressed, whether for work or play.

JW Anderson
“Are you feeling dreamy? Perhaps a little delirious? Is everything getting out of proportion?” In classic JW Anderson fashion, the designer opens his show notes with an evocative poem that lets the mind wander and be mystified by the runway. This season of the designer’s namesake brand combined collections for both men’s Spring/Summer 2025 and women’s Resort 2025 and is based on the larger-than-life dreams that came about in a perhaps-hypothetical-perhaps-true-to-life hypnotherapy session. The opening looks were exaggeratedly oversized liner jackets quilted in candylike pastel nylons like giant down comforters, ebullient bubble-hem coats reminiscent of waffle texture thermal fabric rendered 3D with layer upon layer of yarn, and cozy knits boasting a colorful pillow on each hip. The dreamlike arrangement unraveled into massive leather paneled coats, asymmetrical balloon sleeved suede tunics, and fisherman pullovers that read “REAL SLEEP,” paired with tiny skin-tight biker shorts, drop-crotch trousers, or tailored parachute-hemmed denim, always tucked into a pair of vintage military boots. Of the 56 looks in the collection, three boasted Guinness pints embroidered with pearls for the foam, a preview of JW Anderson’s collaboration with the 265-year-old Dublin brewery: a ready-to-wear capsule collection available later this November. From deep REM to the runway, this season of JW Anderson was a veritable feast of hypnotic silhouettes blown to fantastic proportions that, this fall, will pair perfectly with a Guinness.

Gucci
A fleeting glance between strangers: a delicate smile, a laugh, an eye-roll. These are the encounters—or incontri as shared in the press release—creative director Sabato De Sarno used to fuel his Spring/Summer 2025 menswear collection, his first men’s season for Gucci. Se Sarno expressed a minimal interpretation for the iconic Italian brand through simple uniforms: three-button single-breasted suits with high breaks and perfectly ironed sleeves, boxy tailored wool shorts paired with intarsia long-sleeve polo shirts, and three-pocket bowling shirts infinity-printed with summery motifs like lavender surfers and orange flowers. Leather goods included the Gucci B bag, a leather cosmetic case-looking top-handle with three detachable mini bags clipped on for additional bits and bobs needed for travel, as well as a new belt variety that used double-ended snap hooks to mimic the classic horsebit with a bit more of a contemporary twist. Shown in Milan’s Triennale di Milano, De Sarno succeeded in cultivating a sense of incontri: his garments felt lived-in when styled on the models who strode through the museum-turned-runway, passing by one another with ease.

Moschino
Creative director Adrian Appiolaza took a paper shredder to nine-to-five work culture with LOST AND FOUND, his Spring/Summer men’s and Resort women’s 2025 collection. With a desire to ditch urban life for an imaginary paradise, Appiolaza presented a runway full of the usual quirky fare—acrylic egg brooches and hats with other miniature fedoras glued on them, for example—this time telling a linear story from office clutter to on-holiday hobbyist. Early on, three-piece suits overflowed with the entire contents of a traditional work desk, calculators and staplers and pencils shoved into a dizzying series of jacket pockets, crafted for each item. Long ties snaked across the floor. Overcoats and tank tops were shredded like discarded official documents might be in a corporate setting. About half way through the 58-look collection came the power-clashed psychedelic floral print separates, women’s skirts fashioned out of giant printed silk panels (which became scarves on men’s looks toward the end of the collection), and even a suit whose trompe l’oeil pattern and accompanying red-and-white netted skirt transformed the model into a still-life view of a waterfront Italian dining table replete with gustatory delicacies. Leisure was perhaps best represented by the soccer references, done both literally (one knit bore a black and white hexagonal pattern that was rather unmistakable) and more cheekily: a pair of models traipsed down the runway, one in a skirt and jacket made to look like Italy’s flag with soccer balls superimposed, and the other in leather pants, and a white tank top whose boat neck was stained with blotches of ketchup. If the message wasn’t made clear by the final all-white ensembles paired with massive sunhats and floral vine necklaces—loosen your tie and go on holiday, you deserve to stain your shirt a bit.

Brioni
Creative director Norbert Stumpfl tapped into the solemnity behind Brioni’s quiet elegance for his Spring/Summer 2025 menswear collection, shown in the outdoor atrium of a Milanese palazzo. This season’s offerings included the brand’s bread-and-butter suiting rendered in a gorgeously neutral palette of grays, browns, and blacks with the occasional splash of aqua green or oceanic blue. This palette—inspired by the School of Rome painters from the early 20th-century—struck a marvelous contrast with the green of the palazzo’s courtyard. Trench coats, blouses, and precious leather jackets nodded to scaled-back leisurewear without compromising the fully-tailored glamor the brand is known for. This perfect slice of Italian tailoring provided just enough of a riff on the foundational wardrobe Brioni is known for: the perfect trousers, shirt, and jacket for any occasion.