MILAN — Hanging floor to ceiling and wall to wall around a gallery in month-old Fondazione Prada on the outskirts of this city, there are dozens of paintings belonging to Miuccia Prada and Patrizio Bertelli. The salon-style installation plays off the time-honored convention of collectors exhibiting their holdings as a way of displaying their superior tastes.  At the core of Ms. Prada’s perverse brilliance has always been her ability to flout the conventions of taste even as she recasts them. And you would be hard pressed to find a better example than how her pictures are hung: William N. Copley crammed in beside Lucio Fontana, Mario Schifano next to Jeff Koons, Alberto Burri on top of Gerhard Richter and butting up against Goshka Macuga.  It’s an aesthetic mosh pit, full of images and references that complement or antagonize each other, or slug it out for primacy.  Much the same impulse seemed at play in Ms. Prada’s men’s wear show, as roughly half of what she sent onto the runway was women’s wear. In one sense, she was merely falling in line with the new ambisexuality, a trend that motivated the venerable English department store Selfridges to merge its men’s and women’s sections onto three unisex floors this spring.  Naturally, though, Ms. Prada pushed gender blur into new territory. Partly this owed to her dedicating much of the spring 2016 men’s show to a resort collection for women, her own witty take on hoodlum chick looks from the ’60s, replete with pencil skirts, cat-eye makeup, ratted-up Rita Tushingham hairdos, pointy-toe narrow flats aerated with grommets and slouchy lightweight paillette-covered coats that shouted ka-ching.  Yet what seems like Prada’s continuing fascination with neoteny, the retention of juvenile traits into adulthood, was powerfully underlined here by a collection that presented guys with mop-top hairdos wearing topstitched Boy Scout shorts with weird dropped crotches; zippered geeky mock turtlenecks; sweaters patterned with Instagram-ready retro rockets and bunnies; socks over socks; ties worn on top of sweaters; and studiedly awkward leather jackets that were roomy at the rear and rucked up in front. As the painting show at her foundation makes plain, Ms. Prada’s is the kind of intelligence that tends to answer a question with additional questions. Here, the question was when and how and by what precise standard we decide that a boy is a man.  “I like that a guy doesn’t have to think so much” about getting dressed, Italo Zucchelli, the sunny Calvin Klein designer, said backstage before his show on Sunday. “The attitude is very simple. It’s all about unfussiness.”  That assertion was borne out in an exceptionally assured show whose apparent ease was in no sense easily achieved. At first glance, the blue or khaki jeans and jeans jackets looked like basics most men already have in their wardrobes. But for the parabolic waistbands draped from the trousers, a lot of the stuff could have come direct from Levi’s. Yet when you looked closer, it became clear that the fabric was jacquard made to resemble denim and that Mr. Zucchelli had trumped the many other designers now straining the limits of fabric technology to achieve deceptive trompe l’oeil effects.  “Maybe this guy wants jeans but not ordinary jeans” when he reaches into his closet, the designer said. “Maybe they want something that has a little added interest.”  The tale Mr. Zucchelli often has to tell on his runway has its basis in what he calls the Calvin Klein DNA, or to put it another way, the brand’s narrative.  Talk of brand DNA is not metaphoric to Angela Missoni, whose parents, Ottavio and Rosita, founded a company that she and a brother, Luca, continue to operate. (A third sibling, Vittorio, disappeared in a plane crash off the coast of Venezuela in 2013.)  If the zigzag patterned knits Missoni has been producing more or less continuously since 1958 are woven into the story of their family and its business, they are also threaded through a larger one involving Dolce Vita Italy.  For many years the Missoni family has vacationed at the Hotel Il Pellicano, overlooking Argentario Bay near the Italian resort town of Porto Ercole. It’s the kind of seaside place whose magic has long attracted swanky international types, global industrialists and European aristocrats in about equal measure and that has an almost ineffable glamour that only the photographer Slim Aarons has ever come close to capturing.  Missoni collections, seldom varying much from one season to the next, are best when they evoke atmosphere like the ones in Mr. Aarons’s pictures of Hotel Il Pellicano. The current one did so beautifully. How the subtle soft suits, washed-out patterns based on Madras cloth and ikat, pocketed field jackets, handsome hard-sided Globe-Trotter luggage lined in Missoni fabric might translate to other, less fantastical summer settings is hard to calculate.  They did, however, make at least one viewer want to pack a bag immediately and head for the Tuscan coast.  “People are ready to change the way they look,” Alessandro Michele, the creative director of Gucci, said backstage on Monday. “Fashion is not just a story about a dress or azure blue is the color of the season. It can translate a lot of things.”  In Mr. Michele’s first complete men’s wear show for the label since taking over in January, he doubled down on translating a cultural moment in which most everything about gender as traditionally constituted — genitals to pronouns — seems up for grabs.  He did this through a casting so androgynous it was tough to tell the boys from the girls; through a lavish use of materials, techniques and effects (crochet, embroidery, appliqué, eyelet lace, metallic mesh) usually associated with things “feminine”; and through shapes so generally body-obscuring they supported the notion that gender is more about what’s in your head than in your pants.  If it was a daring move for a luxury goods behemoth to undertake, it was, broken down into its component parts, probably not an uncommercial one. Runway shots of guys wearing butterfly shirts or pajama suits with lace ruff collars may draw hoots (and comparison to Valentino). But just as you can’t take at face value the pretentious show notes quoting the French philosopher Guy Debord on the practice of aesthetic mash-up he labeled détournement, you want to give breathing room for Mr. Michele’s lofty, if slightly loopy, aims.  So what if some of what he showed looked as though it belonged on a rag doll you won at a carnival ring toss? It was fun to watch. As models paraded down the concrete halls of a former goods depot, another philosophical quotation, this one printed on a wall of a hatter’s display stand at the Pitti Uomo trade fair in Florence last week, suddenly sprang to mind.  “Life is a cabaret, old chum!” it said. The attribution was to Roland Barthes.
At Prada, roughly half the men’s show was the women’s resort collection, while Gucci was just fun to watch.