Given the world’s current woes, we feared the Milan menswear shows would either be filled with boring, yet commercially safe bets, or escapist concoctions so fantastical that they’d be better classified as costume. Fortunately, neither was in evidence. Instead, many collections redefined their “classic” designs in a way that was tinged with intrigue and sharp appeal.

Christopher Bailey embraced the mood by liberally mixing Burberry’s heritage check with the pinstripes and patent leather of his more upscale Burberry Prorsum line. It was an unprecedented move, and, despite their overexposure, seemed to signal a renewed reverence for the brand’s roots. Raf Simons put a captivating twist on classic suiting, adding a slight curve to the waist and rounding the shoulders of his jackets for Jil Sander. The effect was powerful, yet sensuous, with sharper pieces, such as long line jackets and slim pants, which balanced out the femininity of the more voluptuous ones. Moschino’s Military Dandy was witty and refreshing, thanks to bold necktie-inspired stripes, combat boots and patchwork plaid trenches. Other designers used subtle detailing to add interest to otherwise standard menswear staples—think frayed hems at Alessandro Dell’Acqua, studded white shirts and Oxford shoes at Prada and floor length hemlines at Marni.

Good ol’ fashioned Americana also made an appearance, though the theme’s execution was not as stable as its popularity: John Varvatos’ perfectly worn, Marlboro Man-worthy biker jackets struck just the right chord, while Roberto Cavalli’s flamboyant riff on workworn denim and Navajo print was perplexingly misguided.

The classic approach also manifested itself in the form of comfort dressing. Garments radiated warmth and protection from the chills of the day: voluminous funnel necklines that appeared to swallow models’ faces at Dell’Acqua and Gianfranco Ferré; tantalizingly tactile leather trenches, suede trousers and nubby knits at Bottega Veneta; a collection of rich burgundy pieces at Etro inspired by red wine; swishy velvet trousers at Giorgio Armani that could have passed for pajama bottoms. And in a peculiar twist, the one item of clothing that best evoked cozy fire-front winter days—Dolce & Gabbana’s duvet-style quilted silk pants, complete with elastic sweatpant ankles—end up causing the week’s biggest melee, in the form of an intellectual copyright battle with Armani.

As for the inevitable escapist concoctions, we were pleasantly surprised to note that many of them could easily work off the catwalk. Even some of the less traditional pieces had a certain practicality that kept them firmly on the right side of ridiculous, from Alexander McQueen’s floor length cable cardis to Missoni’s Frankenstein Cosby sweaters and Gucci’s colorblocked shirts. There were, of course, exceptions—particularly the inflated shoulders and billowing arms on some of the Ferré jackets. In a different time we might have had a different reaction to the look, but in comparison with the blissful simplicity of everything else, the design’s intellectualism just seemed awkward.

—Erin Magner