5 Menswear Trends to Know From Milan Fashion Week SS27
Milan has spoken: bigger suits, rogue waistcoats, office dressing, and battered leather are about to have a very big moment
- Expect roomier suits, relaxed tailoring, and standalone vests to loosen up the traditional menswear uniform.
- Deconstructed tailoring and beaten-up leather bring visible construction and lived-in character to the wardrobe.
The Milan menswear trends about to be everywhere
Milan Fashion Week has never been particularly interested in telling men to play it safe, and the Spring/Summer 2027 collections were no exception. This season, the suit got roomier, tailoring came apart at the seams, office dressing made an unexpected comeback, and leather looked better with a few battle scars.
The message is straightforward: polish is still welcome, but perfection is getting boring. If you’re planning the wardrobe ahead, these are the five trends worth knowing.
Big suit energy
The skinny suit can stay in the past
For SS27, tailoring is getting bigger and more relaxed. Jackets are generous through the body, trousers have space to move, and the whole silhouette doesn’t feel as if something designed to impress an HR department.
The trick is proportion. If the jacket is big, let it be big. Pair it with generous trousers rather than trying to balance an oversized blazer with something skinny. Go for a relaxed jacket and wide-leg trousers, then keep the rest relatively clean. A crisp shirt or a simple tee will let the silhouette do the talking.
Deconstructed
This season, the seams are showing
SS27 tailoring is taking the suit apart and refusing to put everything back where it was found. Exposed construction, unfinished edges, displaced panels, and disrupted silhouettes turned traditional tailoring into something far more interesting.
The appeal is that it makes even a familiar jacket feel unpredictable. You don’t need to dress like you’ve just escaped a fashionFashionThe art and industry of designing, producing, and styling clothing, footwear, accessories, and beauty trends. It reflects cultural influences, personal expression, and evolving styles across seasons and markets.Go to Fashion Glossary-school pattern-cutting class, either. One deconstructed piece is enough to make the point.
Look for jackets with visible seams, asymmetric panels, or unfinished details. Keep everything else straightforward.
Boardroom bound
Yes, the office is back. No, you don’t have to hate it
The tie, crisp shirt, and tailored trousers have returned, bringing a little corporate discipline back to the menswear wardrobe. Start with a good shirt and trousers, then add a tie with personality. Loosen the proportions elsewhere and avoid looking too perfectly pressed.
Vests
The waistcoat is going solo
For years, the vest has been the third wheel of tailoring, squeezed between a shirt and jacket and rarely allowed to have much fun. SS27 changes that. The vest is stepping out on its own, worn with trousers or layered over shirts as a proper focal point. It brings structure without the full weight of a blazer, making it particularly useful when the weather starts doing its usual summer nonsense.
Try a tailored vest with relaxed trousers and loafers. For something less formal, layer one over a simple shirt or tee. The important thing is to let the vest breathe. It has spent enough time underneath the jacket.
Beaten leather
The more lived-in, the better
Forget leather so pristine you feel guilty touching it. SS27 is after something with a little mileage.
Scuffs, creases, faded finishes, and worn surfaces gave leather a more relaxed attitude across Milan. The ideal jacket looks as though it has already been to a few gigs, missed a train, and survived a questionable night out. Which, frankly, is exactly what you want from leather.
Frequently Asked Questions
The key SS27 trends include oversized tailoring, deconstructed suits, office-inspired dressing, standalone vests, and beaten leather.
Yes. Milan’s SS27 collections favor generous proportions, roomier jackets, and wider trousers for a more relaxed take on traditional tailoring.
Yes. Ties, crisp shirts, and tailored trousers are returning for SS27, but with more relaxed proportions and a distinctly fashion-forward attitude.
The vest can be worn as a standalone piece with tailored trousers or layered over a shirt or T-shirt. The key is to treat it as the main event rather than simply part of a three-piece suit.
Lived-in leather is the look for SS27, with scuffs, creases, and faded finishes replacing perfectly pristine surfaces. The more character the leather has, the better.
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