For most of the last fifteen years, men's trousers had one direction: slimmer. This fall the line has softened. The fall 2026 menswear forecasts point to roomier, drapier tailoring and to wool trousers in brown and olive taking over from jeans on more days of the week, and search interest in pleated trousers has more than doubled over the past two years. The pleat is back, and this time it isn't just on the runway.
It's also the trouser men are most unsure about. Pleats sound like your dad's khakis, and a bad pair still looks exactly like that. A good pair looks relaxed, deliberate and more expensive than it is. Here's how to tell the difference and how to wear them.
What pleats actually do
A pleat is a fold of fabric sewn into the waistband at the front of each leg. When you stand, it lies closed. When you sit, walk or put your hands in your pockets, it opens and gives the trouser room through the hip and thigh. That's the whole point: comfort without the leg looking baggy, and a cleaner line from waist to shoe because the fabric drapes rather than clings.
That drape is why pleats suit fall. Heavier cloth such as herringbone, flannel or a wool blend hangs better with a little extra room at the top, and a trouser with some volume balances the bulk of a knit or a coat in a way a skinny chino never could.
Single, double or deep: choose your pleat
- Single pleat. The easiest way in. One fold each side, subtle enough that most people won't notice it's there. If you're switching from flat-fronts, start here. The Castellucci Herringbone Pleated Trousers are the template: a single pleat, belt loops, a clean tapered leg and a herringbone weave that gives the fabric texture without pattern. In brown, beige or gray, they're as autumnal as a trouser gets.
- Deep pleats. More fabric, more shape. These open across the hip and give you that fuller-at-the-top, narrow-at-the-ankle silhouette that reads distinctly fashion-forward. The Ricciardi Pleated Tapered Trousers do exactly this, with waist sizing in inches so the fit at the top is right from the start.
- High-waist pleats. The old-world version: the trouser sits at your natural waist, not your hips, and the pleats fall in one long line to the hem. It makes your legs look longer and your outfit look intentional.
Direction matters less than people think. Forward pleats (opening toward the fly) are more common; reverse pleats (opening toward the pockets) are the classic Italian tailoring choice. Both work. Fit is what decides whether they look good.
How pleated trousers should fit
Four checks, in order of importance:
- The pleats should lie flat when you stand. If they pull open while you're standing still, the trousers are too tight across the hip. Size up. This is the single most common mistake and the one that makes pleats look cheap.
- The rise should be mid to high. Pleats on a low-rise trouser have nowhere to go and bunch at the crotch. The waistband should sit at or just below your navel.
- The leg should taper. Roomy at the top, narrowing toward the ankle. A pleated trouser that stays wide all the way down is a deliberate statement (more on that below); one that stays wide by accident just looks big.
- The hem should touch your shoe with little or no break. Extra fabric pooling at the ankle undoes all the clean drape the pleats created. If you're between lengths, have them hemmed. With a tapered leg, a cuffed hem looks good and adds weight that helps the trouser hang.
The wide-leg version, if you want to go further
The most fashion-led take this season is the pleated wide-leg: high waist, deep pleats and a leg that falls straight to the floor. It's a strong look, so build the rest of the outfit to support it. Keep the top half closer to the body, such as a fine knit tucked in or a shirt, and wear a shoe with some substance so the hem doesn't swallow your foot. The Quaranta High-Waist Pleated Wide-Leg Trousers are the version to try, in gray, black, beige or white.
For the full old-world effect, there's the side-adjuster trouser: no belt loops, small buckles at the waistband instead. It gives a cleaner waist, and it's a detail you'll see on a lot of Italian tailoring. The Amedei High-Waist Side-Buckle Trousers pair it with deep front pleats and a high waist. Wear them with a tucked-in knit and nothing at the belt line competing for attention.
What to wear on top
Pleated trousers have volume at the waist, so the top half should be neat rather than big.
- A fine-gauge knit, tucked in. The most useful combination of the season. A crew-neck in a solid color, tucked fully into a high-rise pleated trouser, looks polished without needing a jacket. The Cassini Classic Wool Knit Sweater comes in sixteen colors; brown, beige or dark green sit naturally with fall trousers.
- A turtleneck. Same idea, more polish. Tuck it in, add a coat, and you have an outfit that works for dinner.
- An overshirt or blazer, open. If you want a layer, keep it at hip length so the pleats and waist stay visible. A long coat over a pleated trouser is fine; a short, boxy jacket that ends right at the waistband cuts the outfit in half.
Avoid oversized hoodies and long, untucked tees. Volume on top plus volume at the waist makes the whole silhouette shapeless. Browse men's knitwear for the tops that work best.
Which shoes work with pleated trousers
Because the leg is fuller at the top, the shoe needs a bit of presence to anchor it.
- Loafers. The natural partner, and the fall forecasts specifically pair chunkier loafers with heavier trousers this season. Wear them with socks in October. The range is in loafers.
- Chukka boots. The best choice once it's cold or wet. A tapered pleated trouser with a slight break over a chukka is one of the easiest good outfits in menswear. The Zappa Leather Chukka Boots in beige or black are a simple, clean shape.
- Clean leather sneakers. Fine with a casual cotton pair, never with wool or herringbone.
Skip anything slim and pointed. A narrow dress shoe under a roomy trouser looks lost.
Three outfits that work this fall
The weekday. Gray herringbone pleated trousers, a navy fine-knit crew tucked in, a brown belt and brown loafers. Office-ready without a tie, and warmer than it looks.
The earth-tone weekend. Brown pleated trousers, an ecru or beige knit, a twill overshirt left open, and suede chukkas. Brown is the color of the season, and texture (herringbone, knit, suede) does the work that pattern would otherwise do.
The evening. Black high-waist pleated trousers, a black or charcoal turtleneck tucked in, and polished leather boots. Tonal, sharp, and very Milan.
The short version
Start with a single pleat in a fall fabric. Make sure the pleats lie flat when you stand, keep the rise mid to high and the leg tapered, and tuck in a fine knit on top. Finish with loafers or boots. Once you've worn a pair that fits, flat-front trousers start to feel a little stiff.
Every style above is in men's trousers, and the knits, boots and loafers to go with them are in the men's Fall Drop. Pieces are already marked down, and buying more than one takes an extra 15% off two items, an extra 20% off three and an extra 25% off four.
Read next
- How to Wear Loafers: A Men's Styling Guide — the shoe that suits a pleated trouser best, in full.
- Fall Layering for Men: Building an Outfit From the Knit Up — what to wear over your trousers as the weather turns.
