For over a decade, slim-fit and skinny pants dominated menswear. Even after the ultra-skinny jeans fad tapered off a little in the early 2010s, almost every major clothing brand was selling pants in variations of slim and skinny, with pants starting thin and getting thinner as they tapered toward the bottom. In 2025, it’s safe to say that wide-leg trousers aren’t “making” a comeback; they’re back. You’ll find wider cuts everywhere, from high-fashion runways to the wardrobes of style-conscious men embracing a more comfortable, sophisticated silhouette. This shift aligns with the broader movement toward relaxed tailoring, which prioritizes ease of movement, soft draping, and timeless elegance.
Let’s break down a history of wide-leg trousers, why they’re back now, and how to incorporate a fuller cut of pants into your wardrobe without looking dated or overly trend-hungry.
A Brief History of Wide-Leg Trousers
1920s–1950s: The Golden Age of Full-Cut Trousers
In the early-to-mid 20th century, full-cut trousers were standard in menswear. Hollywood icons like Cary Grant and Fred Astaire epitomized effortless elegance in pleated trousers that draped beautifully with movement. These high-waisted, wide-leg pants offered both sophistication and comfort.
1970s: The Flare and Oversized Revolution
By the 1970s, wide-leg pants took on a bolder edge, with flared and exaggerated silhouettes becoming mainstream. From rockstars to disco kings, looser fits became synonymous with rebellion and individuality.
1990s–2000s: The Streetwear Influence
Fast forward to the late 90s and early 2000s, and oversized trousers made a comeback in skateboarding, hip-hop, and avant-garde fashion. While some styles bordered on baggy and extreme, they still influenced today’s more refined take on relaxed tailoring.
Why Wide-Leg Trousers Are Back in Style
- A Rebellion Against Skinny Fits: So often, new fashion trends are a reaction to the current standards. So unsurprisingly, after 15 years of slim and skinny fit, a wider style of pant was almost inevitable.
- Comfort-Driven Menswear: The pandemic introduced the idea that work and comfort could exist in the same place. With a return to office, wide-leg trousers provide breathability and freedom while maintaining a polished, tailored appearance.
- Influence from Luxury Brands & Designers: Brands like Brunello Cucinelli, The Row, Lemaire, and Bottega Veneta have championed relaxed tailoring, proving that loose-fit dress pants look incredibly elegant when styled correctly.
- A Shift Toward Classic Menswear Aesthetics: In the last few years, terms like quiet luxury and old-money dressing have become popular, reviving interest in classic menswear, which shares a lot of overlap with those aesthetics. Full-cut trousers naturally align with this refined, understated style.
- The Celebrity & Street Style Influence: Actors like Timothée Chalamet, Jeremy Allen White, and Brad Pitt have embraced high-rise trousers and relaxed fits, inspiring modern menswear enthusiasts to do the same and fashion brands to chase that interest.
Wide-Leg vs. Baggy: What’s the Difference?
There’s a difference between wide-leg trousers and baggy pants. While both are popular right now, the distinction is important.
- Wide-Leg Trousers: Tailored, structured, and designed to drape elegantly—they create intentional volume without excess fabric bunching.
- Baggy Pants: Intentional use of excessive fabric compared to the length of the leg, creating pooling at the ankles and an unstructured fit.
How to Wear Wide-Leg Trousers in 2025
The key to wearing wide-leg trousers successfully is to focus on proportion and balance—pair them with fitted shirts, structured jackets, or cropped outerwear to maintain a clean, intentional silhouette.
Casual Looks: Elevated Everyday Dressing
- Pair wide-leg pants with a polo shirt or knitwear for a sophisticated casual look.
- Loafers, minimalist sneakers, or Chelsea boots keep the outfit refined.
Smart Casual: The New Business Casual
- Tuck in a dress shirt or pair high-rise trousers with a lightweight blazer.
- Stick to neutral tones (beige, navy, charcoal) for a polished aesthetic.
Tailored/Formal: The Modern Suiting Approach
- Opt for pleated trousers in lightweight wool or linen blends.
- A double-breasted blazer beautifully complements the volume of relaxed trousers.
- Finish with oxfords, derbys, monk strap shoes, or loafers for a timeless effect.
Should You Try Wide-Leg Trousers?
We say yes. Granted, we’re biased because we like the look. But, the return of wide-leg trousers isn’t a short-lived trend—it’s part of the larger shift toward relaxed tailoring and timeless menswear. Whether you’re drawn to the comfort of more room in the leg, the elegance, or the rich history of full-cut trousers, there’s no shortage of reasons to give wed-leg pants a go.
If you’re ready to incorporate relaxed tailoring into your wardrobe, explore Proper Cloth’s selection, ranging from wool to linen. If you’re intrigued but not sure where to start, get in touch with a stylist who can help you find the perfect size. For some reading on wide-leg trousers, check out Esquire’s write-up on the topic.