Fashion is having a relaxed moment, quite literally. After years of slim-fit and tapered everything, the return of relaxed trousers feels like a breath of fresh air.
From the streets of Paris to the runways of Milan, this effortless silhouette has made its case, and men everywhere are listening. Harry Styles has already mastered it, Timothée Chalamet has given it his nonchalant seal of approval, and if you take one look at Mike Fait’s Challengers promo tour, you’ll see that relaxed tailoring is officially the future. The best part? Whether you’re going for old-money refinement or new-wave streetwear, these trousers fit seamlessly into any wardrobe.
The Power of the Drape
There’s something about a well-cut pair of relaxed trousers that just screams effortless. It’s the way they fall—clean, uninterrupted lines synonymous with quiet luxury.
When Saint Laurent sent models strutting down the runway in billowing, high-waisted trousers paired with razor-sharp blazers, the message was clear: the era of stiff, uncomfortable menswear is officially over. Prada doubled down with voluminous trousers tucked into sleek boots, and Loewe’s version consisted of wide-legged wool pants draped perfectly.
When wearing your pair, think about adding a bespoke silk scarf or a subtle piece of jewellery.
From Boardroom to Dinner
It’s rare to find a wardrobe staple that can swing between professional polish and downtown cool, but relaxed trousers are an easy bet.
A charcoal pair teamed with a fitted roll-neck and a structured coat screams boardroom authority. Swap the coat for a relaxed bomber and suddenly you’re stepping into a weekend coffee run with the kind of ease that feels both intentional and nonchalant.
The key is in the proportions; balancing the looseness with a sharp upper silhouette keeps things refined rather than sloppy.
The Hollywood Effect
If you need further proof that relaxed trousers have gone from a quiet rebellion to full-blown dominance, just look at the swish set. Jacob Elordi, the poster boy for modern masculinity, has made them his signature, pairing oversized trousers with fitted polos and statement coats.
Meanwhile, A$AP Rocky has taken the look into full high-fashion mode, mixing pleated, wide-leg styles with streetwear elements that make his ensemble effortlessly current. Even Lil Nas X, who once championed the era of skin-tight tailoring, is now opting for billowy silhouettes that make him look like he’s just stepped off a yacht in the South of France.
For your own wardrobe, experiment with bold footwear choices such as sleek loafers or modern trainers to instantly lend some edge to your relaxed trousers.
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The Streetwear Crossover
Relaxed tailoring has infiltrated the streetwear scene in a way that feels organic and completely on-trend.
Oversized trousers with vintage tees and chunky sneakers have become the spoken uniform for the ’cool kids.’ The pairing is decidedly casual and intentional, a masterclass in styling that feels like a whisper of revolt against everything hyper-fitted in the 2010s. When Justin Bieber rolls up in relaxed wool trousers, paired with an oversized hoodie and beanie, it’s not an outfit; it’s an extension of his personality.
The Art of Styling It Right
Here’s the thing about relaxed trousers: they’re a power move when worn right. The trick is to look sharp while letting the trousers take centre stage. For example, pairing a crisp white shirt tucked into pleated trousers will convey a quiet confidence.
For a more casual take, swap the shirt for a fine-knit sweater or even a slouchy hoodie, but keep the accessories sharp—think sleek loafers, or a killer watch. The balance between ease and elegance is what makes this trend so undeniably cool.
The Fabric Game
Not all relaxed trousers are created equal, and fabric choice plays a massive role in how they translate. Wool blends offer a structured yet fluid drape that works beautifully for evening wear, while linen versions deserve a permanent spot in your vacation wardrobe.
Cotton twill keeps things grounded and versatile, perfect for everyday wear, while technical fabrics are bringing a new-school edge to a classic silhouette. The key is in the movement, so look for trousers that swish, glide, and move with you.
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The Future of Menswear
Relaxed trousers aren’t just a fleeting trend. The days of struggling into too-tight pants are long gone. This is fashion that works with you, not against you. It’s about confidence, presence, and owning your space without needing to shout. So, if you haven’t already made the switch, consider this your sign.
