You’ll need something equally precise up top, and that’s where a neatly cropped jacket comes into play. It should hit you right on the hip or just above it, defining your waist and streamlining your fit. If you’ve got the budget, the French label Lemaire is where to look. If not, the brand’s founder and co-creative director, Christophe Lemaire, also designs an estimable range for Uniqlo.
Tuck Your Tee Into Pleats
One bonus of wider cuts is that they offer a broader canvas for design details. In particular, it’s well worth exploring deep-pleated styles: on roomier pants, cut higher on the waist, they’ll bring an element of Armani-like sprezzatura. It’s also particularly effective during warmer months, when you can opt for neutral shades in lightweight fabrics: cottons, linens, and even silks are worth considering.
Of course, a pleated pant only works if you can see the pleats, so these are best worn with a t-shirt, neatly tucked in. Ideally, look for something with a bit of texture: we’d recommend looking into Lady White Co., the LA brand who’ve produced what might just be the perfect white t-shirt. And if you’re not feeling quite toned enough to rock a tee solo, layer a lightweight jacket or unbuttoned overshirt on top.
Channel Your Inner Lounge Lizard
If you’re really dressing up, consider going in a more louche direction: In a sea of guys sweltering in too-tight suits, why not waft through them in artfully relaxed tailoring? The 70s-tinged, gently oversized look has been steadily gaining traction over the last few years, and has become a uniform for everyone from Harry Styles to Donald Glover. Thankfully, it’s an easy look to rock for events beyond the Grammys.
A pair of pleated, wool-based trousers should be your foundation, and should be cut to pool gently over your shoes. Brands like Saint Laurent do it best, but more affordable versions can be found at labels like Studio Nicholson, Mfpen, and even Massimo Dutti. Tuck in a Cuban-collar shirt in a soigné fabric (ideally a silk-mix, for maximum flex), and wear with leather loafers. Sunglasses are a welcome addition, too—just take them off inside, unless you really want to push it.
Tips for Wearing Wide-Leg Pants
Pay Attention To Proportion
There’s no hard-and-fast rule about how wide is too wide: it’s a question of proportion, so it’ll depend on your height, build, and what you’ll be wearing them with. But speaking broadly, a 20-inch leg opening is a good ceiling—it’ll look intentionally roomy, but not comically oversized. As for fabrics, a wider leg should either have structure or drape, meaning your pants are best in a stiff, sturdy cotton or a fluid, relaxed wool. Anything too lightweight has a higher likelihood of flapping, and anything too synthetic can be prone to humiliating rustling. It’s also generally wise to opt for styles that sit a little higher on the waist, as they’ll create a cleaner line without adding bulk around your hips.
Keep It Tidy Up Top
After you figure out just how wide you’re comfortable with, it’s about balancing the proportions with the rest of what you’re wearing. Look for neater shapes up top: fitted, tailored, or slightly cropped pieces will help you stay the right side of sloppy. And don’t be afraid of boxier styles: a well-chosen bomber, Eisenhower, or four-pocket jacket looks killer with a roomier cut of jeans. It’s generally wise to avoid longer-length coats, or oversized shapes, which tend to have a stumpifying effect.
Pick Your Break, and Stick To It
You’ve got two options here: cropped, or puddling. The former means you want the pants to stop right at the ankle, to reveal a sliver of sock before the top of your shoes. It works best for chinos, jeans, and other ‘day’ pants, especially if you’ll be wearing them with sneakers or thicker-soled lace-ups. Your tailor can hem them to the right spot, but sturdier cottons and denim will look just as good when neatly rolled up. A note on that: you want a maximum of two rolls, each an inch wide, or they’ll look bulky.
If you’re taking the puddling approach, the pants should rest lightly on the top of your shoes, pooling gently in a way that looks deliberate, not messy. This works best with more fluid fabrics, but can work with casual styles, too: if in doubt, pull up almost any recent picture of A$AP Rocky’s pants, and take that as your cue.
Keep Shoes on the Sturdier Side
Here’s the good news: wider cuts will play well with the majority of men’s footwear. But they’ll really get on with more substantial styles: a pair of lace-up derbies, chunky loafers or Red Wing boots will balance the proportions perfectly. As for sneakers, anything with a bit of heft is best: you can’t go wrong with Nike Air Humaras, Asics, or a classic pair of Chucks. Just avoid anything too dainty: a skinny-soled loafer or narrow running shoe peeking out from beneath a wide pant is likely to make your feet look tiny.