While 2023 was most definitely the year of going pants-free, fashion girls who did opt for bottoms often gravitated toward roomier silhouettes. Just look to Hailey Bieber and her parade of baggy blues — or perhaps the forever trend-defining Rihanna, whose loose leather trousers are still on our shopping lists. But while a fashion moment that champions comfort is worth high praise in our books, it’s admittedly hard to find the right shoe combination for a pair of relaxed fit bottoms.
For one, unless you’re quite tall you’ll need to pay a visit to the tailor. And when you do, there’s the tricky question of deciding which footwear to hem them for: flats? Block heels? Tall boots? After all, it’s a rather permanent choice that will completely transform the aesthetic of your look. (No pressure!) Wearing them with square-toe ballet slippers? You’ve got chic Olsen vibes! Adding in some pointy toe boots? It’s giving polished and ready for a day of meetings. In other words, wide-leg pants require a bit of effort — but — when done well, the end result is entirely worth the energy.
So, in short, what is the best footwear to put with wide-leg pants? “I have two answers to this question,” says celebrity stylist Kate Young, who recently debuted a capsule collection with Splendid (which, ding ding ding, has more than one pair of amazing long and loose pants in it). “The first is a sort of chunky platform boot with the pant hemmed to fall over it to the floor. The second is what I do for daily wear: I hem the pants for flats and wear a white sneaker along the lines of a Stan Smith or Vans shape.” Young nods to this latter mash-up as a perennial favorite due to its laidback ease. “I love wearing these pants with sneakers or slide sandals as it's so much more chic than sweatpants or jeans — and just as comfortable.”
Other timeless options include heels with pointed toes. “Right now we are seeing a comeback of the pointy shoes, either a slingback or a boot are great options,” Le Point Founder Pauline Montupet says, calling attention to the fact that wide-leg pants are being worn looser and slouchier nowadays, which means a pointy shoe achieves that peek-a-boo effect. “Usually wide leg pants have a more menswear or stolen-from-the-boys feel, so the pointy toe feels really sexy and feminine with it, giving good tension to the outfit.”
If you’re not one to steer toward a more “classic” mix, rest assured there’s plenty of other routes to follow. “Flats often seem more intimidating with wide-leg pants (especially for petite frames), but I really love a square-toe ballet flat,” Montupet says. Or there’s one of 2023’s other biggest trends: Mary-Jane flats. "I love a Mary Jane,” Young says, adding that Le Monde Beryl’s take on the shoe shape is a recent favorite of hers. “They're ballet flats and Mary Janes, but so creative and subversive. There are sexy ones and demure ones, and then I love the Mary Janes with a little double silver buckle (Michelle Williams wore these with the green Splendid look to our launch dinner).”
Ultimately, it seems, the key to nailing the shoes-with-wide-leg-pants situation is this: don’t always abide by ‘the rules’. “Mixing both traditional and non-traditional elements provides an opportunity to express individuality and make a unique fashion statement,” Dāl The Label Founder Dana Mortada says. If a pair of pants looks like it’s supposed to go with a certain pair of shoes, maybe try it with something unexpected to make sure it feels personal to you. But for those who do well with guidelines, consider the following: “I would avoid anything with too rounded or short of a toe,” Montupet says, noting it will get hidden in the look. “Also, you need to decide if your pant is going with flats or with heels,” Young says. “Do not wear wide-leg pants with heels that bring the hem off the floor — that just looks bad — they need to skim the floor.” Ipso facto, decide which shoes you’re going to wear with your wide-leg pants and hem them accordingly.
Keeping these expert insights in mind, continue ahead for a few outfit ideas to help you nail your next leggy trousers moment.
Style a pair of easy-fit corduroys with square-toe dancer-inspired flats for a rebellious take on the #balletcore trend. The look can easily translate to cooler temps by knotting a chunky knit around your shoulders.
Touch of Texture
One thing you want to avoid is having your shoe get ‘lost’ beneath the hemline. There are a few ways to avoid this, including slipping into a pair of shoes with noticeable texture, like Khaite’s western-inspired studded wedges.
Pop of Sock
If you’re test driving wide-leg pants with flats but are reticent about the proportions, consider layering in a contrasting sock. Beyond adding a touch of nonchalant cool to the entire look, it also helps connect the hemline to your shoe.
When in doubt, it always helps to stick to a color scheme — especially since shoes in a similar hue to your bottoms will have a wonderful leg-lengthening effect. You can see this theory in action above, where cream loafers stretch out the silhouette of crisp white jeans.
For a pairing that’s both unique and elongating, style white or cream-hued wide-leg pants with loafers in a similar palette. The look is lovely for all seasons, and breaks away from the corporate associations some wider trousers have.
Sleek & Pointed
If you’re new to wide-leg pants and need a pair of shoes that will reliably ‘work’, look no further than pointed toe pumps or slingbacks. Sleek, simple, and enduringly polished, this duo will never go out of style.
Live for an ugly shoe moment? Us too. That’s why this wide-leg pant and chunky footwear combination feels like the perfect illustration of the Wrong Shoe Theory. While this wouldn’t necessarily work in a professional environment, it’s undeniably cool for everyday wear.