How To Find A Pair Of Jeans You’ll Want To Wear Forever

Two denim lovers share their top tips for finding a timeless style.

A model wearing dark blue jeans sits on a tall stool

(Photo: Everlane)

Looking to rustle up some excitement in your closet? For maximum versatility, there’s no better place to start than with a new pair of jeans. Toronto-based style expert Iva Grbesic, who appears regularly on TV’s CityLine, shares her easy-to-steal outfit ideas with 176k followers on TikTok—and 80 percent of her most-watched videos feature denim. Last year, Grbesic experienced a viral hit when a simple outfit consisting of jeans, a blazer and red heels captured 5 million views from around the world.  “It resonated with women everywhere because it doesn’t matter where you live or what you do, we all wear jeans,” she says.

They’re the hardest working, all-season garment in your closet and have the potential to be dressed up or down in an instant, so you can’t go wrong with a timeless pair of jeans that will make you feel amazing for years to come. Here’s how to find the perfect fit for you. 

Take your time

“What makes a timeless pair of jeans is how they make me feel when I have them on, regardless of what’s trending,” says Musemo Handahu, a Halifax-based visual storyteller. “If you feel your best and no one can tell you otherwise, then you are in your timeless pair.” Chasing trends is not only hard on your wallet, but fast fashion is also responsible for around 10% of all carbon emissions. Denim is one of the worst culprits, and it takes 7,500 litres of water to make a single pair of jeans. 

Here’s the crucial first step to find a pair of jeans you will wear for years to come: be patient. “If you’re going denim shopping, you’re going to have to spend some time on it,” says Grbesic.

Try something new

To start, Handahu suggests trying a shape that’s new to you. “I got tired of feeling like I should always wear skinnies to elongate the leg and look leaner as a person who lives in a plus body,” she says, of the style she wore exclusively until a few years ago, “So I explored other styles and ended up finding fits that allowed me to be myself in other silhouettes.” Her current go-to style is the Sky-High Straight Cut from Old Navy, which is available in size 0 to 30 and often sell out. “After trying my first pair, I was hooked,” she says, “They sit at the right part of my waist, have plenty of room for my belly, are long enough for my 5’11 frame, and my calves aren’t suffocating.”

Go beyond trends

Grbesic hasn’t worn skinnies in a while either, but she includes them with straight and bootcut styles on her list of recommendations with longevity. “It’s good to have more than one option because we’re all different, and if you navigate within any of those three styles you’ll have a pair that will last you five years,” she says, “And that’s a good lifespan to expect because our bodies change.” She discovered the blueprint for her dream jeans, a high-rise bootcut with subtle volume in a medium to dark wash, after having her fourth child. “A bootcut can help balance a frame if you have a curvier butt or thighs. And they offer a peekaboo moment for your shoes,” she says. Predicted to come back in a big way, bootcut and flare shapes were recently spotted on stylish celebs such as Jennifer Lopez and Jennifer Aniston. But there is one key detail to look for to secure a classic vibe: the rise (aka where the waistband sits on your torso). No matter what’s trending, choose a classic mid- or high-rise fit only, and that applies for any style of jeans you choose. “My number one fashion regret is low-rise denim, and you can put that on my tombstone,” says Grbesic.

Get the right fit

Once you zero in on a cut that speaks to you, you’ll want to nail the perfect fit. That may be found right off the rack, or it might be achieved with the helping hand of a tailor. “As long as it fits around the largest part of you, whether that be your butt or waist, then everything else can be taken in,” says Grbesic. She also prefers a wash with subtle dimension rather than a flat colour. “Denim can be a living thing, and some variation gives it a bit more depth and makes it more interesting,” she says. “Jeans with some fading will also look better over time.”

Lengthwise, straight and skinny styles have traditionally been easiest to wear interchangeably with both heels and flats. And you can always roll up a cuff, Grbesic points out. Bootcut jeans can offer flexibility as well, especially with the latest styles that are cropped around the ankles. If you choose a full-length cut, adjust hems to hover over the ground so it doesn’t get frayed and dirty.

Consider your options

If you’re shopping IRL, it always helps to take a couple of pairs of jeans into the change room with you. “My favourite thing about denim offerings for plus bodies in the past few years is that brands are feeling more confident exploring a much wider range of silhouettes. It’s such a joy to see bodies like mine in different cuts.” says Handahu. With a few options on hand, you can compare fits across brands, styles, or even colours. (Black denim tends to have less stretch, for example.) The strategy works to increase success with online shopping too. “If you can afford it, I would recommend ordering multiple sizes–knowing that you’re going to send some back,” says Grbesic. (Just keep in mind that this practice contributes to the fast fashion cycle and returns sometimes end up being thrown away, so be mindful.)

And enhance your head-to-toe effect, which is a nice way of saying don’t shop dishevelled. “Make yourself look and feel your best, and then try them on,” says Grbesic, “It doesn’t have to be full glam, but do your hair and makeup, and your jeans shopping experience will be a lot different.” So, whether you’re planning a meet cute with new jeans at the mall or in your bedroom, put your best face forward and you’ll start a years-long love affair on a high note.

Below, some styles that will stand the test of time.

A pair of high-waisted straight jeans from Old Navy

Old Navy High-Waisted O.G. Straight Jeans

This popular style keeps selling out, so keep an eye out for the next restock.


A model wearing a pair of straight jeans from Mavi

Mavi Kendra Mid Supersoft Straight Leg Jeans


A pair of dark blue straight jeans from Penningtons

d/C Jeans 1948 Fit Straight Leg Jeans


A model wearing dark blue jeans sits on a tall stool

Everlane The Rigid Way-High Jean


A model wearing a pair of black jeans from Banana Republic

Banana Republic High-Rise Flare Soft Sculpt Jeans


A model wearing a pair of blue flared jeans from H&M

H&M Flared High Jeans


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