How to style bootcut jeans: 7 outfit ideas for every occasion

You may not have thought about how to style bootcut jeans since they were last popular in the '90s, but they're back. Having had a fashion makeover, it's all about styling bootcut jeans in a directional way to look like a trend-setter rather than a fashion-throwback.

Bootcut jeans began their style reign back with cowboys and ranchers where the slight flare at the bottom of the jeans ensured they worked well with the best cowboy boots. Last popular in the '90s, the sudden burst of Y2K nostalgia that swept through recent seasons, has brought bootcut jeans back to the fore, making them some of the best jeans for fulfilling the hottest denim trends of 2023. 

"The boot cut has patiently been waiting in the wings for the skinny to move over!" says denim stylist Sam Remer, who offers a Virtual Jeans Fitting Service on ilovejeans.com. "It's definitely time for this universal style to be brought out again. It seems whenever the flare or wide-leg jean is on trend, the bootcut is a diluted favourite that becomes the go-to shape. Gen Z's love of all things '90s and can’t get enough of the bootcut shape either with a high-rise waist or a low rise.”

Slightly tapered in the thigh area and wider from the knee to the hem, creating a small flare, it’s no surprise that these jeans have had a comeback, as they're universally flattering. But it's learning how to style bootcut jeans that will take from the '90s into 2023.

Sam Remer

Sam Remer is a Personal Denim Stylist & Shopper. Founder of the denim blog ilovejeans.com. She has found 1000’s of women great fitting jeans focusing on their body shape, size and budget. Offering online /in-store shopping sessions. Sam’s styling experience spans over 3 decades, choosing solving denim dilemma’s for all women to be her super power.

How to style bootcut jeans 2023: 7 bootcut jean outfit ideas

“Bootcut jeans are brilliant for most body shapes, as they balance out a curvy hip, bigger booty, elongate a petite frame and give shape to a lean figure,” says Sam.

A good all-rounder jean, they also work for many different occasions from dressed down walks in the park to drinks in the pub, looking especially polished with the addition of a heel.

While the low-rise waist is back on the runway, thankfully most modern-day bootcut jeans come with an easier-to-wear mid or high-rise waist. That's not all that's changed since their '90s inception. Silhouettes are slightly slimmer, and lengths range from cool cropped kick-flares to longer, puddle-length jeans. Although all reference '90s fashion trends at their core.

As with any flared jeans, the key to how to style bootcut jeans is to balance out your look by keeping the top half a little more fitted. Finding stylish tops to wear with jeans that highlight your torso will automatically balance out the width of the hem of a bootcut jean.

If you’ve not pulled on a pair of bootcut jeans since Jennifer Aniston had the 'Rachel cut', here are 7 outfit ideas to ensure you look contemporary.

1. How to style bootcut jeans with a blazer

“Bootcuts are a universal style and can be dressed up with a blazer or worn more casually with a leather jacket,” says Sam.

If you’re wondering how to style a blazer with this type of jeans, go for one that hits your thigh area to help give balance. Too short a jacket, may look too boxy, while too long could swamp petite frames. It's also better to choose a slightly fitted blazer, which will not only help emphasize your waist but also keep everything looking neat.

The perfect combination for smart casual outfit ideas, a blazer and bootcut jeans work best with heels, especially if you have longer-length jeans. As for what to wear underneath, a pretty blouse or shirt makes your outfit instantly smarter, whereas a t-shirt or jumper adds a casual vibe. 

2. How to style bootcut jeans with a sweater

Ditch the chunky knits when it comes to how to style bootcut jeans and instead embrace a cropped or slim-fitting sweater from one of the best knitwear brands to usher in the new season. It’s also a good idea to choose the more modern high-waisted bootcut jean and leave the low-waisted variety for warmer months. If your jumper is too long, do a French tuck so you have more of a waist.

When it comes to choosing the best bootcut jeans contrast your denim against a brightly coloured knit but don't just stick to blue bootcut jeans. Primary shades mixed with cream or white jeans make for a modern take on the jean and sweater look and can be worn all year round – just switch your heavier jumper for a skinnier cotton knit come from spring through to autumn.

While trainers will give this look a more casual vibe, if you opt for the longer-length bootcut jeans, try a platform boot or shoe to make the look feel dressier and tap into the autumn/winter shoe trends 2023 in the process. Pop a shirt under your best jumper and you've got a look suitable for less corporate workplaces as well.

3. How to style bootcut jeans with a shirt

When it comes to how to style bootcut jeans with a shirt or blouse, the best shirts to choose from are those that can be tucked in easily to show off your waist and balance out the small flare at the bottom.

If you want to wear something less fitted, how to wear oversized shirts with bootcut jeans still will involve either a little French tuck at the front or wearing them over a more fitted or waist cropped top, to ensure you have some midriff definition.

And when it comes to how to style jeans with a bootcut and a denim shirt, this look is the perfect candidate for double denim.

“As a denim stylist I’m an advocate for double denim and styling a long denim skirt or pair of jeans with a denim shirt tucked in or a cropped denim jacket,” advises Sam.

Just ensure that the denim is of a similar shade to not only create a coherent look, but also a slimming jeans outfit.

4. How to style bootcut jeans with a top

The rule of thumb for how to style bootcut jeans is to ensure the top half is sleeker and more contoured in order to balance out the flare at the bottom.

“If you’re following the trend for voluminous jeans then counterbalance what you put on the bottom with a tighter top, shirt or jacket,” says Sam. 

For this reason, slim-fitting t-shirts and tops work best with bootcut jeans. A cropped (to the waist) top will give a really retro look while tucking in a simple camisole and pairing it with sandals is a quick and easy evening look for warmer evenings. 

As bootcuts are heavily influenced by the '90s, there are plenty of low-waisted iterations. Get around the low waistband by pairing your jeans with longer-line tops, or bodies that will give plenty of coverage. Just make sure to keep long tops or bodies slim fitting. Play with different lengths and team with a cropped jacket or cardigan for a stylish layered look that will highlight your waistline.

5. How to style bootcut jeans under a dress

With the love for all things Y2K continuing, it's time to grab your jeans and pair them with your favourite dress. How to style skirts over trousers, or in this case dresses over jeans made a big impression on the runway, so try and banish images of Noughties halterneck and asymmetric hems over low-slung bootcuts though - in 2023 this pairing has gone seriously stylish.

First up, go for longer lengths. While back in the day mini and above-knee dresses were the way forward, midi (and even maxi) dresses work better in this modern variation. Your jeans should be secondary to the dress, but if you do want to show them off more, choose a high-low hemline or a dress with thigh-high splits.

A great transitional look for autumn, to ensure this look isn’t too bulky, choose slim-fit bootcut jeans so you’re not carrying too much volume around your thighs and waist.

6. How to style bootcut jeans for petites

When it comes to the best petite jeans in a bootcut style, Sam says it’s all about getting the right leg length and rise.

“The inseam or leg length is important to get right when you are 5'2" and under,” she says. “Look for denim brands and retailers that offer a selection of leg lengths. Abercrombie & Fitch, Hollister, M&S, River Island & Karen Millen are good for offering different leg lengths.”

She continues: “Another thing to look at is the height of the front rise, make sure it’s just an inch under or on your belly button to look in proportion.”

All the same rules apply for petite figures in that it’s best to team bootcut legs with less volume on the top. Sam also recommends a heel, as this will have the illusion of making you look immediately taller.

“Where possible, wear higher-heeled boots or shoes to elongate your petite frame,” she advises. ‘If the bootcut fits fabulously but is too long, get them professionally shortened, otherwise, you'll be tripping over your hem!"

7. How to style bootcut jeans for plus size

Sam believes the most important element of bootcut jeans for plus size figures is the fabric. 

“Check the label to see exactly what the jean is made from,” she says. “Plus size women should look at the fabric content and the amount of stretch and recovery a jean has specifically for comfort and wear and tear of the garment.”

She advises that while polyester will give the jean the ability to snap back into shape, also look out for lycra, spandex or elastane, which will help your jeans fit you better and give more comfort, making them the best jeans for curvy women.

“The higher the percentage, the stretchier the jean will feel on,” she says.

Proportion still plays an important roll here and you'll want to highlight your waist if you're looking to create an hourglass silhouette, so tucking or half-tucking tops into high-rise jeans is a great idea. Stretchier denim will also help to eliminate waist gap at the back of your jeans.

Are bootcut jeans back in style for 2023?

Lesley Torson, founder of Trilogy, believes that the bootcut is now back for good on the denim scene.

“Catching up with the straight leg is a classic bootcut jean, which is again growing in dominance and popularity,” she says.

“An extremely leg-lengthening fit, the bootcut is offered in shorter lengths such as Mother’s Weekender Jean, making bootcut and flared styles work for all heights of customers. Cropped bootcut styles are also great with trainers or flats for relaxed, day-to-day wear through the warmer months. For dressing up, a style like Citizens of Humanity’s Lilah jeans looks great with a heel.”

Where should bootcut jeans fall?

Bootcut jeans can be a bit tricky to get right lengthwise. If they don’t fall quite right, they can end up making you look a bit awkward, a bit like you’re wearing jeans you’ve grown out of. 

Sam says there are two lengths of bootcut jeans that you should consider, starting with a longer, full-length bootcut jean.

“A full length bootcut jean gives a fabulous, elongated silhouette and should be worn ideally with heels for that sexy svelte style,” she says. “Keep them long with the hem hitting just before the base of the toe (1-inch from the floor). If there's a break in the long line of the leg, the length is too long.”

Alternatively, you can go for something more cropped.

“The crop boot cut can fall (depending on your height) just above the ankle or below the calf,” says Sam.

“Let your ankle boot be your guide as you may not want to show a bare leg in the colder months. The crop boot cut is such a great style for all season and works with all styles of footwear, ankle boots, trainers, flats and heels, plus it gives the illusion of a longer leg too.”

Can I wear bootcut jeans with sneakers?

While bootcut jeans have traditionally always been teamed with some sort of heel, Sam says don’t discount flats as they work just as well - it’s all about choosing the right style of bootcut jean.

“Bootcuts look timeless with white trainers, so choose a pair of jeans with a shorter leg length for flats and trainers,” she advises. “If two pairs of bootcuts feel excessive, look for a pair with a split vent in the hem so you can wear them with both a trainer and a mid-height heel.”

Which type of tops look good with bootcut jeans?

The key to how to style bootcut jeans with any type of top is to think about balancing out the shapes of your outfit. A bootcut jean naturally flares at the hem of the jean, that means that through the rest of your silhouette, at least until the shoulder area, you want to keep your look relatively streamlined. By keeping volume balanced to the hem of the jeans and the shoulder area of a top, you naturally create the illusion of a narrowed waistline and this shape will help highlight your waist, instead of losing your figure under swathes of fabric. This can be achieved by tucking in more floaty silhouettes, if you don't want a fitted jersey top. 

If you do want to add volume, look to shoulder details that draw the eye up. A wider neckline - such as a boat neck, or an asymmetrical neckline or ruffle detail balances the width you have created at the hem of the jeans.

Are bootcut jeans flattering?

Bootcuts haven't always been given the fairest of fashion deals, and are a style of jeans that has drifted in and out of fashion over the last decade. As with a flare, the wider hemline can be tricky to navigate, but a bootcut only kicks out a little, making them universally acceptable. 

Bootcut jeans can be extremely flattering - regardless of body type, but it's all about nailing how to style them that will help you create the silhouette you desire. For a more narrowed waistline, remember not to hide your middle, tucking, or half tucking your top in, to create a distinctly cinched in look that will help balance the wider jean hem. This is true of your top choice too. Opt for a design with shoulder ruffles, or a blazer that has a strong shoulder line to reflect the hem of your jeans.