How to Wear Bootcut Jeans Without Going Retro

The battle between the most debated styles of denim—skinny and Bootcut Jeans—is quite fierce. Much to the dismay of those who recall wearing them in their heyday, both silhouettes are in vogue again, driven by key pop culture moments and the endless cycle of decade-inspired trends. So, are bootcut jeans in style? While we might manage to hold off the widespread return of skinny jeans for a bit longer, it's clear that bootcuts have firmly reestablished their place in the fashion scene.

What are bootcut jeans, and why do they keep popping up in fashion? With a rich history that spans '70s hippie culture, classic '90s hip-hop, and memorable Y2K red carpet appearances, bootcut jeans have certainly had their ups and downs. If you find yourself intrigued by the look but unsure about styling flare jeans, you're not alone. Fortunately, we’re here to help! Below, you’ll find modern bootcut jeans outfit ideas for women that cater to a variety of tastes and styles.

With a sweater

Skip the chunky knits and opt for a cropped, boxy, or smart sweater instead. Consider modern high-waisted bootcut jeans for a contemporary look. If your sweater is too long, do a French tuck or cinch it with a belt to create a more defined waistline.

We went for a sleek pair of High-rise bootcut jeans from Citizens of Humanity and styled them with the Poloneck sweater from Lisa Yang and heeled boots. The resulting look has a demure vibe that's ideal if you're intrigued by this retro silhouette but wary of resembling a past era too closely.

With a blazer

What to wear with bootcut jeans for a business casual look? Can they actually go business casual at all? Bootcuts are a universal style that is easy to dress up with a blazer for a smart appeal. A fitted blazer works best, as it highlights the waist and maintains a sleek silhouette; however, opt for a cropped jacket for a more modern and playful vibe.

​We love a blazer that looks as though it’s not left the library for decades, like the Corduroy single-breasted blazer from House of Dagmar. Even more so when worn with the High-rise bootcut jeans. Put the Relaxed-fit roundneck pullover from FTC Cashmere underneath to complete the pure vintage aesthetic.

With a top

To achieve a model-off-duty look, combine your bold statement pieces with more understated items that add a touch of edge—a fitted off-the-shoulder top or a trendy tube top can help you with that. This approach also makes a strong case for giving bootcut jeans the same stylish recognition.

The Rouched tube top from House of Dagmar is on our list of the best tops to wear with flare jeans. Keep it fancy with a pair of navy High-rise bootcut jeans and finish the look with kitten heels and minimalist accessories.

Double denim

Choose denim shirts to wear with flare jeans if you can't get enough of Y2K or are looking for some denim-on-denim for your Western tour. A Canadian tuxedo is a classic pairing that never fails to make a statement. Opt for black pointed-toe shoes, then accessorize as you please—mixed-metal jewelry or an array of bag charms would be a delight.

This outfit brings together Western-inspired style with British notes for a classic look that can be leaned on time and time again—just pair the Denim oversized shirt with the High-rise bootcut jeans. Add in some sleek accessories—a clutch and sunglasses will do the trick—to keep the look modern.

With a jacket

There's an ongoing fascination with 2000s fashion, especially with items like bootcut jeans, as well as utility and field jackets. European style stands out for its unique flair, often leading the way in blending vintage pieces with oversized silhouettes and a range of diverse influences.

This outfit is the perfect rephrasing of cool city girl dressing, layering the Field cotton jacket from House of Dagmar over the Ribbed knit top from Tiger of Sweden, the High-rise bootcut jeans, and square-toe leather shoes.

With a coat

Keep an eye on balance and proportion in this combo. Since bootcut jeans have a wide leg, you'll want to choose coats that complement that silhouette, not overwhelm it. The good news—most coats look great with this style. Cropped jackets, bombers, and hip-length styles work well and create a balanced look. However, long coats also work; just select styles with structure and avoid too boxy pieces. 

You can absolutely have a low-key day out and rock an outfit with a vision. Pair your High-rise bootcut jeans with the Oversize doublé coat from House of Dagmar and the Highneck cashmere sweater from Lisa Yang, and you have an instant look to embody main character energy at the market or bookstore.

With a blouse

There’s something about wearing jeans with a blouse that gives off a creative professional vibe, especially if the blouse is a bit oversized and the jeans are flared. Pair it up with a belt, a cute woven handbag, and stylish heels, and you’re all set to head from the office or gallery to meetings around town.

The power of structure and silhouette in transforming a seemingly simple outfit into inspired territory is truly significant. When the jeans are the High-rise bootcut jeans accompanied by the Asymmetric cotton blouse by Erika Cavallini, and the bag has an interesting shape, you truly can take on the world.

With boots

What are the best shoes to wear with bootcut jeans? Actually, these are the jeans that were literally made for boots—check out the name! Debuting in 1969, their subtle flare at the hem quickly won over cowboys and rodeo riders for their practicality. The design allows boots to fit smoothly underneath, creating a seamless look from hip to heel. 

So, we know bootcut jeans with boots do work, but what style is the best? Bootcut jeans are the perfect length for ankle boots, such as the Ankle leather boots from Voile Blanche, deliberately designed to show off the ankle and elongate your silhouette. Having a slight platform also works well, especially if you’ve gone for the longer-length floor-skimming bootcut to give you those legs that go on for days. Check out the classy Leather Chelsea boots for that forever-in-style look.

With sneakers

While bootcut jeans' initial purpose, surely, was to fit over heeled boots, you can use the silhouette to show off any statement shoe you like. Don’t discount flats, as they work just as well—it’s all about choosing the right style of bootcut jean. Is it possible to pair this jean style with sneaks? And if it is, how to wear bootcut jeans with sneakers? Bootcuts look timeless with minimalist sneakers, so choose a pair of jeans with a shorter leg length for flats and trainers. 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 sneaker and a heel.

The white Textured-trim leather sneakers from Ghoud are an understated basic that will work with everything, even—bootcuts. The Fur-lining wool sneakers from Voile Blanche are a seasonal addition that will allow you to nail the look in the winter as well.