I Did the Research: Celebs Almost Always Style Their Bootcut Jeans With These Shoes

Shoes are one of the most important pieces in any look—and nowhere is that more evident than outfits with bootcut jeans. Lately, celebrities have been proving that the easiest way to make bootcut denim feel elevated is by pairing it with pointed-toe boots. And I’m next in line to give this pairing a try.

As skinny jeans continue their slow fade (sorry, millennials), relaxed yet still streamlined denim silhouettes like bootcut have stepped into the spotlight. But styling them can feel a little tricky. Bootcut jeans aren’t wide, yet they’re not straight either—which is why footwear matters so much. The slight flare looks best when anchored by shoes that add just the right amount of height and definition. Enter heeled, pointed-toe boots that peek out just enough from under the hem, a celebrity go-to that feels both effortless and intentional.

Ahead, we’re breaking down not just the best boots to wear with bootcut jeans but also other shoe styles that pair just as well—so you have options for every mood, season, and outfit formula.

The Style Celebs Choose Again and Again: Pointed-Toe Boots

All it took to upgrade this jeans and T-shirt look was a good pair of pointed-toe boots and a leather trench coat. Try this at home.

Taylor Hill made this frilly blouse look extremely elevated while pairing it with jeans. I'd like to thank the boots for that.

Anything Margot Robbie wears immediately sends me to some sort of checkout cart. Luckily, this is a look I can re-create at home with what I already have (and you probably can too). Just pick out your favorite oversize blazer.

A matching set looks even better when it comes in denim. The pointed-toe boots just might be the perfect finishing touch.

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More Shoes to Style With Bootcut Jeans

1. Chelsea Boot

You can't go wrong styling bootcut jeans with a classic pair of Chelsea boots. The ankle height of the shoe sits perfectly underneath the flared edge of the jeans, ensuring they don't create that unappealing scrunched-up look.

2. Heeled Ankle Boots

For bootcut jeans with longer hemlines, opt for footwear that will give you a bit of height—like heeled booties. During colder months, a heeled ankle boot will transition these jeans into the season and keep your denim from dragging on the ground, which is a win-win in our books.

3. Chunky Loafers

With bootcut jeans, the flare can range from '70s-inspired to slightly more minimal. If your pair falls in the latter category, it's easier to get away with styling them with flats as the hemline won't drag on the ground. But to be safe, with flats, you want to opt for a style that will still give you a little lift, like a pair of chunky loafers.

4. Platform Sneakers

Another flat footwear option you can rely upon to look good with semi-flared denim? Platform sneakers. The chunkier silhouette will keep your pants from dragging while also dramatizing the relaxed silhouette.

5. Ballet Flats

Unless you just bought a brand-new pair of jeans, chances are you've worn them in quite a bit. Rather than ditching a pair of bootcut jeans that have maybe shrunk or frayed over time, consider embracing the more relaxed look by pairing them with ballet flats. By doing this, you'll give the jeans a baggier appearance, which is trending at the moment. Plus, you'll get more wear out of them!

6. Heeled Mules

Let's be honest: We might love flats, but they don't always work with bootcut jeans. Whether the fit of your denim doesn't work with flat shoes or you're dressing for a more formal occasion, you want to have a foolproof footwear option to turn to when styling these pants. Enter heeled mules. No other footwear can elevate this denim (in every definition of the word) like these shoes can.

7. Cowboy Boots

Since bootcut jeans have been considered a Western-inspired silhouette for decades, it doesn't hurt to lean into the history of this type of denim by pairing it with cowboy boots. While the idea might seem a bit too on-theme, the truth is that many fashion people regularly pair these jeans with this footwear. The key to pulling it off is pairing your flared denim with an ankle cowboy boot that feels contemporary so that it doesn't feel cliché.

8. Slingback Heels

If you're not a fan of Western-inspired footwear, there's another style you can rely upon to give this "dated" denim a contemporary touch: slingback heels. Although this type of footwear has been around forever, with so many modern iterations on the market, it makes them the perfect item to pair with these jeans.

9. Winter Boots

Although bootcut jeans are a staple that can be worn year-round, it can be a bit more challenging to style them during colder months as one might be worried about the hemline dragging in the snow. Rather than packing away these pants until the springtime, try pairing them with winter boots. Not only will opting for this footwear allow you to navigate winter storms with ease, but its height allows it to be comfortably worn underneath the flare of your jeans without having to tuck them in.

10. Strappy Sandals

Hopefully, you've got ample inspiration on what footwear to wear with your bootcut jeans by now. But if you need one last suggestion, let us leave you with this: strappy sandals. By pairing bootcut jeans with this footwear, you'll be able to show off your favorite open-toed shoes and prove once and for all that bootcut jeans are the only denim silhouette that matters.