"As if finding the perfect jeans isn’t complicated enough, the real challenge often comes later in the getting-dressed process: deciding which shoes to pair with your jeans. Back when denim trends used to be a little more long-lasting—like the near-decade we shimmied into skinny jeans every morning—the answer was a little more clear. But odds are you now have a whole slew of denim styles in your closet that you alternate between, and figuring out which shoes pair best with them can feel like a make-or-break choice every single morning.
Your jeans are meant to be one of the most versatile parts of your wardrobe, and the key to that flexiblity is how you style them. From barrel-legged jeans to your tried-and-true skinnies, these are the best shoes to pair with your favorite denim styles.
Skinny Jeans
Whether you never deviated from your favorite skinny jeans or are giving them another go-around after recently seeing them on Alix Earle and Taylor Swift, one of the best parts about skinny jeans is the wide variety of shoes you can pair with them. While you might have kept yours around for the sake of tucking them into your knee-high boots, these three shoes are a great match for skinny jeans.
Ballet Flats
While the return of skinny jeans came as a surprise, an even bigger surprise might have been the return of their long-time accomplice: ballet flats. To make the duo feel a little more 2025 rather than straight out of 2004, balance the slimmer silhouettes on your bottom-half with a top and jacket that are more oversized.
Knee-High Boots
When skinny jeans went out of style, it felt as if knee-high boots did too, as their styling felt limited to being exclusively paired with skirts and dresses. Fear not, though: You still can—and should!—pair your skinny jeans with knee-high boots. To make the combination feel modern, I’d pair the duo with a slim-fit turtleneck and oversized blazer on top.
Ankle Boots
Rather than reaching for lug-soled, chunky boots, pairing a slim ankle boot with your skinny jeans can make your look feel totally streamlined (and your legs feel a mile long). With this combination, I like to think of the bottom-half as a base, rather than the focal point of the outfit. Allow this jeans-and-shoes combo to serve as a sleek backdrop to a top, outerwear, and shoes that stand out.
Straight-Leg Jeans
Despite straight-leg jeans feeling like the default denim style, they can feel especially tricky to pair with shoes. Assuming that your straight jeans are full-length, slim sneakers, ankle boots, and kitten heels are foolproof pairings.
Slim Sneakers
A low-profile sneaker is the perfect companion for any straight pair of denim, especially ones that are a bit more fitted throughout the leg. Not only does the slimmer shoe silhouette help to lengthen the leg, it also helps to prevent the hem of the jean from pooling around the ankle—a result that’s likely to form with a chunkier sneaker.
Ankle Boots
When choosing boots to pair with straight-leg jeans, the key is ensuring that your boot’s shaft is high enough to fit completely under the hem of your jeans. When the shaft is too short, it can create a gap of skin between where your jeans end and shoes start, which creates a break in your outfit that’ll make it feel less polished. If your jeans’ inseam hits near the top of your foot, opt for a pair of chunky, lug-soled boots; if they’re on the longer side, a pointed-toe, heeled boot will give an especially chic effect.
Kitten Heels
With a pair of straight-leg jeans, a kitten heel’s understated design can create a base that’s easy to pair with just about anything—a sweater, tee, blazer, you name it. The lower heel adds juuust enough height without overpowering the relaxed effect of the straight jeans.
Baggy Jeans
As a stylist, one of the questions I get asked most is which shoes are best to wear with baggy jeans. Though baggy jeans are completely effortless in theory, their bulkier shape can quickly feel too bulky when paired with the wrong pair of shoes.
Block-Heeled Boots
The beauty of baggy jeans is that there’s an extra bit of room to spare throughout the length of the pants—and most importantly, extra fabric to keep you from worrying about precisely where the hem is hitting. A block-heeled boot will keeps the jeans from swallowing your feet, unlike a thinner heel that could get lost in the bulk.
Pointed Pumps
Contrary to popular belief, baggy jeans can be dressed up just as easily as slimmer denim silhouettes. A pointed pump will perfectly juxtapose the relaxed vibe of your jeans for an It-girl effect that you’ll want to turn back to again and again.
Knee-High Boots
Looking for new ways to style your knee-high boots? Try wearing them underneath your baggy jeans. The wide width of the jeans will ensure they can drape over the height of your boots without feeling uncomfortable or restricting, and will also avoid having to execute the perfect tuck that slimmer denim fits would require.
Barrel Jeans
While barrel jeans’ more exaggerated style gained their fair share of controversy last year, the horseshoe-shaped style isn’t going anywhere in 2025—and is actually far more wearable than you might assume.
Heeled Boots
Since barrel jeans have a more exagerrated silhouette, a slim, heeled boot will help to keep the continuation of the curved leg going while balancing out the proportions of the more structured shape.
Chunky Mules
The weightiness of a chunky pair of mules that begin directly at the hem of your barrel jeans will create a harmonious look that pairs easily with any top, jacket, or outerwear.
Platform Loafers
Rather than a slender pair of loafers (think: the Gucci Horsebit Loafers), a pair of platform loafers will help you to avoid the too-narrow effect that a slim pair of shoes might create when paired with barrel jeans.
Wide-Leg Jeans
The shoes you pair with your wide-leg jeans will depend on their length. If you’re rocking a pair that allows you to wear flat shoes, opt for a pair with a bit of substance; if the inseam is on the longer side, opt for a heeled boot with a slim silhouette. Remember: It’s all about balance.
Chunky Sneakers
If you’re pairing your wide-leg jeans with an oversized top, opt for a slim pair of sneakers, like Gazelles or Sambas; however, if you’re going for a fitted top, chunkier sneakers are your best bet.
Heeled Boots
A pair of wide-leg jeans styled with heeled boots is the duo that’ll never go out of style. The combination feels instantly put-together, and will deliver a leg-lengthening illusion that those on the shorter side will especially benefit from.
Western Boots
Western boots—especially ones with a taller shaft and pointed toe—perfectly compliment the relaxed feel of wide-leg jeans.
Cropped Jeans
Regardless of the style of your cropped jeans, choosing footwear that doesn’t enhance the gap between the hem of the pants and top of the shoe will help to create an intentionally styled look every single time you wear them.
Penny Loafers
Since cropped jeans already highlight a good portion of skin, loafers further emphasize the shorter inseam by offering a subtle peek of skin across the top of your foot, creating a balanced and intentional look.
Ballet Flats
When picking shoes to pair with cropped jeans, I like to opt for pairs that either completely expose my ankle, or completely cover it up. Either extreme will help to make your look feel intentional from head to toe.
Tall Ankle Boots
If you want to pair your cropped jeans with a pair of boots, be sure to opt for a pair with a taller shaft. (Again, an awkard gap of skin showing can look sloppy and disjointed.) A boot with a tight, slim shaft will help to create a chic juxtaposition to any wide, cropped jeans.
Tinsley Crisp, Fashion & Beauty Staff Writer
Tinsley Crisp is a Fashion & Beauty Staff Writer at The Everygirl and specializes in reporting on the season’s latest trends and hottest products. As a New York City-based stylist, she’s committed to injecting joy into the art of getting dressed and delivering attainable yet aspirational content to our readers.
Madeline Galassi, Senior Fashion & Beauty Editor
Madeline Galassi is the Fashion & Beauty Editor at The Everygirl, where she oversees the fashion and beauty categories of the site. She brainstorms, writes, and edits stories across a broad range of topics including trend reports, product reviews, celebrity style, and more. She’s always keeping a pulse on the latest trends to create timely, exciting content for our readers.