With so many denim styles trending right now, it can be tricky to figure out which shoes pair best with each one. A few years ago, I wrote a post breaking down what shoes to wear with different types of jeans, and since denim silhouettes have shifted quite a bit, I thought it was time for an update for Fall/Winter 2025. I also put together a new visual guide to make it easy to reference.
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If you’ve been wondering what shoes to wear with your jeans this season, this should help! It’s not an exhaustive list of every possible pairing, but it’s a great place to start. (Click here for a printable PDF.)
What Shoes to Wear With Straight Leg Jeans
similar trench // Quince cashmere tee (L) // MOTHER Dazzler (30) // VEJA Esplar (39) // Gucci Soho Disco
Straight-leg jeans come in lots of variations, from sleek and slim-fitting to more relaxed and slouchy—and they can be cropped, ankle-length, or full-length. Generally, we see two main versions: slim straight ankle jeans and full-length relaxed straights. Here’s how I like to style each.
Slim Straight Ankle Jeans
Slim straight ankle jeans are the modern alternative to skinnies—sleek and flattering, but with just enough room through the leg to feel current. They’re incredibly versatile and easy to dress up or down. My personal favorites are the AG Mari, MOTHER Dazzler, and Gap Factory Vintage Slim Jeans.
VEJA Esplar (39) // MOTHER Dazzler (29) // FRAME tee (XS)
They pair beautifully with loafers and loafer mules, ballet flats and Mary Janes, fashion sneakers (especially slim, low-profile styles like the VEJA Esplar or Dolce Vita Serina), clogs, and pumps. I especially love them with shoes that show a bit of the ankle—this keeps the line clean and elongates the leg.
Margaux The Demi Flat (8) // MOTHER Dazzler (30) // Michael Stars top (M) // London Fog trench (S)
Really, it’s hard to find a shoe that doesn’t work with this style, although ankle boots can be tricky. The best combo is a slender boot shaft that slips easily under the hem, as shown here.
Steve Madden Dorothea Bootie (8) // Gap Factory Slim Jeans (29) // Gap Factory stripe sweater (S) // AllSaints bag
Hint: You can read more about that in this post from last fall: How to Wear Ankle Boots with Straight Leg Jeans.
Avoid: Shoes that are too heavy through the sole can overwhelm the slim shape and break the line at the ankle.
The exception is a lug-sole boot—when the shaft is slim enough to tuck underneath (and the jeans don’t bunch on top), it can actually extend the silhouette and look really chic, as shown below.
Blondo Cammie Waterproof Bootie (8.5) // MOTHER Dazzler (30) // Rails Geneva Cardigan (S) // lululemon Rain Rebel (10)
Relaxed Straight Leg Jeans
Relaxed straight jeans have a slightly roomier fit through the leg and often hit at full length, creating an easy, trend-forward look. They’re a little more casual than the slim version but still very wearable for everyday. This isn’t a style I’ve really leaned into, but I did like the AGOLDE Lana when I tried them.
For a modern, effortless vibe, I’m seeing this style paired with low-profile sneakers or slim retro runners—they complement the relaxed shape without adding bulk.
AGOLDE Lana Straight Jeans (29) // Vintage Havana sneakers // old sweatshirt
They also work beautifully with classic loafers and boat shoes, and minimal flats like a slipper or Mary Jane can work too—but there’s something about a menswear-inspired loafer that seems to pair especially well with straight-leg jeans.
Ankle boots are another great option—just look for a slimmer silhouette to keep the line clean through the ankle and balance out the relaxed fit.
AGOLDE Lana Straight Jeans (29) // similar Marc Fisher boots (8) // old cardigan
Avoid: Ultra-chunky soles or wide, heavy boots can make the silhouette look bottom-heavy. A shoe that follows the line of your foot helps keep the proportions balanced.
What Shoes to Wear with Bootcut & Flare Jeans
MOTHER Fray Hem Flare Jeans (29) // similar Blondo boots (8) // similar navy sweater // PEI Shoulder Bag
Bootcut jeans and flares are pretty much interchangeable when it comes to shoe pairings, so I’ve grouped them together here—but there are some subtle differences worth noting.
Bootcut jeans are fitted through the hips and thighs, then gently flare out from the knee to the hem. The flare is usually slight—just enough to balance out the leg and make room for boots (hence the name).
Gap Factory Baby Bootcut Jeans (29) // Jeffrey Campbell booties (8) // black stripe sweater (S)
Flare jeans, on the other hand, are the more dramatic version. They fit straight through the hips and thighs, then widen out from the knee, often with leg openings wider than 20 inches. Flares tend to have a bit more attitude and can easily be dressed up or down depending on the wash and fabric.
Pistola Kinsley Flare (29) // similar rag & bone booties (39) // similar grey turtleneck // Rails jacket (S)
Like straight-leg and wide-leg styles, both come in cropped, ankle, and full-length versions, and I like to keep a mix in my closet. Bootcuts are great for an everyday classic look, while flares feel a little more statement-making and elongating.
Full Length Flares
Full-length flares give you that long, leggy look that’s so flattering and easy to dress up or down. Current favorites include the MOTHER Weekender and the FRAME Lax, a slightly relaxed flare that feels especially modern right now.
FRAME Lax Relaxed Flare (29) // similar boots // Michael Kors jacket (S) // Bevan top (S)
They tend to look best with heeled shoes, which help the hem skim the top of your foot and create that elongated line. Pointed-toe styles—whether boots or pumps—are especially flattering because they continue that long, lean shape. Platform shoes and clogs also work beautifully (especially when they’re trending), adding height and helping the flare drape just right.
MOTHER Weekender Flare (39) // pumps // old satin blouse
That said, I’ll occasionally wear my flares with sneakers for a more casual, laid-back vibe. When I do, I prefer sleek leather platform styles to keep the proportions balanced.
EVEREVE Camp Jacket (S) // FRAME tee (XS) (option) // MOTHER Weekender (29) // Paul Green sneakers (8) // similar belt // Yurman earrings // similar pendant // Goyard tote // AWAY The Medium
Avoid: Chunky loafers and boat shoes, rounded-toe shoes, or lug-sole boots that can look clunky and interrupt the smooth line of the flare.
What Shoes to Wear with Barrel-Leg Jeans
Barrel-leg jeans have been around for a few seasons now, and they’ve stuck around longer than I expected. Once considered more of a fashion-forward trend, they’re definitely becoming more mainstream.
This style has a curved, slightly sculptural shape—wider through the thigh and tapering toward the ankle—which gives it a distinctive, modern look. Getting the length right is key: barrel jeans tend to look best at ankle length, where a little skin shows between the hem and your shoe. That small gap helps keep the silhouette balanced and flattering.
MOTHER Half Pipe // Splendid Ruth Mary Jane (8) // LOFT wedge sweater (S)
I’ll be honest—I don’t love this style on me—but I’ve seen it look really chic on others when styled well. Barrel jeans pair nicely with sleek sneakers, retro runners, ballet flats, or Mary Janes.
If you prefer boots, there are a few ways to go. Chunky lug-sole Chelsea boots or platform styles can look really cute with barrel jeans—the extra weight at the bottom helps balance out the volume through the leg. You can also try a slimmer mid-shaft boot that’s tall enough for the hem to clear the back of the boot for a smoother line.
Avoid: Delicate shoes like strappy sandals or dainty heels, which can look out of proportion with the curved leg. For boots, skip styles that are too short or wide at the shaft—the hem can get caught and disrupt the line.
What Shoes to Wear With Skinny Jeans
PAIGE Gemma (29) // LOCI sneakers (8) // Andrew Marc Coat (S)
While skinny jeans aren’t the trend they once were, they’re still a wardrobe staple for many—especially in cold weather. Their slim fit makes them ideal for wearing with tall boots, knee-highs, or riding boots, and they also pair easily with Chelsea boots, pumps, sneakers, and flats.
If you’re updating your denim collection, you might try swapping them for a slim straight style for a slightly more modern look. It offers the same sleek silhouette, but with a little extra room through the leg that makes shoe pairing easier.
In Summary
It may feel like anything goes right now—and honestly, that’s not far from the truth. Almost any denim silhouette can look current if it’s styled in a modern way, and a lot of the traditional “style rules” are being challenged.
Gap Factory Barn Jacket // Gap Factory stripe sweater (S) // MOTHER Roller Sneak // boots? // Clare V Moyen Messenger
At the end of the day, it’s all about experimenting in your closet and finding the combinations that feel best on you. Hopefully this guide helps you narrow down your options and gives you a starting point for pairing your favorite jeans with the right shoes.d try on different combinations to see what works best for you, but hopefully this helps you narrow down your options.
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And if you want more style advice, see all my posts about 2025 Fall Shoe Trends!
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