Bootcut jeans are officially having their comeback moment and we’re totally here for it. Whether you’re calling it the Kendrick effect or just the cyclical magic of Y2K fashion, one thing’s for sure: skinny jeans are taking a backseat, and bootcut is back in the style conversation.
These jeans hit that sweet spot between structured and easygoing, offering a refined silhouette with just enough flare to keep things interesting. They’re not too tight, not too loose, basically the Goldilocks of denim.
What makes bootcut jeans so special is that understated flare at the hem. It adds a touch of polish without feeling too dressed up, which means you can wear them for everything from coffee runs to dinner dates. But unlike skinny jeans that go with almost any shoe, bootcut styles need a bit more thought in the footwear department.
Because the hem typically skims the tops of your shoes, the right pair can completely change the vibe of your outfit.
In this post, I’ll be breaking down the best shoes to wear with bootcut jeans so you can style them like a pro.
Let’s go!
11 Shoes to Wear with Bootcut Jeans
1. Sneakers
Since bootcut hems flare slightly, opt for low-profile sneakers like classic white kicks or retro runners to keep the look clean and casual. Make sure the jeans hit just above the ground, no dragging!
For a laid-back vibe, pair them with a tucked-in tee or cropped hoodie. Want something more polished? Try a fitted blazer over a graphic tee.
2. With Pumps
Bootcut jeans and pumps are a match made in fashion heaven. The slight flare of the jeans naturally draws attention to your shoes, and pumps add just the right touch of elegance.
They elongate your legs, especially when the hem of your bootcut jeans gently skims the top of the pump without bunching.
This pairing creates a sleek, lengthened silhouette that works beautifully for both office looks and nights out.
3. Block-heeled Boots
Bootcut jeans and block-heeled boots are a stylish, practical pairing that just works. The structured shape of block heels balances out the flare of bootcut jeans, creating a cohesive silhouette that feels modern yet effortless.
Plus, the extra height helps prevent the hem from dragging, especially if your jeans are on the longer side. This combo is perfect for cooler months, just add a cozy sweater or tailored coat. Whether you’re going for a chic daytime look or something a bit more dressed up, block-heeled boots bring both comfort and edge to your bootcut denim ensemble.
4. Chelsea boots
Chelsea boots and bootcut jeans are a timeless combo that blends edge with everyday ease. The sleek, close-fitting design of Chelsea boots contrasts nicely with the subtle flare of bootcut jeans, making your outfit look effortlessly put-together.
Since Chelsea boots usually have a slight heel and hit at the ankle, they provide just enough lift to keep your jeans from dragging while still feeling super wearable.
For a sharp finish, make sure your jeans are long enough to skim the top of the boots without bunching. This pairing works great for transitional weather and adds a touch of cool to any outfit.
5. Heeled Sandals
Heeled sandals and bootcut jeans make a stylishly breezy duo, especially in warmer months. The open design of the sandals adds a light, feminine touch that contrasts beautifully with the structured shape of bootcut denim.
The heel gives you that extra lift, helping to elongate your legs and keep the hem from dragging. It’s the perfect mix of relaxed and refined—ideal for brunch, casual dates, or summer outings. Choose strappy styles or minimalist heels for a sleek finish and let the flare of the jeans subtly highlight your footwear. It’s an effortlessly chic way to dress up denim.
6. Chunky Loafers
Chunky loafers and bootcut jeans strike the perfect balance between polished and edgy. The bold, structured shape of the loafers adds weight to the bottom of your outfit, which pairs well with the slight flare of bootcut jeans.
This combo creates a grounded, fashion-forward look that’s ideal for fall or transitional weather. Go for cropped or slightly shorter bootcut styles to show off the loafers and avoid bunching at the hem.
7. Ballet Flats
Ballet flats and bootcut jeans make for a classic, effortlessly chic pairing. The soft, feminine shape of ballet flats contrasts nicely with the structured flare of bootcut denim, creating a look that’s both polished and relaxed.
Since ballet flats have a low profile, they work best with bootcut jeans that are tailored to hit right at or just above the top of the foot—no dragging allowed. This combo is perfect for a casual day out, a lunch date, or even a comfy work outfit.
8. Platform Sneakers
Platform sneakers and bootcut jeans are a fun, fashion-forward combo that adds height without sacrificing comfort. The chunky sole of platform sneakers complements the flare of the jeans, giving the overall look a cool, elevated edge.
Plus, the added height helps keep your hem from dragging while creating a longer leg line. This pairing leans into a retro, street-style vibe, perfect for casual days, travel, or running errands with flair. Go for bold or colorful platforms to make a statement, or keep it clean with classic white styles. Pair with a cropped jacket or fitted tee to balance the proportions.
9. Slides
Slides and bootcut jeans make for an easygoing, off-duty look that’s all about relaxed style. The open, slip-on design of slides gives your outfit an effortlessly casual vibe, perfect for warm-weather days or quick errands.
Since slides are flat, it’s best to wear bootcut jeans with a slightly cropped or tailored hem to avoid dragging. Think light-wash denim, a breezy tank, and your favorite slides for that effortlessly cool aesthetic.
10. Heeled mules
Heeled mules and bootcut jeans create a chic and modern pairing that’s perfect for elevating your everyday look. The open back and sleek heel of mules add a touch of sophistication while keeping things effortless. Because bootcut jeans have that subtle flare, they naturally draw attention to your footwear, making heeled mules the perfect way to show off some style and height.
This combo elongates your legs and adds a polished finish without feeling too formal. Pair with a flowy blouse or tailored blazer for a stylish outfit that’s ready for brunch, work, or a night out.
11. Cowboy Boots
Cowboy boots and bootcut jeans are a match made in Western-inspired style heaven. The natural flare of bootcut jeans perfectly complements the classic shape of cowboy boots, allowing the boots to peek out just enough for that iconic, effortlessly cool vibe.
This pairing celebrates both comfort and rugged charm, ideal for casual days, festivals, or when you want to channel a bit of country flair. Go for jeans that hit right at the top of the boots to avoid bunching and balance the look with a simple tee or denim jacket. It’s a timeless combo that never goes out of style.
Conclusion
I hope this was helpful.
Also check out my previous post on shoes to wear with a sweater dress.
Don’t forget to share with your family and friends via social media.
See you in the next one,
Yours stylishly!
