3 Boots Not To Wear With Bootcut Jeans (Trust Us, Not All Boots Are Created Equal)

One of the fall 2025 denim trends you'll want in your closet is a pair of bootcut jeans, and we're so glad this silhouette is back. They elongate your legs while giving your bod some shape with the hip-hugging waist and a slight flare on the bottom. Bootcut jeans are also super easy to style, and we can't forget the shoes the jeans were named for — boots. Originally designed for cowboys so that they could wear their boots and jeans together, the style eventually became popular among non-ranching folks. However, while the flared hem allows for most shoes to be worn tucked inside the legs, not all styles pair well with bootcut jeans.

During spring and summer, it's so easy to pull on a pair of low-profile sneakers or some cute sandals with your bootcut jeans, but during the colder months, footwear becomes trickier. You can get away with wearing super chunky shoes with wide-leg pants, but bootcut jeans require sleeker shapes to keep with the lean aesthetic.

Because bootcut jeans are meant to look sleek, wearing anything chunky on your feet will impede the lengthening effect. Fashion stylist Liz Teich stated on Instagram, "Obviously, boots go with bootcut jeans, but make sure they're not round toe or heavy. And with any shoes, from boots to loafers, make sure they have an elongated toe." As Teich demonstrated how bootcut jeans look with a chunky, round-toed boot, it was clear that her legs looked shorter, and the hem of the pants bunched up in an unflattering way.

One style that has rounded toes is combat boots, which is an outdated boot trend to step away from for fall and winter 2025, so tuck yours away for the time being. Chelsea boots are more versatile, but choose one with a pointier toe rather than the clunky styles. If you don't like pointy toes, square shapes are also a good option. Just remember, a bit of height is optimal, so even if you choose a one-inch heel, that'll make all the difference in giving you that lengthened look.

Now's the time to say goodbye to your ankle boots this fall and walk into a fresher shoe trend. Knee-high boots with wider shafts are having their moment this year, and they look amazing over skinny jeans or paired with a cozy wool skirt. However, when wearing them under bootcut jeans, you'll likely see the outline of the shaft and create a ballooning effect on the legs. Although super-tight knee-high boots are outdated right now, that's the style you want to pair with bootcut jeans if you want to be extra warm in the winter.

Tucking your bootcut jeans into your knee-high boots will also look unflattering, as the fabric will bunch up around your knees and thighs. Save your wider boots for your other 'fits where you want to showcase them, instead of tucking them into your denim. This especially goes for bootcut jeans with a very slight flare or more of a straight leg, which won't allow for a lot of extra room.

If you live in a climate with a lot of rain or harsh winters, weatherproof shoes are a necessity. We get that it's impractical to trudge through the slush in cute suede booties, but when slipping on your snow shoes, leave your bootcut jeans safely tucked away in your closet. While there's fashionable winter footwear out there, they're still made to be sturdy and slip-resistant, so most of them will have a chunky rubber sole and rounded toes. Weather-proof shoes will also have a bulky shaft, particularly if they're lined with fleece. And, don't even attempt to pull your bootcut jeans over rain boots, as it'll be next to impossible.

Save this denim style for clear weather, as you want to be able to wear the appropriate footwear. Bootcut legs also tend to be on the longer side, and you won't want to drag the hemline in mud or snow. This particular style is made to look elegant and slimming, so we think it's best to stick with shoes that match their energy.