Finding the right winter boots is no easy task. Especially when jean trends have changed so much. These are not the easy breezy days of the skinny jean, where tall boots were slipped on with ease and short boots were paired with an appropriately cuffed ankle. Now, with baggy jeans and 90’s cuts running rampant, it can feel a lot more difficult to be on trend, particularly when it comes to boots.
Don’t fear, though, a lot of us are feeling lost in this new climate, and that’s okay. As a millennial, I’m absolutely an advocate of cramming jeans into your boots any old way, just like we shoved our bootcut jeans into our tall Uggs once upon a time. Whether or not you’re down with that approach, here are some trending boot styles for winter 2025 you need to look out for.
Rock a riding boot
What’s more posh and sophisticated than a sleek riding boot? In terms of winter fashion, almost nothing. A riding boot can help create a distinct old money vibe, or it can add a touch of polish to an eclectic outfit. Beyond their easy sophistication, their low heel adds some practicality.
Show up in slouch boots
Swashbuckling, slouchy boots not only bring an adventurous boho vibe to your wardrobe, but they’re also super trendy at the moment. They may remind some of Captain Jack Sparrow, but in reality, they can add a sumptuous touch to a simple outfit.
These pair well with a traditional skinny jean, but they’re also great for those that like to wear straight leg or boot cut jeans. You can easily stuff your pantlegs into them, and create an on-trend and edgy look. A long or mid length skirt is also a great idea with these boots.
Go out on the town in western boots
Whether you like it or not, western-inspired trends are here, and they’re likely going to hang out for a moment. You may not be into cowboy hats or cowprint accessories, but western boots are a great way to incorporate this trend into your outfits without going over the top. It’s also another way to add some Y2K charm to your winter look. A dark brown, black or tan boot is great for a low-key approach, but if you really want to have fun, opting for boots with studded designs and rhinestones can truly unleash your inner cold-weather cow girl.
Look sleek in sock boots
Fitted boots, or sock boots, are another trend you need to try in Winter 2025. These boots are ultra-sleek and elegant. They can be paired with anything, but you may get the most impact by rocking them with a mini skirt and tights or a super thin legging underneath, especially if you’re wearing a tall sock boot. Shorter sock boots, on the other hand, work amazingly with 90s cut jeans and other baggy or boot cut styles.
Relive a Y2K trend with sheepskin boots
Sheepskin boots, or Uggs, are back in style, with a caveat. While the 2000s shoe staple has made a comeback, Gen Z is not reaching for the mid-calf styles of the past. Rather, lower-profile boots are what’s in. The ultra-low boot silhouette is a safe choice. However, if you truly want to be trendy, opting for Ugg slippers is the way to go. What’s great about these is not only that they’re comfortable, but they pair easily with a baggy pant. Bonus points if you opt for platform boots, which, in addition to being in style, also help keep your pants from dragging on the ground and getting wet. Sometimes fashion can be practical!

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