When it comes to boots, I'll try just about any trend or style at least once. Between chunky Chelsea boots, lace-ups and quilted rain boots, I've yet to meet a style I don't like. Because I'm in the mood to pretty much exclusively wear boots right now and because the rainy, snowy (even muddy!) weather often requires them, I've styled five looks around my new favourite pairs from Sperry. No matter what type of weather I'm dressing for on any given day, I can rely on this brand for stylish footwear that will take on the elements. If you're ready to switch up your go-to cold-weather outfit or simply craving some fresh boot-styling inspo, you're in the right place.

No matter the season, I'm always going to gravitate towards black-and-white outfits. There are few color combos as chic, in my opinion. For this reason, I'm loving these black Sperry Chelsea boots with the chunky black sole. Plus, the rubber material means I can stomp through puddles and mud without ruining my shoes. I kept the majority of the apparel black with white details to keep things feeling elevated and to coordinate with the boots. Did I nail it, or did I nail it?

For an outfit that's a bit more elevated, I'm loving these heeled duck boots. They add a bit of polish to the outfit while still being perfect for a rainy day or night. I kept the rest of the outfit pretty neutral with an ivory sweaterdress, a plaid scarf and tan, leather accessories. Even if the forecast shows sunshine, I'd still wear this cute and cosy look.

I know everyone loves a good denim-and-boots outfit, and I aim to please. I wanted to keep things interesting, though, so instead of classic brown boots, I opted for this two-tone pair (which just so happens to be water-resistant, by the way). I like the idea of styling these with knits in a similar colour palette and then balancing it all out with polished, wide-leg jeans and a sleek shoulder bag for a look that feels casual yet sophisticated. The beanie is optional, but I'll be grateful to have it when it starts to snow.

These boots are ideal for when you need to wear weather-friendly footwear but don't want the look of traditional rain boots. The fact that these have an on-trend lug sole and are a slip-on style sold me. For a sporty vibe, I styled the boots with elastic-waist cargo pants, an oversized knit and a bag and zip-up jacket both made of nylon (because it's not just the boots that need to withstand the rain). Catch me in some version of this look—if not this exact one—on the weekends until further notice.

Duck boots are my go-to for rainy days, but this leather pair is next-level cool. I had to style them with a sherpa bucket hat and other cosy pieces like a knit dress and wool socks. Just don't forget an umbrella.

It doesn’t matter how old you are; as soon as summer is over and fall’s on its way, it’s hard not to feel nostalgic for back-to-school season. Stocking up on new bags, collecting supplies, and buying new clothes—specifically a first-day-of-school outfit—are all quintessential memories of starting class. Luckily, even if you’re not sitting in homeroom anymore, you can still take part and transition or update everything you have, just because you can. Where to start? Treating yourself to a few key essentials from Sperry, including a pair of comfortable and stylish shoes, which are not only practical but also extremely elevated, so you won’t be sacrificing comfort for style here.

Scroll down for four “back to fall” essentials from Sperry. 

Don’t let colder weather get in the way of wearing stylish shoes. Even though you have to be more covered up and it’s harder to get around town in crummy weather, there are options that are both comfortable and fun. Sperry has plenty of elevated picks—preppy vibes included—so you won’t feel like you’re sacrificing your outfit for comfort.

You don’t need to be a student to have a journal. In fact, having one with you at all times will not only keep you organised, but also help you remember all your ideas.

Fall and winter are all about layering, so having an assortment of shirts on hand is pretty much mandatory. You can never go wrong with a classic print, like stripes, or something neutral.

Everyone needs to own some sort of backpack. Whether you use it for travelling or toting your things around town, it’s necessary in the fall. You can throw pretty much everything in it without worrying that your valuables will be rained or snowed on.