
Crystal here from Team PMT with a roundup of our favorite winter boots (including water resistant boots for winter!). Whether the winter season where you live is more on the mild side, the cool and rainy side, or the freezing cold and snowy side, you want boots that not only keep your feet dry and your toes toasty, but also look stylish. This week’s Friday Finds is all about helping you find boots you’ll love wearing all winter long.
- Super Casual: Boots that work with sweatshirts, relaxed sweaters, jeans, and puffer jackets. These can be lug sole or all-weather boots. They are marked with “1” in the widget below.
- Nicer Casual: Boots that work with both relaxed and nicer sweaters, elevated casual tops, blouses, cardigans and blazers, and casual dresses. These are a bit sleeker than a lug sole boots, creating a sleeker look with elevated casual pieces like the ones I just named. These boots are marked with “2″ in the widget below.
- Dressy: Boots that sharpen up work looks and special occasion outfits. The kitten-heel style I included in the widget below works EVERY TIME. Make it your go-to option, and you won’t have to think about boots when you’re dressing for work or special events. The pointed toe adds sharpness to every single outfit, keeping you from looking frumpy or dowdy. The high shaft works well under all pants, and it looks great with dresses. The kitten heel looks intimidating, but if it’s low, it’s WAY easier to walk in than you think. These boots are marked with “3” in the widget below.
- I included a super affordable pair of dressy boots from Target (with GREAT reviews), and a pair of dressy boots from Madewell that you’d expect would be much higher quality. If you are uncertain if you really need this style of boot, go for the Target pair because I want you to have this as a fallback option in your wardrobe! You are gonna need it if you have to get dressed up for work or special occasions. They’ll make your outfits look right!
Need help figuring out just how to wear boots with various cuts of jeans? Check out this blog post: How to Wear Booties With Different Cuts of Jeans.
Shop Winter Boots
Highlights
- Linny H2O Boot: Great elevated casual option that is also water resistant! This tall shaft should work easily under basically any pair of jeans.
- Clemens Boot: Audrey owns this one and it works with every type of jeans, including straight leg ankle length jeans! The tall and narrow shaft is key. The low heel is easy to walk in, as well.
- Combat Boot: So cute for super casual style! The laces add texture and visual interest to outfits. Water resistant, too!
- Lug Sole Boot: This style works perfectly with sweatshirts + jeans + puffer jackets.
- Lug Sole Boot #2: This is a fan favorite. It also works perfectly with sweatshirt and relaxed sweaters + jeans + puffer jackets, in addition to slightly dressier casual outfits with wool coats. The shaft on this one is lower than the pair above, though, so consider that when trying to figure out how to wear it with jeans!
- Dressy Kitten Heel Boots: A must-have for dressing up for work or special occasions. Available in 3 colors and under $30!
- Suede Lace-Up Boots: These chunky-soled leather boots are a great option for casual outfits. Plus, they’re water resistant and come in 3 colors, including olive green!
- Block Heel Boots: Super affordable!
- Platform Boots: SO comfortable with great arch support. Available in four colors and are water repellent.
- Waterproof Boots: Insulated and waterproof with a cushy footbed. These cute boots come in 6 colors and are perfect for winter!
Remember to check out How to Wear Booties With Different Cuts of Jeans for guidance on pairing jeans with different types of boots!



