9 of This Season's Most Stylish Boots for Chilly Days ...

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I love winter, and that’s partly because I get the opportunity to wear stylish boots everyday! From knee high riding boots to military ankle boots, there are so many stylish boots available this season that you won’t know where to look first – why not buy several pairs to match every outfit in your wardrobe, and you’ll never have a bad-boot day again! Here are 9 of my favorite most stylish boots for this season that are perfect to wear, come rain or come shine.

1. Be Buckle Soon Boots in Brown

Be Buckle Soon Boots in Brown

These gorgeous ankle boots by ModCloth feature a light-brown textile upper with luxurious faux-fur lining and super-cool buckle straps that crisscross the boot, with a nod to military styling. Teamed with cargo or dark denim skinnies and your favorite jumper, they’re a great choice to see the new season in style. They have an explorer vibe about them that’s hard to resist, making these stylish boots one of my favorite choices for the winter!

2. Mix and Match Heel

Mix and Match Heel

These super-sweet Oxford style shoe-boots are made in Brighton by Poetic License, and they’re really fun and funky! With pretty coral-capped toes, chocolate brown houndstooth upper, orange and brown detailing and dark brown ribbon laces, you’re sure to turn heads wearing these. These unusual boots have a vintage feel that would look great with a pretty dress and opaque tights on chilly days – if you work in a creative environment, they would be perfect for work!

3. Lovable as Lychee Bootie

Lovable as Lychee Bootie

These little ankle booties by ModCloth are oh-so-cute! Bright, lychee red leather with a chunky decorative button and block heel ensure that these will see you through the winter with a smile on your face. I love the vibrant color and the retro feel the button gives, and would team these with black opaque tights and a cool pinafore dress for a 60's feel. But you could even wear them with knee socks if you’re feeling brave!

4. Speed Rumple Boots in Grey

Speed Rumple Boots in Grey

There’s something about these ModCloth boots that simultaneously screams ‘aviator’ and ‘pirates’ to me! You might not feel the same, but one thing is for sure, these stylish scrunch faux-leather calf boots are going to make your day instantly more stylish. Team with faded skinnies and an oversized t-shirt for an instantly cool weekend look – the dark grey finish and brass buckle straps add a vintage feel.

5. Steampunk Princess Bootie

Steampunk Princess Bootie

A little bit Victoriana, with a hint of steampunk, these ModCloth ankle boots are gloriously quirky, and I’ve had my eye on them for quite some time! Black and white faux leather combine with decorative black buttons and traditional stitching for a look that is elegant and cute. Whether you go for the full-on steampunk look in a long skirt and lacy blouse or tone things down with a pretty dress and opaque tights, these boots will help you stand out in a crowd – I love them!

6. Reading Curator Bootie

Reading Curator Bootie

Deep, dark blue is hot this season, and what better place to wear it than on your feet with these gorgeous sapphire ankle boots by Restricted? I love their deep blue suede finish, wedge heel and funky gold buckles that give these boots a really smart look. I would team with a shirt dress and matching blue bag, and think they would look great for a first date or afternoon shopping!

7. Just Trekkin’ in Boot in Stone

Just Trekkin’ in Boot in Stone

There’s something about knitted boots that’s so cozy and relaxing, and these foldover velvety boots by ModCloth are the perfect choice for cold, rainy days. Featuring a soft, velvety black outer and foldover ribbed black and white interior that’s really cozy, they look great with jeans and a shirt or even paired with opaque tights and a pretty skirt and jumper. They also come in burgundy, which is great if you’re looking to inject some color into your winter wardrobe!

8. Crossing Borders Boot in Brown

Crossing Borders Boot in Brown

A military style, lace-up knee boot will see you through the autumn and winter and is really versatile, adding a tough edge to pretty skirts and dresses or keeping you cozy when worn with skinnies and a jumper. I love these dark chocolate brown ModCloth boots and they’re made from Vegan faux-leather, so you can wear them guilt-free! Great for long winter walks or shopping trips in the rain.

9. Wildlife Biologist Boot in Brown

Wildlife Biologist Boot in Brown

These chunky, stacked-wood military inspired ankle boots by ModCloth are perfect for keeping out the winter chill, and I love their dark brown marbled finish which gives a worn effect and antiqued brass zipper. They would look lovely with dark skinny jeans and a chunky cable-knit jumper as the weather gets chillier, and I might invest in these myself as they’re versatile enough to go with a variety of different outfits!

I have several different pairs of boots for different occasions, from my trusty knee-high military inspired boots to western ankle boots and high-heeled boots that are great with pretty dresses. What are your favorite styles of boots and what will you be wearing this winter?