13 Cold Weather Friendly Outfits to Style Knee High Boots With

If you've ever met me, you would know that a staple for me of any outfit is my knee high boots. They're comfortable, fashionable, and go with literally anything. Literally the best part about women's fashion is knee high boots.

I like wearing knee high boots because I feel like they help break up an outfit and show off my legs better. Plus, they're so comfortable and extremely versatile, especially now that we're in the fall season and starting to get all of that cold and windy weather.

Now I'm not a fashion blogger, but I thought it would be fun to come on here and share with you guys some of my favorite outfits to wear with knee high boots. This is also a fun post for me to show you guys because in my fall content photoshoot a couple weeks ago, I got to practice my model posing and photography skills for this particular post and I think they turned out really well.

The dark brown boots in the photos below are from maurices. I bought them on sale this past February. I own most of the clothes in the photos so I will be adding what brands they are and where I bought them from and if I don't own them, I'll try to link to something similar so that you guys can go check them out.

Huge shoutout and thank you to Brianna, Sarah, Madison, Brianna, Dani, and Jordan who all modeled these outfits for me. You guys are amazing.

Enjoy!

This post contains a couple affiliate links from Amazon Associates. If you decide to click on or purchase something from one of those links, I make a little extra cash so I can continue to make more awesome content for you guys. I will only promote products that I use and enjoy at no cost to you.

Dress, Hat, and Leggings/Colored Tights

This is great outfit to wear if you are going out on a date or to have some drinks with friends and it's cold outside. I personally love wearing long sleeved dresses for a cute cozy fall look, but if you are trying to keep wearing your summer sundresses, this is a great look because you can just throw on a cardigan or a cute jacket to keep your arms and shoulders warm.

Leggings: Target Style

Dress: Similar dress found here

Hat: Similar one found here

Jeans, Fluffy Open Jacket, Black V-Neck T-Shirt

Are you going to a pumpkin patch this fall? Or maybe caroling for the holidays? Going for a winter stroll at your local downtown outdoor mall? This is a super stylish outfit that is warm and functional at the same time, which makes it perfect for outdoor activities. You can pair it with ripped jeans for a more casual look or with dark jeans for a more night friendly look.

Jeans: Similar pair found here

Jacket: Happily Thrifted

Shirt: Walmart

Sweater and Jeans

This is because it's a great build-upon look because once you've picked out your base, you can add whatever accessories you'd like. It's extremely versatile. For this look, we added a scarf for those cold fall days, but a couple necklaces or some statement earrings would also be perfect to add to this outfit.

Sweater: Similar one found here

Scarf: JoS. A. Bank Clothiers

Jeans: Similar pair found here

Long sleeve, Mini Skirt, and Leggings

This is one of my personal favorite looks for fall. It's simple to put together, but is perfect for a night out on the town, fall dates with your partner, or walks around downtown. It's comfortable, but still fashionable and beautiful.

Long Sleeve: Bittersweet Boutique

Mini Skirt: Amazon

Leggings: Target Style

Graphic T, Cardigan, and Jeans

This is a more casual look to wear with knee high boots and is for all of you who love to wear T-Shirts. This look is also better for more day-time cold weather activities because it provides comfort and style. You can also use the T-Shirt to provide a fun personal touch.

Cardigan: Target Style

T-Shirt: Target Style

Jeans: Similar pair found here

Long Sleeve, Vest, and Jeans

This look is a fun way to spruce up your sweater and jeans look by adding a vest! I personally love adding a puffy zip-up vest because I get so cold, but this fringe vest is a cozy and fun touch to any outfit!

Long Sleeve: Similar one found here

Vest: Similar one found here Jeans: Jeans: Similar pair found here

Crop Top, Leggings, and Oversized Flannel

This is another one of my favorite outfits to wear with my knee-high boots because it's perfect for all of the seasons. You can roll the sleeves of the flannel up for those warmer days or leave them down if it's a little chilly outside. It's a fun casual look you can wear while you run errands, go out to brunch, to a photoshoot with your friends, and more!

Flannel: Similar one found here

Crop Top: Charlotte Ruse

Leggings: Walmart

Peacoat, Dress, and Graphic Tee

If you're sad about not getting to wear all of your spaghetti strap summer sundresses anymore, this look is for you! Just start with a sundress as a base, throw a cute graphic tee and peacoat over it, add a fun fall hat, and voila! You have a super cute and fashionable outfit to wear on those chilly but not cold days!

Peacoat: Similar one found here

Graphic Tee: Target Style

Dress: Similar one found here

Sweater and Leggings

We can't forget about the classic fall go-to outfit! This is another great versatile outfit because you can make it as casual or as fancy as you'd like it to be! I personally like to add some dangly earrings to a tighter sweater, but a hat or a necklace are the best to go with my oversized ones.

Sweater: Happily Thrifted

Leggings: Target Style

Dress and Cardigan

Too cold for a sundress, but too hot for leggings underneath? Skip the leggings, throw on a cute cardigan, and rock those cozy vibes. This is a super comfy and cute outfit perfect for day time dates and brunch with friends. You can make this look as fancy or as casual as you'd like. If it's a little warmer out, just opt for a light jacket or roll the sleeves of your cardigan up.

Cardigan: Target Style

Dress: Francesca's

Black Jeans and Patterned Long Sleeve

This is a super fun outfit for those who live for patterns and shy away from plain colored tees and tons of layers in the colder months. I personally love stripes, but this leopard shirt is a super cute fall piece that is perfect for all of those outdoor activities that you just want to get a little extra fancy for.

Black Jeans: Similar pair found here

Leopard Shirt: Happily Thrifted

Leggings and a Holiday Sweater

I love fun holiday sweaters and this fun spooky ghost sweater is perfect for Halloween! It's super comfy and perfect for any holiday event. Plus, the best part about this outfit is that all you have to do is change out the holiday sweater for the next holiday and it works for all of the seasons!

Leggings: Target Style

Halloween Sweatshirt: Happily Thrifted

Midi Skirt and Off the Shoulder Quarter Sleeve Shirt

This is another one of my date or night out on the town with friends outfits for the fall. I like to add a necklace and some dangly earrings with this look because it makes such a simple outfit feel super elevated. You can tuck the shirt in for a more form fitting, fancy look or leave it untucked for a more casual vibe.

Long Sleeve Shirt: Amazon

Skirt: Similar-ish one found here

And there you have it! Some super cute outfits to wear with your knee high boots once it starts getting colder. I hope you had as much fun seeing all of the outfits we put together as we did trying them on!

Take a shot for the fact that I am not a fashion blogger and toast to all of the fun fashion shows I got to have during the process of making this post.

Cheers,

Kristaleagh