20 Stylish Ways To Wear Boots


In preparation for fall and the gorgeous, cozy fall outfits, I wanted to share with you 20 stylish ways to wear boots. (Fall, the best time of the year!) The outfit possibilities with boots are endless. This should give you style inspiration for the fall season so here is a collection of my favorite boot outfits that I’ve worn on the blog.

Boots are my preferred footwear during the fall. With the so many options available: over the knee, flat, heel, wedge, pointed toe, ankle, etc. there is a boot to go with every outfit style. There are boots for casual outfits, dressing up and work professionally.

Depending on your style and your personal preference a classic black or brown riding boot might just be the only boot you need this fall. But if you’re a boot enthusiast, like I am, then you’ll want to wear flat embellished ankle boots, heeled ankle boots in black and brown, of course some furry boots for the snow and so on.

In the fall boot outfits below you’ll see a variety of outfits with a variety of boots. You’ll also find a list with an outfit explanation and a link to more photos.

I turn to Sole Society when I need a new pair of boots or booties! I highly suggest you check them out if you’re looking for a pair of cute and affordable boots!

1. Wearing neutrals and cozy knits with brown ankle boots
One of the most popular outfits on my blog features a pair of gorgeous and perfect brown ankle boots from Sole Society. I wore an oversized turtleneck, matching blazer, belt and distressed jeans. Overall this outfit is very cozy and can be worn on a casual date or walk along the park.

2. Skinny jeans and a cape with brown suede knee boots 
Capes are one of the few items that only really can be worn a couple of months out of the year so I take full advantage. I wore brown suede boots with my favorite skinny jeans and an amazing brown cape.

3. Form-fitting dress with an awesome pair of black ankle boots
Be a little more daring with your fall outfit and go bare legged. A form fitting long sleeve dress with a rocking black leather jacket was the perfect companion to the black ankle boots.

4. Fair isle leggings and the coziest of scarfs with the cutest snow boots
Snow boots; more of a necessity than a fashion item but with the right pair they can be darn cute. I love cozy looking outfits when at the snow so it was only right to wear fair isle leggings with these furry snow boots.

5. Boyfriend beanie and burgundy jumper with a pair of black studded riding boots 
You can look stylish with a few essentials: boots, beanie, jumper, and jeans. This combination makes for the perfect fall outfit every time, just make sure the color coordinate.

6. Pleated mini skirt and a long overcoat with a pair of thigh high boots
With the right clothing combination, fall outfits can be sexy. I took a fun approach with these black suede thigh high boots and worn them with a black pleated mini skirt and long overcoat.

7. Cozy for the office with cropped burgundy trousers and matching gray knits
Boots can be appropriate for the office when worn with work appropriate clothing. Pair ankle boots with cropped trousers and a sweater, if it’s very chilly then add a scarf.

8. Grandpa cardigan and wool hat with flat embellished ankle boots
A fun approach to wearing embellished boots is with grandpa inspired pieces such as a long cardigan and shirt plaid scarf. Pair your cardigan and scarf with a wool hat and you’re good to go.

9. Classic riding boots worn with super skinny jeans and a dressy black blazer
Nothing is more classic than riding boots! A classic pair of black flat riding boots could be the only pair you need for fall.

10. Boots worn with the perfect pair of bootcut jeans
Of course let’s not forget boots worn with boot cut jeans. Find the correct length in a darker wash and pair it with a nice blazer and button down for a cute fall outfit.

11. An all black outfit with black riding boots 
If you want to channel Angelina Jolie and go with an all black look try wearing a long black coat, black turtleneck and black jeans with some classic riding boots.

12. A cute outfit for the pumpkin patch 
I mentioned that the holidays was one of my favorite things about fall and I love going to the pumpkin patch! Wear a cute and stylish outfit to find your favorite pumpkin for Halloween and wear brown boots with jeans. Add a splash of color to this pumpkin patch outfit with a scarf and hat.

13. Menswear inspired outfit with a feminine touch 
Channeling the menswear inspired trend try a pair of black ankle boots with menswear accessories; such as a boyfriend blazer and men’s watch.

14. Pair your neutral sweater dress with tights and suede boots
Suede boots and tights go and in hand so why not pair them and wear them with a neutral sweater dress and cozy cardigan.

15. Go casual and wear flat brown ankle boots with brown bomber jacket and tee
For a relaxed look wear cuffed denim jeans with low brown ankle boots and matching bomber jacket for a relaxed outfit that works for a weekend outdoors.

16. Fur snow boots and knits go hand in hand 
You need to stay warm and cozy in the snow so why not pair your very warm snow boots with leggings, a large sweater and oversized scarf. Make sure to wear your hair in a ponytail in case it starts to snow.

17. Brown suede boots and a white peacoat 
Play with length and try wearing your coat as a winter dress, top it off with a hat and suede boots.

18. Embellished ankle booties with a touch of color 
Embellished boots don’t need much reinforcement when it comes to the outfit, these beauties are the center of this look. Taupe flat ankle boots paired with bright green and blazer make the perfect fall outfit combination.

19. Pair rugged boots with pretty clothing 
A rugged outdoor terrain calls for boots that can handle the storm. Even though the top half of this snow outfit is cute the bottom half is snow proof.

20. Black over the knee boots with a rocking leather jacket 
For an ultra cool fall look wear your black over the knee boots with a black leather jacket and black skinny jeans. To soften up the outfit just a tad I wore a white knit sweater.

I hope these outfits have inspired you to wear boots in different ways and give new boot styles a try.