Cute Boots

Cute Boots

20 Stylish Ways to Wear Boots

by: Vanessa Rodriguez in StyleTweetShare2KPin82K84K Shares

20 Stylish Ways to Wear Boots - Visit for more outfit inspiration and style tips

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 cute outfit possibilities with boots are endless and this should give you plenty of outfit inspiration for the fall and winter season.

I’ve made this post a roundup of my favorite boot outfits that I’ve worn on the blog; everything from how to wear ankle boots to wearing booties with jeans.

Boots are my preferred footwear during the fall. With the so many boots options available—flat, over-the-knee, heeled, wedge, pointed toe, ankle—there is a boot to go with every outfit and occasion. You can wear a dress with boots, jeans with boots, and even ankle boots with trousers.

Depending on your style and your personal preference, a classic black or brown riding boot might just be the only boot you need. 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, some furry boots for the snow, and black suede over-the-knee boots.

Below you’ll find 20 example outfits that are paired with boots with an explanation of why each outfit works. If you want to see more photos of the outfit just click on the image or the link in the outfit title. By clicking, you’ll be directed to the original outfit post.

There are a lot of places you can buy a nice pair of boots. The boots I own came from a variety of brands.

Shopping for Boots

I love to buy brown boots or booties from Sole Society. They have many affordable options and new styles every year. Many of them are under $100, so they don’t break your boot budget, and they also last several years.

My classic riding boots are from Ariat. Their quality is exceptional, and they last a very long time. I like classic-style riding boots in black or brown with burgundy accents. You can see two ways I styled riding boots below.

For snow boots, I turn to Ugg. They are durable, well made, and they have some very fun options.

For some cute and trendy fashion boots, I like Vince Camuto, Sam Edelman, or Dolce Vita. They have a good variety of styles that are under $150, so if I want a fun pair of boots that are embellished or have fringe accents I like looking at what they have available.

For rugged outdoorsy boots that you would wear, say to a pumpkin patch, like the boots I’m wearing in outfit 12, I like CAT footwear. CAT initially just made work shoes, so you know these are durable.

For all other boot styles, I usually peruse Nordstrom. They have a ton of brands and every style you would want.

How to Wear Boots – 20 Cute Fall & Winter Outfits with Boots

20 Stylish Ways to Wear Boots - Visit for more outfit inspiration and style tips

1. How to wear Booties

One of the most popular fall 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 hanging out with friends. The blazer balances the distressed jeans, so there is outfit has a relaxed feel but not too casual. The oversized sweater is soft and relaxed, so the blazer works to bring structure to the look.

20 Stylish Ways to Wear Boots - Visit for more outfit inspiration and style tips

Note that the brown booties end near the thinnest part of my leg, this creates the illusion of longer and leaner legs. You don’t want booties to cut you off any higher than a couple of inches above your ankle because it can make you appear shorter.

2. Fall Outfit with Brown Suede Boots

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

20 Stylish Ways to Wear Boots - Visit for more outfit inspiration and style tips

3. Dress with Boots

You can be a little more daring with your fall outfit and go bare legged by wearing a dress with boots. A form-fitting, long-sleeve dress with a rockin black leather jacket was the perfect companion to these black ankle boots. The leather jacket plays on the black leather boots, and I kept the color scheme of the outfit pretty dark.

I love that these black ankle boots have a thick stacked heel and little tie accents near the top. The added accents bring personality to the style.

20 Stylish Ways to Wear Boots - Visit for more outfit inspiration and style tips

4. Leggings and Furry Snow Boots

Snow boots are more of a necessity than a fashion item for many, but with the right pair they can be darn cute.

I was trying to create an outfit that looked cozy and cute. I like the idea of fair isle anything in the winter, so I took advantage of the time of year, location, and wore an awesome pair of fair isle leggings and oversized winter scarf. The furry snow boots completed this cozy winter snow outfit.

20 Stylish Ways to Wear Boots - Visit for more outfit inspiration and style tips

5. Black Jeans Black Boots Outfit

These boots are a combination between biker boots and flat riding boots. I like that they are a little tough looking but still stylish. I paired these boots with black skinny jeans because I wanted to create one fluid line to make me look taller and leaner. Since the bottom half is form fitting, I was able to wear a looser sweater and top off this cute fall outfit with a gray boyfriend beanie.

Note the color coordinating in this outfit. Black, burgundy, and gray, not a lot of color but they look great when paired together.

20 Stylish Ways to Wear Boots - Visit for more outfit inspiration and style tips