Cute Outfits with 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 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 0, 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 Naughty Monkey. They have a good variety of styles that are under 0, so if I want a fun pair of boots that are embellished or have fringe accents I like looking at what they have available. The embellished ankle boots and the black flat riding boots I’m wearing in outfits 5 and 8 are from Naughty Monkey.
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
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.
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.
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.
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.
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.
6. Pairing Boots with a Skirt
You can create a slightly sexy fall outfit if you combine the right pieces. I paired black suede over-the-knee boots with a black mini skirt, gray sweater, and long black coat. This outfit shows a little bit of skin, but it’s just the right amount. I didn’t pair thigh-high boots with this outfit because it just would have been too heavy with the long black coat.
7. Pair a Grey Sweater with Ankle Boots and Trousers
You can wear ankle boots to the office if you dress them up. It’s all about dressing appropriately for the office, and this can totally be achieved in the fall. I not only played with the items in this fall work outfit but also with the colors. I love how burgundy and brown looks together, so I paired brown ankle boots with burgundy ankle trousers and added some light color to it with a light grey sweater.
If it’s very chilly, add a color-coordinated scarf. In this instance, I wore a grey plaid scarf.
8. Combining Boots and Dresses
Again, I like to have fun with my fall outfits so for this look I went a little trendy and wore a pair of flat embellished booties with a dress.
I paired this black dress with a long sweater, scarf, and coordinating gray hat. If you like the style and can get away with it, I think pairing a dress with booties is a pretty awesome combination. It’s a little contradictory but is stylish when the outfit is balanced.
9. Classic Riding Boots and Jeans
I love a classic pair of flat riding boots; they are timeless and look stylish when paired with anything from jeans to equestrian pants. In this outfit, I wore these riding boots with dark skinny jeans. I “dressed up” the combination by pairing it with a burgundy silk top, black blazer and jersey scarf. This outfit is very rich in color, and it’s a classic fall outfit that you could wear for many occasions.
10. How to Wear Jeans with Boots
This might seem simple enough, just wear a pair of jeans and add on some boots. No biggy. But to get this combination correct keep these two style tips in mind: You need to find the correct jean length. You can’t have your jeans dragging on the floor, and they also can’t be too short.
You want your jeans to be about 1 to 2 inches from the ground; the jean should lay nicely on top of the boots. Of course, you should only wear bootcut jeans when wearing your boots under your jeans. It’s always best to go with dark- jeans as they make your legs look leaner. Light-wash jeans have a tendency to make your legs look larger.
11. All-Black Outfit with Flat Black 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 flat black boots. I kept this outfit intentionally sleek and simple.
Not much to it but a very cool outfit nonetheless.
12. What to Wear with Brown Boots
If you’re wondering what to wear with brown boots, then I’ve got the simplest answer for you. Pair them with dark wash jeans and add a splash of color to your outfit.
In this outfit example, I wore my tall brown boots with dark-wash skinny jeans, brown sweater, bright color scarf and burgundy hat. It’s always important to make your outfit interesting; this could be done with an accessory with some color, or both. As you may know, I love wearing hats, so my personal touch in this outfit was the hat.
13. Menswear-Inspired Black Boots Outfit
In this outfit, I channeled the menswear-inspired trend and paired black ankle boots with menswear accessories, in this case a boyfriend blazer and men’s watch.
The blazer has a looser fit and cute polka dot print on the inside. The feminine touch I added to this outfit was the white silk blouse, as I didn’t want this look to be entirely masculine.
14. Sweater Dress with Boots
Suede boots and tights go hand in hand so why not pair them with a neutral sweater dress and cozy cardigan. These slouchy suede boots have a naturally casual feel, so instead of trying to dress them up I wore them with a sweater dress and layered a long cardigan over it. This dress with tights and boots is a great fall outfit combination.
15. A Casual Brown Boots Outfit
For a relaxed outfit, wear cuffed denim jeans with flat brown boots and matching bomber jacket. A perfect outfit for a weekend outdoors. I wore this outfit while exploring Point Lobos State Reserve in California. If you haven’t been there you need to check it out; that place is fantastic.
I expanded on the white t-shirt and jeans look by adding a brown leather jacket and brown ankle boots. Overall this is a comfortable and stylish casual outfit.
16. Pairing Black Leggings with Brown Boots
Fur boots and knits go hand in hand so it’s only logical that this outfit would be perfect for the snow! You need to stay warm and cozy in the snow so 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.
This winter outfit has five different colors in it, but they all work very well together. You can’t always get away with pairing black leggings and brown boots, but in this instance it works. It might be because the black and the burgundy in the outfit dominate the brown, but in addition to having color balance this outfit also has proper balance. A form-fitting bottom half paired with a looser top half.
17. Pairing Tall Brown Suede Boots with a White Coat
This outfit plays with the idea of wearing a coat as a dress. The length of this coat just barely makes it O.K. to wear it as a dress. If you’re daring, give this outfit a try. You can’t tell from these pictures, but I also added a bright scarf to add some additional color to the look.
18. What to Wear with Taupe Boots
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, tan, and black make the perfect fall outfit combination.
19. Casual Brown Winter Boots
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.
I paired these brown winter boots with brown leggings, tan sweater dress, and white coat. A knitted beanie completes this winter outfit.
20. Skinny Jeans and Boots
For an ultra cool fall look wear black over-the-knee boots with a black leather jacket and black skinny jeans. To soften up the outfit add just a tad of white or a soft fabric like a knit. I wore a white knit sweater to add contrast and balance.
I hope these cute fall and winter outfit ideas inspires you to give different boots styles and outfits a try. I constantly try to share with you cute fall outfit with boots, make sure you take a look at my fall outfits for more ideas.