20 Stylish Ways to Wear Boots blue timberland boots outfit

20 Stylish Ways to Wear Boots by: Vanessa Rodriguez in Style

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 $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 Naughty Monkey . They have a good variety of styles that are under $100, 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.

Shop Boots

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.

Stay stylish, -V

ADD YOUR COMMENT Leave a Reply Cancel reply Your email address will not be published. Required fields are marked *


Name *

Email *


43 thoughts on “ 20 Stylish Ways to Wear Boots ” CalebX June 21, 2017 at 6:07 pm Reply

I must say you have high quality posts here. Your content should go viral. You need initial boost only. How to get massive traffic? Search for: Murgrabia’s tools go viral

Emma Braun May 21, 2017 at 11:14 pm Reply

You have shown some amazing ideas, I also love wearing boots and own many different pairs. This year I bought myself a pair of OTBT boots, https://www.otbtshoes.com/products/abroad-pecan-otbt . They looks amazing with most of my dresses, a great buy for boot lovers.

you November 28, 2016 at 6:57 pm Reply


It’s Fall Y’all! Southern Fall Style Must-Haves | Southern Bon Vivant November 16, 2016 at 8:16 am Reply

[…] ankle boots, duck boots—you name it—there is no such thing as too many pairs of boots. Luckily, articles like this one give some fresh ideas on how to wear your variety of boot […]

Dresses To Wear With Boots | clothingcharming.com November 14, 2016 at 8:18 pm Reply

[…] 20 Stylish Ways to Wear Boots […]

Brittney October 25, 2016 at 7:17 pm Reply

What brand are the brown booties in this pic the ones that appear to have the elastic band. There so cute I would love to know where to get them

Leanne October 22, 2016 at 7:31 am Reply

Very cute ideas but again, all skinny girls. What about those of us that don’t look that great in skinny jeans? Any ideas for boots other than the dresses?

Maribel October 15, 2016 at 7:19 pm Reply

Where did you get the boots in number 18? I love them.

afridiva September 1, 2016 at 2:31 am Reply

Combining these tips with the African -American style app http://www.needleplus . com will definitely be a win for me.

Thanks for the tips

Natali Griffin August 14, 2016 at 4:39 pm Reply

Great post!! Thank you for sharing all these ideas. I love your photos! You’re gorgeous!

5 Genius Closet Organizing Hacks To Finally Help You Dress Faster May 11, 2016 at 4:46 am Reply

[…] that you start with, working your way up. If the weather is freezing and you end up having to wear boots, your overall outfit options will be narrowed. If it’s a day for pumps and a dress, then […]

Tutorial Hijab May 7, 2016 at 4:09 am Reply

thank, it’s very help me

Graciela March 10, 2016 at 10:51 pm Reply

Style 20 is my favorite. A rocking leather jacket combines very delicate. Create a strong personality for me.


If you’re wondering how to wear booties and different style tips to keep in mind. - ARTICLES WORLD BANK February 8, 2016 at 7:58 am Reply

[…] might have come across my post, 20 stylish ways to wear boots, but if you haven’t I highly suggest you check it out. Out of the 20 outfits in that post, seven […]

Friday Favorites: 4th Installment - Save a Skillet February 6, 2016 at 1:28 pm Reply

[…] Fashion find: 20 Ways to Wear Boots Stylishly. Now that I’m getting close to my uuh, cough mid thirty’s.  I keep finding myself […]

How to Wear Booties - 12 Style Tips You Need to Know January 17, 2016 at 4:45 pm Reply

[…] might have come across my post, 20 stylish ways to wear boots, but if you haven’t I highly suggest you check it out. Out of the 20 outfits in that post, seven […]

How to Wear Boots with Jeans December 28, 2015 at 7:40 pm Reply

[…] Boots and jeans are a very popular and very stylish combination in the fall and winter time. I’ve shared with you tons of ways to wear boots before on my blog, check out 20 stylish ways to wear boots. […]

20 Ways to Wear Boots #fashion #style - Urban Angels December 18, 2015 at 2:50 am Reply

[…] Read More Source: – […]

3 Essentials to Make Your Fall Outfit 10x More Stylish December 10, 2015 at 9:10 am Reply

[…] If you need some boot outfit inspiration, you need to read my post 20 Stylish Ways to Wear Boots! […]

Why You Need a Pair of Over The Knee Flat Boots December 6, 2015 at 12:05 pm Reply

[…] If you’re looking for more boot outfit inspiration take a look at my 20 Stylish Ways to Wear Boots […]

red Light Ticket lawyer NYC November 23, 2015 at 9:54 am Reply

Traffic offenses cause factors oon your certificate, as well as points result uhjdftnm. gray timberland boots mensin increased insurance policy rates and even ceertificate abrogation.

Friday Favorites : Fourth Installment | Save a Skillet October 30, 2015 at 5:58 am Reply

[…] Fashion find: 20 Ways to Wear Boots Stylishly. Now that I’m getting close to my uuh, cough mid thirty’s.  I keep finding myself […]

Maddening Steve Maddens | justyouraverageshrub October 20, 2015 at 5:50 pm Reply

[…] http:///style/20-stylish-ways-to-wear-boots/ […]

Boot Season is Here! October 20, 2015 at 8:38 am Reply

[…] time of year calls for hayrides and hot apple cider in a giant mug. Your favorite boots come in handy when it comes to keeping you feet nice and cozy. The colder air makes you tired and […]

#1 life-saving tip for people who live alone! | funfitnessfoodfashionfiona October 13, 2015 at 1:01 pm Reply

[…] http:///style/20-stylish-ways-to-wear-boots/ […]

BOOTS!! | Tabitha's Blog October 6, 2015 at 10:18 am Reply

[…] http:///style/20-stylish-ways-to-wear-boots/ […]

Top Boot Trends For Autumn | Krisp | Blog September 30, 2015 at 2:44 am Reply

[…] You can’t make it through the autumn without a pair of boots. That’s just a fact of life so put down those suede shoes you’re looking at for a second and check out these latest shoe and boot trends for this season. Fancy feet, here you come! […]

Thinking about My October Fix | Struggles of a Healthy Foodie September 18, 2015 at 10:24 am Reply

[…] http:///style/20-stylish-ways-to-wear-boots/ […]

The Super Stylish Duo - Booties with Jeans September 6, 2015 at 5:30 pm Reply

[…] my outfits with booties, I usually have about 2 or so inches of my ankle exposed. It helps add some dimensions and keep the […]

How to Wear Over the Knee Boots August 24, 2015 at 9:15 pm Reply

[…] If you’re wondering how to wear over the knee boots with a shirtdress check out, How to Wear a Shirtdress this Fall. And if you want to know how to style a variety of boots year-round you need to read the post 20 Stylish Ways to Wear Boots! […]

Increase Website Traffic with these Strategies You’ve Never Tried August 18, 2015 at 11:20 am Reply

[…] traffic has passed organic traffic. The guest post links to the full article, 20 Stylish Ways to Wear Boots. That article on Stylishlyme is receiving the referral […]

Fall Outfit Series - Casual Riding Boots Outfit April 23, 2015 at 9:40 am Reply

[…] PS: Want some more boot outfit inspiration?! Check out 20 Stylish Ways to Wear Boots. […]

Boots Giveaway! January 4, 2015 at 7:30 am Reply

[…] know how much you love boots! 20 Stylish Ways To Wear Boots was the most popular post on my blog in […]

Tanya November 28, 2014 at 1:52 pm Reply

I like it!


Desiree November 24, 2014 at 1:55 pm Reply

Such great Fall/Winter outfit ideas to keep us looking great during boot season!

xoxo, Desi http://www.fashionlingual.com

Aldijana November 17, 2014 at 8:29 am Reply

So many great ideas and beautiful styles! Number 1 and 7 are my favorites, same boots, but different color combinations that just work great together!

Brittany November 6, 2014 at 5:29 am Reply

Really love this post. Great variation and the pictures are wonderful!! Pinned!

Emma November 5, 2014 at 8:33 pm Reply

Great post, thanks! Please tell me where you got your jeans in 01 and 15 – I love them.

Emma November 5, 2014 at 8:36 pm Reply

I checked your posts for the details and it doesn’t mention specifically. But I’m interested in your top favorite jean brands anyway!
blue timberland boots outfit

womens timberland 6 inch black boots
timberland classic 6 premium boot brown
timberland euro hiker boots navy
all black timberland boots with gold chains
timberland womens leather ankle boots Skip to navigationSkip to cartSkip to footer My Faves Promotions Easy Reorder Why Shop Jet? Track Your Order Free shipping on your first order! Free Shipping Over $35 & Free Returns Details Free shipping on your first order! Free Shipping Over $35 & Free Returns Details CATEGORIES Register | Log InEnter Zip Code Account My FavesEasy Reorder Easy Reorder My ProfileOrder HistoryShipping AddressesPayment MethodsLog Out Log In Register Enter your zip code My Faves Easy Reorder My Profile My Faves Easy Reorder Order History Shipping Addresses Payment Methods Log Out Cat Nav Need help? We're available 24/7. 1 (855) 538-4323 | help@ | FAQ Company About Us Careers Sell on Jet Jet Affiliates JetCares Tech Blog Download Social facebook twitter linkedin instagram Tips, Tricks, and Life Hacks Jet Blog Get the Offers email icon Sign up for our emails Feedback at sign icon Send us your feedback Copyright © 2017 Jet.com, Inc.  | Version: 3:958:1501021979745: Version: 3:958:1501021979745: Privacy NoticeTerms of Use

Black Timberland Boots For Men Outfit Sgxavtr

Download by size: 320x480 pixels / 640x960 pixels / 1024x1024 pixels / Full URL

How to downlaod: Click size above, after that you will open new tabs, right click Black Timberland Boots For Men Outfit Sgxavtr image and save image as, click save.

Random Wallpaper Hunter Boots Short Women 448 Views ★ ★ ★ ★ ★ Rate[ 0 / 0 ]: Hunter Boots Short Women , 0 / 5 ( 0 votes) Added: April 12, 2017 Upload by: Jessie Nike Basketball Shoes 2013 Releases 372 Views ★ ★ ★ ★ ★ Rate[ 0 / 0 ]: Nike Basketball Shoes 2013 Releases , 0 / 5 ( 0 votes) Added: September 12, 2015 Upload by: Jessie Mens Black Nike Tennis Shoes 223 Views ★ ★ ★ ★ ★ Rate[ 0 / 0 ]: Mens Black Nike Tennis Shoes , 0 / 5 ( 0 votes) Added: July 13, 2017 Upload by: Jessie Steel Toe Cowboy Boots Womens 277 Views ★ ★ ★ ★ ★ Rate[ 0 / 0 ]: Steel Toe Cowboy Boots Womens , 0 / 5 ( 0 votes) Added: October 18, 2015 Upload by: Jessie Contact Me Disclaimer Privacy Policy Sitemap Terms of Service

Copyright © footwearpedia | powered by wordpress