How to Wear Black Boots 21 Ways

I can almost guarantee that everyone has a pair of class black boots in their closet. Among the brown boots, colored boots, cowboy boots and knee high boots, there’s your trusty pair of black boots.

But are you stuck on how to wear them? Do you wear them the same way over and over again?

While there’s nothing wrong with wearing your shoes in the same way, I’m a believer that if you’re going to own something you better be able to wear it in more than one way otherwise it doesn’t deserve a spot in your closet!

Today I’m going to share a variety of stylish outfits to help you style your black boots in different ways.

I have a few different black boots below – Chelsea boots, wedge ankle boots, and over the knee boots. Hopefully this will help you create different outfits with what you have in your closet!

21 Ways to Wear Black Boots

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1. Denim Shirt With Shacket and Black Boots

denim shirt with shacket layered over

Shop the Outfit: Denim Shirt (Mine is super old – this one is similar) | Pants | Shacket | Boots

Go for a layered look! This one is super easy to replicate. Grab any chambray shirt in your closet, layer an oversized shacket over it. Pull on distressed black pants and black boots.

Check out more chambray outfits here!

 2. Black Boots with Denim Shirt and Vest

denim shirt with vest and skinny jeans

Shop the Outfit: Denim Shirt (Mine is super old – this one is similar) | Pants | Vest (sold out – similar here) | Boots

Vests are a great transitional piece for spring and fall! I love the different textures of this sherling vest and how the blue shirt pops underneath. The black boots and black denim jeans gives everything a cohesive look and feel.

3. Black Skinnies, Black Boots and White Cardigan

chelsea boots, jeans and cardigan

Shop this outfit: Cardigan Sweater | Pants | Boots

Probably the easiest way to wear your black ankle boots is with black jeans! This white button down cardigan goes with just about everything and I love it paired with a pair of skinny jeans and a pair of boots!

Depending on your own personal style, you can fold your jeans up so they hit right at the top of the boots or add a pair of cozy socks and pull them up over your pants!

4. Black Skinny Jeans, Boots and a Blazer

chelsea boots, skinny jeans and blazer

Shop this outfit: Blazer (sold out, similar here and here) | Graphic Tee | Pants | Boots

Heading to work? Pair those black boots with a blazer! If you’re office setting is a bit more professional you may want to swap the graphic tee for a button up or fitted neutral top but otherwise this whole look with the black skinnies and wedge boots is a great option for work!

Check out more chelsea boot outfits here!

5. Cropped Jeans and a Denim Jacket

cropped jeans denim jacket

Shop this outfit: Denim Jacket | White Tee | Pants | Boots

Black boots with cropped jeans? Yes please! Skip the blue skinny jeans and pull on some straight leg cropped ones! These cropped blue jeans look fantastic with a printed denim jacket with a simple white t-shirt under it.

6. Jeans and a Sweatshirt

cropped jeans and sweatshirt

Shop this outfit: Sweatshirt | Jeans | Boots

Need a casual outfit? Throw on a cozy sweatshirt! Sweatshirts and boots are a great look since the boot will give your look a bit more of an elevated appearance.

This look is still effortlessly chic with the perfect pair of Chelsea boots and cropped blue jeans.

Love cropped jeans? Check out more cropped jean outfit ideas here!

7. Sweater Dress With Denim Shirt Tied Around Waist

sweater dress with chambray top and black boots

Shop the Outfit: Denim Shirt (Mine is super old – this one is similar) | Dress | Boots

Yes, you CAN wear boots with dresses! You don’t always have to wear high heels! This black dress gets a fun upgrade with the chambray shirt tied around my waist and the cozy socks pulled up a bit at the top of the boots.

You could also swap the ankle boots for calf boots or over the knee boots if you want to show a little less leg!

8. All Black Sweater Dress and Black Boots

sweater dress outfit with black boots

Shop this outfit: Sweater Dress | Boots

Want a monochromatic look? Try black on black! Monochromatic looks are one of the seasons top current trends and this outfit is perfection.

A longer black dress with over the knee boots – this whole look just screams chic!

Check out more sweater dress outfits here!

9. Oversized Sweater Dress + Over the Knee Black Boots

sweater dress outfit with black over the knee boots

Shop this outfit: Sweater Dress | Boots

Maybe you love the chic look above but you prefer a more loose or shorter dress. Swap the fitted dress for a loose sweater dress! The thigh-high boots keep it appropriate with just showing a little bit of skin but still giving you a stunning look.

10. Oversized Sweater Dress + Combat Boots

sweater dress outfit with combat boots

Shop this outfit: Sweater Dress | Boots (sold out – similar here)

Want a bit of an edgier look? Switch the thigh high boots for combat boots! Keep your legs warm with a pair of patterned tights, or even cozy socks, and add combat boots to the look. Complete the look with a black leather jacket!

Check out more sweater dress outfits here!

11. Sweater Dress with Black Boots

chelsea boots and sweater dress

Shop this outfit: Sweater Dress | Boots

In warmer weather where you don’t need your legs covered, skip the tights and let your legs out! Black boots with less of a heel are always a great option when you’re wearing a short skirt or short dress!

12. Faux Leather Leggings + Over the Knee Black Boots + Denim Shirt

denim shirt with faux leather leggings and over the knee boots

Shop the Outfit: Denim Shirt (Mine is super old – this one is similar) | Leggings | Boots | Earrings (Sold out – similar here)

Boots over leggings are always a good option, especial in winter! Give your faux leather leggings an upgrade with black knee-high boots. Add a statement coat over the chambray top and you’re read to go!

(Want more over the knee outfits and tips to wear them? Head here!) 

13. All Black : Black Leggings and a Black Sweater

chelsea boots and all black outfit

Shop this outfit: Sweater | Leggings | Socks (similar here) | Boots

Another monochromatic look but this time, casual! The best way to break up an all black look without disrupting the vibe too much is in the socks!

A slight peekaboo sock above the top of your boots breaks things up a bit and gives this look an extra cozy vibe that’s perfect in cold weathers!

Love leggings? Here’s more faux leather leggings outfits!

14. Black Leggings, Black Boots and an Oversized Sweater

chelsea boots and sweater and leggings

Shop this outfit: Sweater | Leggings | Socks (similar here) | Boots

Not really into the all black look? I get it! Swap the black sweater for a tie die or printed sweater, keep those black leggings and black boots and you’re good to go!

15. Leggings and a Shacket

chelsea boots and shacket

Shop this outfit: Long Sleeve | Shacket | Leggings | Socks (similar here) | Boots

I shared another shacket look above, and here’s another fun way to wear it! Toss on a longer top to cover you butt, faux leather leggings and your boots for a great fall or spring look.

Want more shacket fun? Head to this post all about shackets.

16. Leggings and a Sherpa Sweatshirt

chelsea boots and leggings

Shop this outfit: Fleece Sweatshirt | Leggings | Socks (similar here) | Boots

If you need something cozy, cute, this is a best option! A cozy sherpa sweatshirt over leggings is always a cozy look. Throw on black boots with cozy socks and you’ll be the most stylish, comfy mom at school drop off!

17. Midi Skirt and Bodysuit

chelsea boots and black skirt

Shop this outfit: Bodysuit | Skirt | Boots

If you need more classic looks for the office, here’s another one! This midi skirt is a great option for ankle boots to keep things professional yet chic. Let’s be real, stiletto heels aren’t always the most comfy thing to wear all day at work so why not wear boots! This is a super cute, easy to wear look for the office.

18. Midi Skirt and Graphic Tee with Black Boots

chelsea boots and black skirt

Shop this outfit: Graphic Tee | Skirt | Boots

Heading out for drinks after work? I’ve got you. Swap the sleek bodysuit for a fun graphic tee! A super easy way to make a midi skirt less office and more date night is to simply swap a neutral top for a more fun top like this graphic tee.

You can also trying rolling the skirt or pulling it up a bit on your waist to reveal a bit more of your black boots! You’re ready for happy hour!

19. Black Boots, Midi Skirt and Henley

chelsea boots and midi skirt

Shop this outfit: Henley | Skirt | Boots

I love a good pleated maxi skirt and this green one is no different! The metallic vibe of it pairs nicely with the leather boots and the casual look of the Henley is great for heading to coffee or running errands!

20. Black Boots, Midi Skirt and Black Bodysuit

chelsea boots and midi skirt

Shop this outfit: Bodysuit | Skirt | Boots

Take that pleated midi and dress it up a bit! A fitted, all black bodysuit completely changes the look and feel of this outfit. A fitted seamless top gives this top a look that perfect for business meetings or dinner out!

21. Black Boots, Maxi Skirt and Black Bodysuit

chelsea boots and maxi skirt

Shop this outfit: Bodysuit | Skirt | Boots

This maxi skirt has been on repeat for me all year round – even with black boots! During cooler months, you can easily pull off this skirt by pairing it with a slim cut black shirt (again, like this bodysuit) and your Chelsea boots.

And there you have it! I hope these 21 different outfits styling black books in different ways inspires you to try out new styles for your own black boots!

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About Jen

Jen is a mom of 3 who loves frozen cookie dough, plants and a generous pour of creamer in her coffee. Her biggest joy is helping others find joy in their life, style and home through tips, tutorials and encouragement. She also runs 2 additional blogs. Feel free to send Jen a message or join the fun on Instagram!

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