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Ankle boots—the perfect choice for the fall and spring seasons when the weather is transitioning between hot and cold. They can be worn with summer dresses as easily as they can be layered with sweaters and scarves. Here are a few travel outfit ideas for how to wear ankle boots when you travel in the fall!
Pair them with versatile dresses!
How to Wear Ankle Boots
Table Of Contents
Ankle boots are so stylish and timeless, an awesome addition to your travel capsule wardrobe. But sometimes they can be tricky to style. In this post, we’re sharing how to wear ankle boots in three key ways:
- in timeless tan
- in classic black
- in animal print
Find out how to wear ankle boots below!
Tips on What to Wear With Ankle Boots
Blondo Villa Waterproof Ankle Bootie
Choose a Neutral Color for its Versatility
If you’re only going to own one pair of ankle boots, make them a classic: a tan leather color. It’s the perfect neutral and easily matches with everything you own.
Tan leather shoes can go with just about anything, and this goes for ankle boots, tall boots, wedges, sandals, and flats.
The Blondo Villa pictured above is so popular among readers and the TFG Editor-in-Chief, we did a video review on them and a post.
Watch this video review on the Blondo Villa Waterproof boot!
They’re a much more versatile and fashionable option than a standard black pair of shoes. Just remember to choose a different colored purse for a stylish contrast.
Read our full Blondo Villa review!
Bag | Jeans | Tank | Boots | Jacket | Sunglasses | Bracelet
How to Wear Ankle Boots With Jeans – Neutral Color
Combine them with dark wash skinny jeans, a jacket layered over a tunic top, or long button up top. Alternatively, you could also pair with black leggings. Leggings can be worn as pants so long as your top is long enough to fully cover your crotch and bottom. Another option is to find legging style knit pants!
Where to wear: Columbus | Amsterdam | Portland
Shop more tan ankle boots: Nordstrom | Amazon
Here’s the list of the best skinny jeans according to our readers!
Blondo Villa Waterproof Ankle Bootie
Choose a Waterproof Ankle Boot for its Practicality
Waterproof boots don’t have to look dull and unstylish. Opt for a balance of fashion and function by choosing one of these styles that are highly recommended by our readers.
A timeless black boot such as the Blondo Villa pictured above will ensure you look fab anywhere from the streets of Paris to London.
You’ll want to look your best when you travel! Read my travel tips to Pack Light Stylishly!
Make Up | Necklace | Bag | Dress | Jacket | Boots
How to Wear Ankle Boots With Dresses – Waterproof Style
Pair them with a body con dress and a black faux jacket or a dark black trench, and ankle booties.
The Leith Body-Con Tank dress shown above is versatile and comfy for travel (just ask our readers!). Check out our video review on this awesome dress!
This video shows why the Leith dress works with boots or other accessories!
Where to wear: Moscow | London | Chicago
Shop more burgundy ankle boots: Nordstrom | Amazon
Here’s how to wear a leather jacket!
Choose a Print to Add Life to a Neutral Wardrobe
Alternatively, if you wear a lot of black and prefer a darker look, go for a bold pattern. Keep it monochrome with a black and white pattern or choose a leopard print which is considered a neutral print by many fashionistas—I agree! Gotta love a leopard print ankle boot or jacket to boost up a mostly black outfit.
Take a look at our list of the best chelsea boots for women on the go!
Earrings | Lipstick | Bracelet | Sweater | Bag | Skirt | Boots
How to Wear Ankle Boots With Skirts – Animal Print
Stick to a solid color skirt and a one-two outfit in general, unless you’re a master with prints.
Where to wear: Paris | Tokyo | Toronto
Shop more animal print ankle boots: Nordstrom | Amazon
Get tips and ideas on mixing prints!
How Editor-In-Chief Alex Rocks Ankle Boots for Fall Travel
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Comfort, affordability, quality, function and fashion – these are things that describe the perfect ingredients for travel clothing. And luckily for style conscious travelers, @toadandcoclothing makes all these things a reality! Check out the full review that TFG has done on this sustainable fashion brand, including what we think about their clothing and which items you'll want to add to your travel wardrobe. Link in bio to check it all out – don't forget to swipe right for more shots of my favorite pieces! #travelfashiongirl #ad
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Are you traveling to Paris this year? ⠀ ⠀ When in doubt, dress as the Parisians do. If you're looking to rock that effortlessly chic French look (with just a little bit of effort ?), throw on a stylish pair of ankle boots, keep your outfit's color palette neutral and always remember that less is more. Voilà! ⠀ ⠀ Style Tip: take a pair of shoes you can walk in comfortably all day and keep an ultra-cute pair in your bag for Insta-worthy moments!⠀ ⠀ Read Travel Fashion Girl's 10 Step Packing Guide for Paris in the profile link!
How to Pack Ankle Boots
Determining how to pack ankle boots for travel can be difficult, especially if you’re trying to pack light and avoid a shoe poking through a bag. To make it easier, start by choosing a container such as a shoe bag or a packing cube, then pack according to your type of luggage. The video below shows you more!
Watch this video to start learning how to organize with packing cubes!
Whether you have a front loading or top loading backpack, it’s crucial to put your shoes first, at the bottom. If you’re planning to pack shoes in a rolling carry-on, remember that it stands sideways, so it’s important to note how it functions when it is upright. Most often, your shoes will need to be packed close to the wheels, so that the luggage maintains its balance in transit.
To store, use washable shoe bags, gallon size Ziploc bags, or plastic shower caps to keep your belongings separate from your shoes.
We put together a five-part YouTube series showing the different methods to use packing cubes for travel. If you use this specific packing strategy, packing cubes can also compress your belongings. This is the secret to traveling carry-on only!
What are your tips on how to wear ankle boots? Share in the comments!
For more fall footwear tips, please read:
- Budget-Friendly Autumn Winter Boots for Women under $100
- Beat the Winter Frost with the Best Women’s Waterproof Boots
- How to Choose Hiking Boots
- Best Shoes for Travel: Don’t Buy Another Pair Until You Read This
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Alex, please do a post on pant length/style with ankle boots. I struggle with the length of pants and where boots should hit. Should there be space between jeans and boots? Should they fall right at top of boot? When do you tuck pants in? When do you roll pants? I am petite, so have many ankle/cropped pants, but also have floor length for when I wear ballet flats. Ankle boots sometimes look odd with both for me. The struggle for me on ankle boots is real! I have a bunch, but feel silly when I wear them. Everyone else makes them look so chic!
Thank you for sharing your feedback with us Nicole, we will definitely think about this when updating this post in the future! ?
Hi. Where can I find the Julian backpack that is in the picture with the Eiffel Tower. I have been looking everywhere and can only find a much smaller version… That does not work as well for traveling ?
Hi Robin, the RM Julian backpack is available in two sizes; the regular (or large) backpack and the slightly smaller medium backpack. I have the regular backpack, you can find it here: http://bit.ly/2Dbh12L. To learn more about the backpack, have a look at our review: https://www.travelfashiongirl.com/rebecca-minkoff-julian-backpack-review/ Hope this helps! ?
Where are the boots from that are in the featured picture?? Love the color!
Hi Katherine, I am afraid that the image at the top of the article is a stock image so we are not sure of the brand. ?
What booties or boots in waterproof leather would be right for a 60 yr old woman in Ireland/England in September??? Thanks
Hi Kathy, thanks for your question! We have a variety of articles featuring different travel boots. Take a look.
Hope this helps 🙂
Hi TFG, thank you for the cute ankle boot outfit suggestions. I am discovering how versatile ankle boots can be because of your articles. Thanks again!
I am also a very big fan of ankle boots, they are classy, easy to wear and suitable for different weather conditions, nowadays the ankle boot that I am liking the most is OTBT Lasso in red oak, its classy red color looks extremely stylish and make people turn heads, also being comfortable, they are just perfect for traveling.
Hi, please post a list for traveling to Dubai in early April.
Hi there, will add it to the list!
Tan shoes, black leggings, and navy jacket? I’ll just stick with black and grey. They go with everything I own.
Hehe, tan black and navy all match with everything too 😉
I’m with her…. I wouldn’t wear these three colours combined. Either the tan with navy or the tan with black… I hate navy and black combo most times unless there is a unifying element somewhere else (tartan scarf for instance). I know they are all neutral but I still can’t do it.
Everyone is different Meghan! These are just suggestions, find clothing that works for you! Thanks for reading!
Love the outfit inspiration of pairing navy jacket, black leggings and lighter ankle boots. It’s a great change-up for someone like me who plays it safe, black and gray palette. Love the punch of color in burgundy outfit too. Love your blog! My only disappointment is sometimes when I click on an outfit link, the item is sold out! Keep up the good work Alex.
Can you wear flat ankle boots with tapered pants (trouser for the Brits)? Anything that grips my thighs and upper calf physically hurts me — including bootcut jeans, which tend to be snug down to the knee before flaring out. So I live in loose cuts. Any hope of pairing them with a practical flat ankle boot, and not looking like a dude?
I think you could so long as the pants and shoes are feminine. A dressy trouser would work well. I’d say avoid jeans or casual pants for this style. Go for chic leather booties versus clunky boots. If I find some examples, I’ll post them in the comments 🙂