Support TFG by using the links in our articles to shop. We receive a small commission (at no extra cost to you) so we can continue to create helpful free content. Thank you, we appreciate it!
Flat boots offer the best of both worlds when it comes to travel fashion. With a sleek appearance that’s easy to wear, they are a great pick for the style conscious traveler!
Best Flat Boots for Travel
Dr. Scholl’s Massaging Gel Insoles
How to Choose a Pair
Choose a chic pair that you can dress up or down on your travels, and always add gel insoles for maximum comfort while sightseeing!
Start by reading these general tips on choosing the best shoes for travel:
- 10 Steps to Packing the Best Travel Shoes
- The Importance of Packing the Best Shoes for Travel
- Don’t Break these Travel Shoe Rules
- Where to Shop for Comfort Shoes
In TFG’S top picks for Autumn/Winter 2018, we’re featuring ankle booties, knee highs, and a number of other cute styles to choose from! Pair them with jeans and leggings, or style them with tights and skirts for effortless style in your functional travel wardrobe.
When in doubt, you can never go wrong with a set of classic leather women’s boots. Keep the details to a minimum and avoid trend-driven accents if you choose an investment set that you can wear anywhere, anytime.
Here are a few articles to help you get started into your fall travels:
- How to Pack for Trips with Mixed Weather
- How to Layer Clothes
- Use a Summer Dress to Pack Light in Fall
- Best Shoes for Traveling in Spring and Fall
Packing Boots for Cold Weather Travel
Pack three pairs of shoes: flat boots, casual to dressy flats, and an additional set such as trainers or slip-ons depending on your destination and planned activities.
If it’s snowing, choose one of these options instead:
- Women’s Waterproof Boots You’ll Want to Wear
- The Best Waterproof Boots for Travel in Winter
- Womens Waterproof Leather Boots for the Rain and Snow
Keep reading below for a breakdown of the best flat boots for travel this fall through winter:
Reader Favorite
When we say something is a “reader favorite” on here, few products embody that sentiment better than the Simmens Boot from Ugg. Our readers are constantly raving about these versatile boots and we can see easily why! They’re known to be unbelievably warm and comfortable, making them some of the best womens waterproof leather boots for any cold climate travel. They also have replaceable sheep skin liner that keeps your feet toasty and dry.
Functionality aside, the Simmens boot has a sleek and stylish look that will beautifully complement the rest of your fall wardrobe. You can’t go wrong with this tried and true TFG essential!
Here’s the best women’s waterproof leather boots for travel!
Knee High
When it comes to fall style, few products embody the aesthetic better than a sleek riding boot. They’ll add an instant touch of refinement to your look while also keeping legs warm and toasty.
We love this classic option from Blondo (a huge reader favorite brand!) and can’t wait to pair them with our favorite skinny jeans! Throw on a peacoat and cozy long sleeve top to complete the look.
See more in our post about the best women’s leather boots!
Mid-Calf
Mid-calf boots are another fabulous option to rock this fall. Steve Madden’s “Troopa” boot keep feet stylish and secure with its edgy lace up closure. It also comes available in a variety of colors, meaning there’ll be a cute option for all.
For budget finds, take a look at this round-up!
Ankle
As every fashionista knows, ankle boots are synonymous with the fall season. And travel-wise, they are perfect for the style conscious woman looking for something sleek and functional to bring on her journey.
Comfort brands in particular never fail to produce cute styles! For something casual and perfect for everyday wear, opt for the “Villa” ankle boot from Blondo. Pair with skinny jeans or a sundress for your next day out sightseeing (and a bonus – it’s also waterproof!)
Read my review and find out why the Travel Fashion Girl readers and I love this comfortable boot for travel!
Leopard Print
Neutral ankle boots are a promising pick, but sometimes we want to have a bit of fun with our look. A boot in a bold leopard print is sure to do just that.
You can either go with the classic tan or rock an edgy gray rendition instead, which we find both unexpected and fabulous! Whatever you pick, just make sure to keep everything else simple. There’s a fine line between bold and overboard!
Not sure what clothes to use with them? Here’s how to wear ankle boots!
Waterproof
f your fall travel agenda includes rainy destinations, don’t forget to bring a sturdy pair of waterproof boots. With its trendy lace up design and sleek leather upper, the “Kesey” motorcycle boot from Ugg has once again made its way onto our list of top picks.
Tuck in some dark wash skinny jeans, throw on a waterproof jacket and you’re good to go!
Here’s a collection of the best waterproof boots for travel!
Cognac
Few shoes embody the fall aesthetic better than a cognac leather boot. We’re absolutely loving this classic pair from Sam Edelman! Paired with blue denim jeans and a crisp white button up, these boots will help curate the easiest, go-to fall getup.
You only need three pairs of shoes for any trip. Find out how with Pack Light Stylishly!
Slouchy
How cute are these? A fun, slouchy pair of boots is a great way to play up your fall apparel this season. This pair from Report does the job gorgeously, with a classic folded silhouette that will remain timeless.
In addition to its shape, we’re also loving the buckles and embellishments. Available in four fall-perfect shades.
Packing cubes make the perfect shoe bags to protect your luggage from dirty shoes. Take a look at other shoe bag ideas here!
Active Wear
Hiking in a cute pair of ankle boots? Yes, as a matter of fact, it IS possible! Few brands balance style and functionality better than Teva does. Their shoes take you from the trails to the town in ease and their Delavina boot is definitely one of our favorites.
Its waterproof leather upper protects feet from the elements while an adjustable strap ensures perfect fit. The best part? It’s actually cute!
What travel shoes do you use when you travel to cold destinations? Share in the comments below!
For more ideas on boots for travel, please read:
- The Best Waterproof Boots for Travel this Winter
- Women’s Waterproof Leather Boots
- Budget Friendly Autumn-Winter Boots for Women
- Gotta Have Boots for Fall and Winter Travel
I can’t find the UGG Simmens boot in a size 7 or 7.5 anywhere!! 😢
Hi Kelly, I am sorry to hear that 🙁 Let me look into this for you!
Did you find any size 7.5? Im looking for them also.
Hi Anna, I think they may have been discontinued as there appears to only be a small selection of sizes available. Have a look at this article for some other suggestions for waterproof leather boots: https://www.travelfashiongirl.com/womens-waterproof-leather-boots/ Sorry I could not have been more helpful 🙁
I first want to say I LOVE your website. I am leaving the US in August to study abroad in Ireland for about 8 months so your information has been very helpful! I was just wondering if you had shoe/ boot suggestions on what to bring to Ireland? I’ll be on the west coast where it is very rainy, so I’m just worried about buying pricey boots that may get ruined. Any suggestions would be appreciated!
thanks Danielle 🙂 I’ll post your question on the TFG facebook page this sunday to get more feedback for you: https://www.facebook.com/TravelFashionGirl
hope this helps!
Is it too unfashionable to wear my tall black leather boots in May in Paris? They are SO comfortable and would be great for the trip, but I don’t know if they will look too wintery by mid May. I have a few pair of ankle boots, but they aren’t nearly as comfortable.
Hi Joie, it will just depend on the weather. If it’s hot, might not be a great idea but if it’s cool or rainy, they’ll be perfect 🙂
Hi!
I’ll be travelling to Europe (Italy, Swiss, & France) in March. I’m thinking of bringing my calves suede black boots and my brown ankle boots. would it be enough? or too much? do you have any other suggestion? I’ve never been in western Europe before, so I’m not familiar with the weather there.
Check the weather before you travel but avoid suede if it’s raining. Leather boots are ideal. have fun!
What a wonderful website!! Such great, interesting and helpful posts!
thanks!
Thanks for this article! I love boots and I have some fake leather boots from DSW but I can’t see them lasting another season so I wish to upgrade to real leather. BTW, some of the links on the boots in your article from April are no longer available. Do you have any new style recommendations? Where’s the best sites to find good, comfortable leather boots?
hehe these ARE my new style recommendations: Fall/Winter ’13 😉 My best recommendation is to shop the expensive department after Christmas and New Years in January when they’ll be clearing out their boot stock.
I totally missed the link at the top. Thanks for pointing that out. I will also take your advice and hit the Macys at the end of the holidays.
P.s. Looking forward to a post about comfortable ballet flats!
I LOVE my flat knee high boots, especially when traveling through Europe. I can still look super cute without worrying about toppling over while running after the kids. Even better, I throw some gel inserts to cushion my feet and my boots feel as good as sneakers. Win for everyone!
Yes! 100% agree 🙂