Footwear—they’re the bane of every women’s packing list. Or is that just me? No matter how many times I packed my suitcase, I always used to pause when it comes to the shoes, especially in the fall. Should I bring comfortable sneakers for active days and heavy, clunky hiking boots for outdoorsy bucket list adventures? Do I need a third pair of cuter, fashionable pair for all of those afternoons of museum hopping? The answer to all of the above is a pair of cute and comfortable travel boots.
Unfortunately, it seems incredibly difficult to come across the perfect balance of that ideal boot trifecta: comfort, style, and practicality. Difficult, yes—but not impossible.
My Pick for The Best Fall Travel Boots
Tall Riding & Knee High Boots
A tall riding boot is my go-to shoe for almost any cold-weathered trips—fall thru spring! The height keeps my calves warm, which is particularly helpful when they’re paired with a skirt. Plus, if you find some flat boots with a little tread, they can be used for light hiking too. Don’t forget to add some cute boot socks (like Modern Boho’s lace trim knee highs) or trendy boot cuffs for extra style and warmth.
1.
Eric Michael Montana
Eric Michael $108.97
Give your everyday style a subtle western touch with the Eric Michael® Montana knee-high leather boots, designed with adjustable buckle straps for that classic riding-boot look.
2.
Sofft Taryn
Sofft $259.95
These Italian leather Taryn tall boots are crafted in sleek neutral waterproof finishes, giving you a chic, effortless way to move through drizzly days without slowing down your style.
3.
Sofft womens Sharnell Heel Waterproof
Sofft $239.95
This customizable waterproof suede boot has a side zipper for easy on-and-off, a comfy cushioned footbed, a 2-inch stacked heel, and an adjustable lace-up back so you can tailor the shaft height and fit to your perfect shape.
4.
Women’s Hudson Shearling-Lined Waterproof Suede and Leather Boots
Overland $299
Step into ultimate autumn in luxury with our Women’s Hudson Shearling-Lined Waterproof Suede and Leather boots!Stay fashion-forward and weather-ready with these cozy, waterproof companions that will keep your feet happy and warm during the coldest fall days.
Western Inspired Footwear
Doesn’t everyone have a little cowgirl in them? I certainly do. And all of the ones below are cool country footwear. Warning, some have a bit of a heel on them, so I wouldn’t recommend for the cobbled streets of Europe. But, each are known for comfort, so they’re perfect to pair with a dress for a date night while traveling.
5.
The Annie
Tecovas $86.25
Meet The Annie, a best-selling tall cowgirl boot with a flattering 14-inch scalloped shaft, tonal stitching, and a fashion-forward snip toe—pairs effortlessly with everything from denim to dresses.
6.
IUV Cowboy Boots For Women Western Cowgirl Boots
IUV $53.57
Handcrafted with intricate embroidery and a layered, textured design, these women’s cowboy boots blend authentic Western charm with modern style.
7.
Spring Step L’Artiste Galop Boot for Womens
Spring Step L’Artiste
Hand-painted with floral embossing and crafted from naturally tanned leather, these ankle boots offer artful western charm, cushioned comfort, a smooth side-zip for easy on-and-off, and a wearable 2-inch heel that pairs effortlessly with everyday outfits.
8.
Alina
Bed Stu $295.00
Meet Alina, a leather ankle boot with a touch of western charm and city polish, featuring V-shaped inlays, hidden stretch goring, a walkable block heel, and a smooth inner zip.
Ankle Boots & Booties
Ankle boots are super stylish these days and might be the perfect choice for a little bit warmer weather where tall travel boots may seem out of place. They are also great when traveling to Asian countries like Japan where it’s a part of Japanese culture and tradition to remove your shoes before entering many places. You want something easy to slip-on and off!
9.
Heritage Lacer II Boot
Ariat $159.95
The Ariat Heritage Lacer II Boot is a tough and durable boot that is built to last. The boot is made of 100% full-grain leather and features a Goodyear welt construction for durability and flexibility.
10.
Ariat Wexford Waterproof Boots
Ariat $149.97 – $299.90
The Ariat Wexford Waterproof Boots are a great choice for anyone looking for a stylish and practical boot. The full-grain leather upper is both water-resistant and soft to the touch, while the durable rubber outsole provides excellent traction.
11.
Sofft Bridgett
Sofft $169.95
Crafted from waterproof Italian suede with seam-sealed construction, this AQUA Söfft boot keeps you stylish in wet weather with a wraparound strap detail, cushioned leather-lined footbed, inside zipper for easy wear, and a walkable stacked heel for everyday comfort and traction.
12.
BORN Women’s Kerri Ankle Boot
Born $74.30 – $242.76
The BORN Women’s Kerri Ankle Boot is a stylish and practical choice for any woman’s wardrobe. The upper is made of soft, supple leather that conforms to the foot for a comfortable fit, and the zip makes it easy to get on and off.
13.
Sofia Chelsea Boot – Women’s
Forsake $79.98
These casual Chelsea boots feature waterproof oiled leather and suede, cushioned memory-foam footbeds, and grippy traction for all-day comfort and durability.
14.
Comfortiva Rawnie
Comfortiva $139.95
Say hello to all-day comfort with the Comfortiva Rawnie. These sleek and supportive shoes are the perfect blend of style and cushioned bliss, making them your go-to choice for any travel occasion.
15.
Wexford H20 Boot – Women’s
Ariat $199.95
With a waterproof suede upper, a durable non-marking Duratread sole, and a lightweight ATS forked shank for support, these boots keep your feet dry and steady whether you’re out in the elements or on the move all day.
16.
Sofft Women’s Lonnie Black
Sofft $159.95
This stylish, adventure-ready boot features full-grain leather or Italian suede, a cushioned footbed with arch support, corduroy panels, a lightweight traction sole, and an easy inside zipper with a low everyday heel.
17.
SOREL Women’s Emelie III Chelsea Waterproof Boot
Sorel $119.99
Step into the spotlight with the Women’s Emelie III Chelsea Bootie—the sassy sidekick your vacation wardrobe has been longing for.
Motorcycle/Combat Style Boots
18.
Crave
TAOS $250
Craving comfort and style? This urban boot delivers both with easy lacing and a side zipper, cozy faux-fur and leather lining, and a supportive Curves & Pods® footbed that keeps city adventures feeling effortless.
19.
Women’s Bree Wool-Lined Waterproof Suede Boots
Overland $279
Meet your new travel essential—the Women’s Bree Wool-Lined Waterproof Suede Boots. Cozy wool lining and waterproof suede keep your feet warm, dry, and stylish.
20.
Born Moraga
Born $136.00
Say hello to perfection with the Born Moraga—stylish, comfy sidekicks that keep your feet happy and your steps confident all day long.
21.
Sorel Women’s Emelie II Lace Bootie
Sorel $95.99
Introducing the Women’s Emelie II Lace Bootie—your ultimate choice for style and comfort! Combining chic design with Sorel’s dependable quality, these boots strike the perfect balance between fashion-forward and practicality.
HIKING-INSPIRED BOOTS
I don’t know about you, but I think hiking boots are cute, so I wear them even when I am not on the trail! They can be paired with jeans, hiking pants or a pair of stylish leggings to fit many different occasions. Plus, most are super comfortable because they have a more rounded toe so you are not squishing your tootsies.
22.
ANJOUFEMME Casual Winter Hiking Boots For Women
ANJOUFEMME $45.99
These women’s snow-hiking boots deliver rugged protection with anti-skid, wear-resistant, water-resistant performance—making them a reliable partner for trekking, camping, and everyday outdoor adventures.
23.
Sabrina 20
Rieker $145
Stay warm, comfortable, and ready for winter in the Rieker® Sabrina 20 boots, featuring a water-repellent finish, cozy lining, durable stitch-down construction, lace-and-zip entry for a secure fit, a removable cushioned insole, and grippy traction for cold, wet days.
24.
PATRIZIA Women’s JADELYN Hiker Booties
PATRIZIA $69.95
These cozy winter booties blend city style with outdoor comfort, featuring faux leather, a sweater-knit collar, inner zipper, and weather-ready construction with a comfy lifted sole.
25.
Charlie Boot
Toms $95
This classic Chelsea boot in soft beige nubuck features CloudBound™ insoles for all-day comfort, delivering an easy, polished look that pairs effortlessly with everything from jeans to dresses—plus, it’s a style that gives back.
Don’t think that just because you are traveling that you will have to sacrifice cuteness for comfort or fashion for fit—you can absolutely have it all!
Ready to Start living your bucket? Use my Favorite Resources:
Finding Ideas
Of course this bucket list blog and my bucket list are great resources, but you can also use my free printable 2,000 bucket list ideas.
Naming Your List
Some people don’t love the term “bucket list”. But, what is most important is that you have a list, not what you call it, so here are 25 other names for a bucket list.
Storing Your List
I’ve created the perfect Google Sheets Bucket List Tracker Spreadsheet, that helps you store your list, plus keep track of all those checkmarks you’ll be making on it!
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