Are you obsessed with boots? We are! If you don’t already own a pair of chelsea boots you need to add them to your list. Take a look at our round-up of fifteen gorgeous styles!


Chelsea Boots

Written By: Niki Landry


There are a handful of shoe styles that surpass trends and become a classic wardrobe staple. The Chelsea boot is one of those styles, and it has the added advantage of being a perfect shoe to bring on your travels. 

Ankle boots are some of the best boots for travel in transitional seasons and cold weather. In fact, these are some of our top picks of the season!

The Chelsea is a type of ankle boot that’s simple but stylish, comfy, and versatile, making it a great addition to most packing lists

Keep reading for a detailed look at what makes the Chelsea boot a smart travel companion and a shopping list of styles to suit every taste.





Chelsea boots / Wide Fit Chelsea Boots


The traditional Chelsea boot is a pull-on style shoe characterized by elastic side panels, a suede or leather upper, and a low stacked heel. 

The boot shaft hits just above the ankle with a pull tab on the back. Its streamlined construction makes it a great complement for relaxed and contemporary outfits.



Vagabond Boot / Royce Boot


It’s a boot borrowed from the boys, and it brings a masculine element to your wardrobe. If you are looking for a boot to invest in or one that will stand the test of the time, look no further than a classic Chelsea boot.


Not sure which clothes to wear with them? Here’s how to wear ankle boots.





Hancock Boot / Vanity Boot / Nylie Boot


With many of the same characteristics as the classic boots above, these modern Chelsea boots have small changes or upgrades to suit different tastes and needs. 

A lower ankle shaft may be a better fit for shorter women, or maybe you are shopping for a boot with a taller heel or pointed toe. They still maintain the versatility, simplicity, and comfort of the classic, and if purchased in a neutral color such as taupe or gray, can easily be matched with many items in a capsule travel wardrobe.





Dulse Rain Boot / Stormy Rain Boots / Tinsley Rain Boot


The easy pull-on style of the Chelsea makes it a favorite shape for rain boots. The lower shaft and lighter weight, compared to traditional rain boots, makes it easier to pack and a smarter choice for trips where you know waterproof shoes are a necessity. 

Hunter boots are the popular choice for rain footwear, but these other styles can keep your feet dry at a favorable lower price point.  


Here’s our full round-up of the 13 cute rain boots in ankle-length!





Jara Boot / AEO BootSweet Boot


If your shopping budget is tight this season or you’d rather save your hard-earned money for your trip, the styles above are more affordable Chelsea boot options. It’s the same chic look for less money.

I’m particularly fond of the black pair with vented sides and wood block heel. These guys are low enough for extended wear, and can be easily styled with any fall or winter outfit. 

Overall, these styles may not have the life span of a high quality pair of boots, but they should get you through one or two seasons.


For budget boot finds, take a look at this round-up!





The Chelsea Boot / Carmen Booties / Newburg Boot


Expensive doesn’t always mean better, but you can usually expect a high quality of construction and materials with a pricier shoe. In addition to the leather wearing well, you can usually get high end boots repaired or resoled after extensive wear. 

When shopping for investment wardrobe pieces, it’s best to stick to classic styles and colors and shy away from trendy details or shapes.

The styles above would work for someone looking for a shoe they plan to keep and wear for years. The Cole Haan shoes have a waterproof coating without the rubber rainboot look, making them ideal for travel.


What do you think are the best Chelsea boots for travel? Please share your comments below!




For more tips on travel shoes, please read:

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Author Bio: Niki is an interior designer and artist from Louisiana. In addition to her design work, she writes for local and online publications sharing her experiences and passion for travel. Niki is currently adding stamps to her passport while building her design practice, Niki Landry Designs.


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