Why Choosing Expensive Travel Shoes Is Worth It

Why Expensive Shoes Are Worth it For Travelers

Comfortable travel shoes are very important, but if you’re like me, you’ll only realize that you need a new pair when packing a few days before (or day of) departure.

I’ve had my fair share of shoe mishaps while traveling and… I know that I’m not alone.

The perfect pair of travel shoes would have prevented my feet from feeling sore after walking 4.4 miles from the London Eye to the Tower Bridge. And waterproof boots would have been great when touring Iceland’s scenic waterfalls and glaciers – too bad my feet were wet for over 5 hours during that group tour!

After spending so much money on a bunch of misfits, I said enough was enough. I’ve searched for a new pair of winter travel boots and I’m so glad that I discovered Simons Shoes.

Simons Shoes has more than 100 years of experience selling shoes. Based in Boston, their shoes are not only trendy and fashionable, but many cater to a traveler’s needs. We’re talking waterproof, high-impact and shock-absorbent shoes – all the attributes that travelers need in a reliable pair.

The last thing we want is a pair of travel shoes that leaves our feet wet and achy. And let’s not forget all the times we had to leave our shoes behind because they were either too ripped or smelly to bring back home.


“The name of the game is finding a pair of travel shoes that are durable, comfortable and practical.”


After my shoe mishap in Iceland, I quickly realized that I needed a pair of waterproof boots that could withstand the elements. I also needed travel shoes versatile enough to wear wherever hiking the Cleeve Hill in England and exploring ice caves in Iceland.


“Since the possibilities are endless, my shoes had to keep up!”


I needed a pair of travel shoes that I could dress up or dress down, and a pair that was light enough to pack in my carry-on. With a growing list of requirements, I had to look outside my budget for quality products.

I recently got my hands on a pair of Bos & Co. Holding leather boots.

These bright red boots are trendy and I love that they make a bold statement for winter. Pricing at $220 USD, these are more expensive than the boots I would usually go for, but finding the perfect pair is about making a long-term investment.


Quality and Value

Invest in a more expensive pair of shoes for better quality. With a more expensive pair, you can expect that it will last, and in the end, it’ll cost you less.

In the past, I’ve bought cheap shoes to only regret it while traveling.

After a long day of walking all over a city, I’d have painful blisters on my feet. Inevitably, every winter I had to buy a new pair.

Buying the right pair once will save you so much more money in the long run than buying a bunch of cheaper, lesser quality pairs.



When picking out a travel shoe, the design is very important. A more expensive shoe is likely to have improved technology with an emphasis on comfort, versatility, and resilience.

Equipped with original Acquastop technology, my Bosi & Co. boots have a water-repellent breathable membrane that keeps both cold and water out. With every step, I can feel the softness of the wool instead of the hard insole, and the wool keeps my feet warm (really warm). My ankles feel supported and the rubber outsole prevents slips and falls.

I’m also a big fan of the stylish lace and side zipper which means that I can easily slip my boots on and off during airport security clearance. Other qualities to look for in travel shoes include memory foam insoles and breathable fabrics.



These high winter boots look great with a pair of dark blue jeans or leggings. I like wearing them with thick wool socks which combines style and comfort.

I’m heading to Italy in a few weeks and I will be wearing these throughout my trip and at the airport. My airport style is “comfort over everything” so I’ll likely wear these boots with a pair of dark blue jeans, a T-shirt, and sweater.

Here are other winter boots from the Simons Shoes collection that caught my eye.


 Gail by Bos & Co. lace-up winter boot, perfect for snow and slush.

Bestie by Bos & Co. sleek high heel boot, perfect for nights out.


Inga from Bos & Co. fashionable waterproof bootie, perfect for the fall and winter.



Simons Shoes Giveaway!

I love my pair of Bos & Co. Holding boots so much, that I’m giving a pair away! Giveaway closes Monday, November 28th.

a Rafflecopter giveaway


Thanks again Simons Shoes for the complimentary boots and for hosting this giveaway. Of course, all opinions are my own. 

Author: Danielle Desir

Danielle Desir is a Travel Finance Strategist that uses her financial background and knack for financial planning to empower those who want to travel afford travel and excel in their personal finances. She shares creative planning strategies, saving tips, cheap flight deals and even talks about her student loan repayment journey. Her financial expertise has taken her across the globe to over 22 countries and 3 continents (and counting), all while paying off her student loans, saving for a house, owning a home, and working full-time.

Want More Travel Finance Tips & Advice?

Get the latest travel finance content from Danielle!

Powered by ConvertKit


Why travelers should consider investing in more expensive travel shoes.