The Search For The Perfect Winter Traveling Boot

In the months after I booked my flight from New York to Paris, I started thinking in terms of shoes. Being from the south, my closet is full of flip flops, ballet flats (Anybody heard of Repetto? I want some so badly!), sandals, high-heeled and knee length boots. Walking shoes of any sort were removed from my vocabulary the minute I finished high school P.E. for the last time ever. (Seriously. I handed over my thrice warn Sketchers to my mom and said "good riddance!" to the ugly shoes. I've been hiking through the woods in high heeled boots ever since. They just look prettier!)

Anyway, I learned the hard way in 2014 that when my European friends say they want to go hiking, they are serious. They don't mean walking through the woods on a snowy day and taking the path less traveled. (If they did, it would make all of the difference!) I knew I needed serious shoes. But not so serious, I convinced myself. It was only snow we were talking about. And we were going to be in cities. I didn't want to spend hundreds of dollars on shoes I'd wear once and never again; that's what you call wasting money. My poor husband – we spent every weekend for close to a month shopping for shoes. It was almost as painful as wedding dress shopping, although not quite.

The following are the shoes I decided on. Just thought you might like a little help if you need some new shoes. :)

I first bought a brown pair of these from DSW; then returned them and bought both brown and black on sale at Shoebuy for the same price as the one pair from DSW. They worked; they were comfortable enough. Steve Madden is a great brand and they make a fantastic shoe. As it turns out, lace up boots (even with zippers) aren't my favorite look. Especially without heels. I much prefer the Frye Parker Lace-Up boot (with heel) that goes all the way up to your knees if you are looking for a lace-up boot. Definitely check them out. I get compliments every single time I wear them. But if you are looking for a non-heeled lace-up boot, this one is pretty cute. And like I said – Steve Madden. It's like James Bond … only shoes. ;)

Remember how I said I get compliments on my Frye boots every time I wear them? When I spotted these at Saks Off Fifth, I knew it was meant to be. I was looking for a boot that could be worn with a dress and these were just them. I tried them on and took them home despite the over $100 price. If you think Steve Madden offers fantastic products, then you may not have met Frye yet. Frye boots are some of the best of the market. The leather holds up to everything and the shoes are oh-so-comfortable! 

Well, anyway … that's what I expected.

Because Saks Off Fifth sells products for cheaper than retail, there was no size listed in the shoe. I was assuming it was the right size, but it may not have been… Anyway, the very next day I put the shoes on to go for a short walk in the city. At first the only abnormal thing is that my socks kept sliding down – annoying, but whatever. Then, by the end of the walk I am in so much pain from a blister that has sprung up on my heal. That very moment was the moment I knew these wouldn't work for Europe.

But oh how I wanted them too!

My dad and Justin worked with me to try and figure out what was wrong. I used bandaids to try and break the boots in, moleskin … even added fur to the back of the shoe so that it would fit me better. None of it mattered though. I had 4 weeks to break these beauties in before I'd be walking my feet to death. Four weeks was just not long enough. I didn't wear them once while overseas. *sigh*

I know in time I will break them in. The only shoes I've ever owned from Frye that were comfortable upon first wear were my lace up boots. Even my flats killed my heals at first. I just have to give them time. 

And so, with that being said, I still highly recommend these shoes. They are gorgeous to a fault and since they were made by the amazing Frye brand, I know they will last forever. Now … time for some breaking in!

The last shoe I bought in my desperate search ended up being the one I wore most often during my travels.

Justin and I were meandering through Academy Sports just glancing through shoes since Justin was still trying to find me a pair of shoes with tread. I was being difficult, as always, and hating almost every pair he showed me. Then, jokingly (I think?), he pointed out these … which I also hated at first. "Seriously? People wear shoes with fur? There is no way I am ever going to wear Uggs or anything like that! They are uggggggly." And then, just for kicks, I tried these shoes on.




It was like putting on a pair of slippers. They were so, so, so soft. And the button? I decided it was cute. And maybe the fur would look nice with leggings and a dress… So we bought them. And I wore them out. All $30 worth.

After spending hundreds of dollars (well… $200) on shoes, I found myself liking the cheap $30 ones the best. Go figure. It was exactly the opposite of what I originally intended on doing.

Did I learn my lesson?


I still fully believe that shopping for shoes with my friends while on vacation would have been frustrating. I am just too picky. The only lesson I may have learned is to go to Academy first and try on the shoes Justin jokingly points out … just for kicks. Because you absolutely never know what you will end up liking the best.

What are your thoughts on shoes? Do you love shoe shopping or hate it? Have you ever bought shoes that you wanted so desperately to wear but they didn't work out? What about shoes you hated at first sight? Share! I'd love to hear your stories and know that I am not alone!

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