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Buying shoes online has never been easy, but thanks to our associate fashion editor Sierra Mayhew, now it is. She zips around the stores of New York City trying on all the trending shoes to report on the comfort, fit, and style so you never have to make a return again.

Navigating the endless collection of boots at Nordstrom can be very time consuming, but the worst part for me has always been the sizing. I’ve often found myself ordering the incorrect size or finding that two pairs of affordable boots I was excited about from the same exact brand fit me completely differently. All of this changed when I started my series If the Shoe Fits, in which I try out different shoes for style and size and report back on my sizing recommendations. 

Boots are a very difficult accessory for me because of how much space they take up in my small New York apartment. Last winter, my floors were flooded with boots, and this season, I’m capping myself at only one or two new pairs. That means the styles I choose need to do it all and be comfortable. From classic black boots to the latest trends, I’ve rounded up the boots I saw at Nordstrom that I think are actually worth investing in. You’re welcome.

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Nothing exudes luxury quite like the woven leather texture that has put many of my favorite It bags on the map. I have a few pairs of shoes from Paige, and they tend to be my most-worn pairs because they’re built for comfort. Were they comfortable? You won’t even know you’re wearing heels. How was the sizing? I went a half size up with these, and they were a bit roomy at the toes, but that just leaves room for more thick and cozy socks. There can be tension at the shin, so those thick socks will come in handy.

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It’s not often we see a footwear trend take over as quickly as the Miu Miu–inspired moto boots that I can’t turn a corner in NYC without seeing. Open Edit did its own spin on the trend, and it’s the perfect pair of boots to wear with jeans. Were they comfortable? Incredibly so. How was the sizing? I went with my true size, and there was a bit of extra room in this shoe. As previously mentioned, I love that for when I’m picking out a good pair of socks.

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Owning a pair of The Row boots is a fashion person’s biggest dream, so even slipping into this pair for a few moments felt like a treat. Flat riding boots have been all the rage as of late, and I’m loving them so much. Were they comfortable? I definitely wouldn’t consider them my most comfortable shoes due to some tightness at the calves. My calves are on the narrow side, yet I still found it difficult to slide out of these. How was the sizing? Stick with your true size. I tried these in a half size down and regretted it.

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Here’s another pair of riding boots for your consideration. I feel like whenever I wear brown croc shoes, I instantly get the fashion look that I’m after. Were they comfortable? Much more comfortable than a few of the other riding boots in my collection. How was the sizing? The definition of true to size.

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I recently was on a pretty serious hunt for a good pair of rain boots because I often find myself caught in the rain. Look good no matter the weather by choosing Toteme as your rain-boot brand of choice. Were they comfortable? The sole was incredibly comfortable, and they were so easy to slip on and off. How was the sizing? All I needed to say was my exact size, and they fit like a glove.

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I have an sixth sense when it comes to trend forecasting, and I’m telling you that combat boots will be the next to have a return. The best part of this news is a lot of people never stopped wearing theirs. Were they comfortable? Combat boots never fail me in the comfort zone. How was the sizing? Tory Burch is always true to size.

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It’s been said that this shade of oxblood is going to replace our love for the color red quickly, so act on it now. These slightly wedged boots are the way to go. Were they comfortable? The wedge made them so good for walking. Plus, you get the added height. How was the sizing? These are definitely true to size.

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The hippie inspiration continues with these platform boots that were absolute perfection. The quality of the leather was unmatched, and I’m still dreaming about them. Were they comfortable? I exclaimed after trying them that I felt like I was walking on the moon. There is actual memory foam cushioning at the sole, and it certainly made them worth the higher price point. How was the sizing? Another excellent example of true to size.

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These boots are so good someone came up to me while I was checking them out in the mirror and asked about where to find them. I made sure to try these on because they’re an absolute hit among Who What Wear readers, and I fell in love. Were they comfortable? I could walk for miles. How was the sizing? I went up a half size and felt that they were perfect.

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I have a pair of snakeskin boots that I hold near and dear to my heart. I once thought that nothing could make me want to replace them, until I tried on these Schutz boots. The main reason for the change of heart is the fact that they are seriously so comfortable. Were they comfortable? So comfortable and classic. How was the sizing? We’re on a true-to-size streak, and I’m loving it.

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I think everyone should consider a pair of black knee-high boots right now. They’ll quickly become your new best friend, going with you to everything from casual coffee runs to formal affairs. I was today years old when I found out this style comes in both suede and leather. Were they comfortable? Perfection. How was the sizing? Go up a half size in these ones.

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These shoes were like a disco ball for my feet. Everywhere I went in them, they sparkled from all angles. They’re the most beautiful shoes I’ve ever seen. However, they were also the most uncomfortable shoes I’ve ever worn and would require a private driver. I’ll keep dreaming about them, though. Were they comfortable? These are meant for door-to-door service for a seated dinner, but they might be worth it. How was the sizing? True to size.

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These boots caught my eye the second I walked into the store, and I love everything about them. The reason they ended up on the list of shoes that I wouldn’t buy is that while they are beautiful, so many other brands create similar shoes, and I’m not sure I could justify the hefty price point. I’ll keep them on my wish list. Were they comfortable? Totally! They have great cushioning, and I could pack them for a shopping trip. How was the sizing? I’m loving that they were very much true to size.

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I love these shoes, but I was just slightly unimpressed with them from afar. If you love designer snow boots, this is your moment, but I like to know I’m wearing something that won’t break my heart if it gets ruined. Were they comfortable? Yes, I’d suggest them for any snowball fight that lands on your calendar. How was the sizing? Pick your usual size.

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This post was published at an earlier date and has since been updated.

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