If you know me, you know that I’ll never sacrifice comfort when it comes to cute shoes. Living in New York has given me the opportunity to walk everywhere, and I see that as a major privilege—I’d like to take advantage of the opportunity as much as possible. Regardless of my love for walking, I’m almost always in heels. Honestly, I don’t feel like myself in flats, so it’s important to me that I only shop for pairs that won’t leave me in pain in the middle of a fabulous evening.
My love for shopping online has occasionally left me disappointed in the sizing or structure of a pair of shoes, so this rhetoric inspired me to start my series If the Shoe Fits. I’ll be sharing what size to get based on how far I had to stray from my usual size. During my try-on session at Nordstrom, there were several pairs that I had to remove from my feet the second that I put them on because I just knew they were too uncomfortable to share with you here. With that in mind, allow me to tell you that I definitely can’t squeeze all 32 pairs of boots that I tried on into my New York apartment. So trust that the 15 below are actually worth the storage space.
Before I can even begin discussing footwear, my “outfit of the day” was too good not to share. This knit matching set was perfect for fall and made me feel like I was dressed up as a walking blanket. It has the ’90s-minimalist vibe that all of my co-workers are currently raving about.
My favorite part of this matching set was surprisingly the skirt because it was unlike anything I’d ever seen. All of my pleated skirts have been more structured, but this one is entirely knitted and so comfortable.
I recently watched a Bad Bunny interview where he discussed some of his greatest fashion choices over the years. He mentioned that he feels on top of the world and so put-together every time he wears a turtleneck. I completely agree. The best part about this knit is that you can wear it separately from the matching skirt anytime.
I contrasted the sophisticated ensemble with a pair of sporty sunglasses that made my look feel more casual. These are so lightweight I can wear them when I go on my morning runs and not feel at all uncomfortable.
I’m kicking it off with a pair of boots that I think everyone should have. Nothing feels more effortlessly chic than slouchy boots, and the color of these means they will go with absolutely everything.
Were they comfortable? They were very comfortable. The slouchy suede velvet made things even better. When I walked around the store in them, the soft fabric was absolute perfection. How was the sizing? Going up a half size made for the perfect fit.
While we’re on the topic of knee-high boots, I immediately wanted to snap a photo for Instagram of these Gucci boots that I tried out. The brand’s revived Blondie logo embellished the ankle in such a chic way. If I could buy a pair of designer shoes this year, this would be it.
Were they comfortable? These were so comfortable that I daydreamed of running out of the store with them on my feet. How was the sizing? Very true to size, which is something I find rare in European boots.
You know when you tell a joke that’s so good only a select number of people in your group get it? That’s a feeling that these boots remind me of. The beautifully crafted heel is a detail many would miss. Others would think you’re literally floating on air, as it nearly disappears in the right lighting.
Were they comfortable? I was nervous to try these on because the heel was a bit intimidating. They were a bit tight, but as they’re crafted from real leather, they’ll mold to your feet within one or two wears. How was the sizing? A true-to-size moment.
Brown never ceases to amaze me, and I absolutely love the way it looks with this pair of boots. The kitten heel feels like a great way to finish off a look for a more polished event, and I’ll wear my block heels in the evening.
Were they comfortable? In this pair of boots, I could walk about a mile to dinner. How was the sizing? My usual size ended up being perfect for me.
These Ganni boots have been hyped up by the fashion crowd for some time now, and I was excited to find out what they were all about. They’re perfect everyday boots, and I’d like to have them in every color.
Were they comfortable? Absolutely—I love that they also function as rain boots. How was the sizing? We love a true-to-size moment.
The ’70s have always had a special place in my heart, and these shoes have amplified that. Platforms have never steered me wrong.
Were they comfortable? It felt like there was memory foam at the soles. The shaft was a bit tight, but since they’re suede, that didn’t bother me too much. How was the sizing? I went up a half size and was glad that I did.
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.
I’ve never seen a more perfect pair of boots in my life. The thigh-high trend is destined to be a hit this year, and this is a pair of shoes that I think everyone should have the privilege of trying. They look best over a slim-fit pair of jeans or peeking out from under a skirt. A lot of thigh-high boots tend to fall down, but these stayed up the entire time I wore them around the store.
Were they comfortable? I didn’t even notice that they had a stiletto heel when I first got to try them out. How was the sizing? Going up a half size was a great idea.
These boots are so good someone came up to me while I was checking them out in the mirror asking 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.
I have been eyeing these boots on the Nordstrom website for weeks, so I am excited to finally be meeting them in person. While the cowboy-boot trend is starting to trail off, I would still go for the Western-inspired booties that simply give a subtle nod to the yeehaw attire that is still a major trend.
Were they comfortable? They were very comfortable for a pair of boots with kitten heels. It felt like I was wearing flats. How was the sizing? True to size.
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.
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.
I was in awe when I first tried these on. The very kitschy design made me feel like I was putting on a space suit since the shaft of these boots hugs the ankle so tightly. Regardless of the snug fit, I noticed no tension.
Were they comfortable? Most definitely. How was the sizing? I went for true to size and nailed it.
I couldn’t believe these boots were under $200. The stretchy material was as soft as skin and felt ultra-luxe. A pointed toe is always a nice touch, and I loved that they pulled in Western inspiration.
Were they comfortable? Oh, yes. How was the sizing? Don’t be afraid to go up a half size.
The perfect going-out shoes do exist, and they’re ultra-high platforms. The sales associate who helped me, Hannah, swears by them for a night out for added height without the discomfort.
Were they comfortable? They were a bit tight on me, but I was assured that they break in easily. How was the sizing? I’d suggest going up a half size at least.
These shoes were a walking disco ball. Everywhere I went in them, they sparkled from all angles. They’re the most beautiful shoes I’ve ever seen in my life. However, they were also the most uncomfortable shoes I’ve ever worn in my life 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.
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 because, 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 still 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.
These shoes are absolutely stunning. I just felt a bit shaky at the heel, so I am reluctantly being forced to pass on them. I can imagine them being the perfect fit for a nice Thanksgiving dinner but will have to leave them behind.
Were they comfortable? Yes, I just felt a bit unsteady when I walked in them. How was the sizing? I would go up a half size for comfort.
Now, this is what I call a good pair of shoes to wear at a party. The only reason I decided to pass on them is that I have so many platforms on my list and just don’t think I could squeeze them into my suitcase. But if given the opportunity to dress up as a disco ball, I just may have to give them a try.
Were they comfortable? Most definitely. How was the sizing? Go up a half size for sure.
It pains me that I won’t be taking these home, but there were a few similar styles in my collection, and I couldn’t justify them. They’re absolutely waterproof and require no additional spraying, though, so I have to recommend them to anyone who lives in a rainy climate.
Were they comfortable? For sure. How was the sizing? True to size and absolutely perfect.
I love these shoes, but I was just slightly unimpressed by 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.
For the quirky kids, these boots are unmatched. The bold design will make any outfit feel next-level cool. I’m investing in more timeless styles right now, but these were too fun not to include.
Were they comfortable? There was a bit of tension for me in the shaft, but besides that, I loved them. How was sizing? True to size.
